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Is Chicago Worth a Trip?

Absolutely! You may have heard that Chicago is dangerous. Yes, it does have its fair share of crime, so does any major city. It’s about being a smart traveler and being aware of your surroundings and you’ll have a good time. I

Chicago is the 3rd largest city in the US, and with two airports it’s incredibly convenient to get to. It’s been ranked “Best Restaurant City” by Bon Appétit magazine and the 2nd best city in the world by Timeout. Chicago has Midwest hospitality, it’s easy to navigate, there are tons of shopping and restaurants, it’s got a beautiful (Great) lakefront, and the list goes on and on.

How to Get to Chicago?

Since Chicago is located in the middle of the United States the city is easily accessible via plane, train, or automobile.

Chicago is home to two major airports. Chicago O’Hare is the larger and busier of the two airports and Midway is a little more manageable, although doesn’t have as many options. Both have the “L”, the elevated train rapid transit system, that runs directly from the airport straight into downtown if you want don’t want to deal with traffic.

Union Station in the West Loop is where the Amtrak arrives so if train travel is more your style it will take you straight downtown.

Check out my post on how to get around downtown Chicago.

Where to Stay in Chicago?

Since short-term rentals are legal, there is no shortage of VRBO listings to experience Chicago like a local, but I’m partial to hotels. Chicago has a ton of great hotels, this post has my full list of coolest hotels in The Windy City, and below are my top picks for your first visit.

The Langham Chicago | A 5-star hotel right on the Chicago river, it’s luxurious, has great views, and has a central location. If you need a little pampering the spa is amazing with great massages and hydrafacials!

The Drake Hotel | This 4-star hotel is rich with Chicago history, over 100 years old, but still feels as elegant as ever. Plus, it’s on the mag mile and Lake Michigan. Try the high tea in the Palm Court during the day, or cocktails and dancing at Coq D’or.

Viceroy Chicago | This is where the cool kids stay! It’s a 5-star hotel, with a great location, and an outdoor rooftop pool (need I say more).

Day One | Chicago 101

Day:

Start the day strong with brunch at Etta. Etta is a modern Italian restaurant and one of my favorite dinner restaurants in Chicago, but brunch is equally amazing. Do not miss the focaccia with whipped ricotta and get a pizza for the table, just trust me on this one. Etta has two locations but for this itinerary you’ll go to the River North location.

After brunch take a Lyft to Navy Pier. Yes, it is touristy, but you’ll get a great view of the city and you can’t visit Chicago without taking a ride on the Ferris Wheel (it was built for the Chicago World’s Fair after all). Navy Pier is also home to Offshore Rooftop, the largest rooftop deck in the U.S. If you are going to Navy Pier just for Offshore though I recommend you check out the website first as they are often closed for private events.

Now that you’ve experienced a little bit of the lake, it’s time to check out the river. Take a Lyft to the corner of Michigan Ave and E Waker Driver for an Architectural Boat Tour from the Chicago Architecture Center. You may not know about Chicago architecture before arriving, but you’ll be surprised at how rich with architectural history Chicago is.

When the tour is over, walk along the Chicago Riverwalk on the Chicago River. It’s a little over a mile long but you don’t need to walk the full length. There are bars and restaurants to stop along with a way to get a glass of wine, a snack, and do a little people-watching. The soft pretzel at Northman Beer & Cider garden is actually pretty good!

Night:

You can’t come to Chicago for the first time without trying deep-dish pizza. My favorite place that is the most accessible is Lou Malnati’s, and they just opened a location on Michigan Ave! Get the butter crust, get the Malnati’s salad, and thank me later. But you had pizza with brunch and now dinner you say? Welcome to Chicago.

Finish your night at The Second City, the world-renowned sketch comedy and improv club. I like to go to the latest show, the comedy is a little looser then. They offer a few different shows so read the descriptions and pick which one is most interesting to you. With talents like Aidy Bryant, Tina Fey, and Steve Carrell coming out of it, you can’t go wrong with any choice.

Day Two | Bougie Chicago

Day:

I hope you aren’t afraid of heights because Willis Tower, locally known as the Sears Tower, has a Skydeck that everyone must visit at least once. It’s the third tallest building in the Western Hemisphere, but the real star of the show is The Ledge. The Ledge is actually a glass box you stand in that goes 4 feet out from the building, and is 103 stories high. Cue stomach drop.

Now that your stomach is settled time for brunch and some more amazing, although much more manageable, views at Cindy’s Rooftop on Michigan Ave. The rooftop has a retractable roof and a terrace (with firepits when it’s chilly) so you can dine no matter the weather. The view is of Lake Michigan, Millenium Park, and “The Bean”, your next destination.

Cloud Gate, aka “The Bean” is located in Millenium Park and is quite a tourist destination. Truth be told, it will be busy and you won’t need much time there, but you have to at least check it out.

Take a five-minute walk to The Art Institute of Chicago, one of the country’s oldest art museums, and check out the works of Van Gogh, Monet, and Picasso

Night:

Get ready for a night on the town!

In the Midwest we know steak, but that doesn’t mean you need to go to an old-school steakhouse. Maple & Ash is a scene, is the best possible way. You’ll drop a pretty petty here, but the vibe is cool, the food is amazing, and you’ll feel like you are celebrating something, even if it’s just going on vacation!

The Chicago Magic Lounge is a hidden gem because it’s not in a part of town where tourists go, but it’s a local favorite. Enter through a faux laundromat and enter into a Gatsby-era speakeasy lounge with a close-up magic show. It’s an experience unlike I’ve had anywhere else.

When to Visit Chicago

Chicago is a city with four distinct seasons and they all have their high points, but nothing compares to Chicago in the Summer. Spring and Fall are also really great, but you risk a bit of rain in the Spring or an early cold front in the Fall.

If you chance it and come in Winter you’ll have to substitute some things on the itinerary (let me know if you do and I’ll give you recommendations) and don’t be surprised if your flight is impacted by snow.

Only 1 Day in Chicago?

If you only have one day in Chicago (boo!) do the Day One itinerary. It really is Chicago 101. If it happens to be raining on your one day in Chicago, sub the day portion of Day Two and stick with the night portion of Day One.

What is There To Do in Chicago For 3 Days?

Wondering how many days are needed in Chicago? I prefer two nights, three days the first time I visit a new city. That way I have one full day and night that isn’t a travel day, but if it’s not for me I haven’t committed too much time. You’ll get to see a lot of Chicago in this time frame and won’t be bored.

I have separate itineraries for the Spring/Summer and Fall. Let me know in the comments if you’d be interested in a Winter itinerary too.

Some people ask if 2 days is enough in Chicago. I love The Windy City so I’m partial, but if the option is 48 hours or nothing, definitely visit and you’ll get a good feeling for the place. If you are here longer though you won’t be bored.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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Downtown

Avec

You can’t go wrong with Avec, and now they are open for brunch it’s a must-visit! Avec serves Mediterranean-inspired tapas and there is something (multiple things) for everyone. The food is fresh, flavorful, and delicious. It’s one of my favorite spots in the city.

Beatnik

I haven’t been yet, but this has the coolest bohemian vibe and is right on the river. There’s a terrace (enclosed in Winter), DJs, Mediterranean food, and fun brunch cocktails. It has a great reputation in the city.

Wildberry Pancakes & Cafe

This is the only pick on the list that doesn’t offer alcohol, but you can’t think of pancakes in Chicago without thinking of Wildberry. They have a massive menu with all sorts of pancake options, but if that’s not up your alley they offer lots of egg dishes too. Or get the best of both worlds and order an egg dish with a pancake on the side. They don’t take reservations and are wildly popular, so prepare to wait or get there early.

Cindy’s Rooftop

The reason you go to Cindy’s is for the retractable roof (which means you can go in when it’s not warm) right on Michigan Avenue with unmatched views of the bean. I mean…don’t discount the food, but you won’t get that view anywhere else.

Maple & Ash

One of my absolute favorite dinner restaurants, but I have yet to make it for brunch. When you are here it’s for a celebration. It’s pricey, but if it’s anything like dinner you will not regret it. It’s a scene at dinner, but a little more laid back during brunch.

Lincoln Park/Lakeview

Summer House Santa Monica

Like The Hampton Social, Summer House has a coastal vibe, but this time it’s California cool. Less fish on the menu, this is really all about laid-back American food. Fun fact: one time I went here for brunch and was wearing the same exact white and blue gingham shirts as the employees. That was fun!

Café Ba-Ba-Reeba!

Café Ba-Ba-Reeba is one of my favorite tapas places in the city and brunch tapas do not disappoint!

Blue Door Farm Stand

Farm-to-table classic American food with a French countryside aesthetic. I like to think this is what it’s like dining with Ina Garten.

Farm Bar

Midwest through and through, Farm Bar has an elevated take on comfort foods. Think Nutella croissant, pork belly poutine, and apple brandy maple syrup.

Little Goat

Stephanie Izard is high on the list of Chicago culinary icons and Little Goat is her version of a diner. Open Tuesday-Sunday and only until 3:00 this is a great option if you are visiting Chicago during the week. It’s also a much more affordable way to try Stephanie’s (did I mention she is a James Beard recipient) food than her other restaurants Duck Duck Goat and Girl & The Goat.

Related: 3 Day Chicago Itinerary for Spring and Summer

West Loop

Beatrix

Beatrix has a few locations around the city but my favorite is the Fulton Market location in the West Loop. Of course, they have indoor seating but they also have a ton of outdoor and I may love eating al fresca as much as I love eating brunch. Whether you want to go healthy or not so much, Beatrix has plenty to choose from. Hot tip, I always request my coffee in a to go cup up front so I can walk out with it once finished with brunch. Never not with 3 beverages at all points in time.

Bandit

They like to say they are “farm-to-bar” and they have a bottomless brunch to back it up. I haven’t made it here (yet) but the menu looks like it would be great for after a night on the town.

West Town (Wicker Park, East Village)

Lonesome Rose

The best Tex-Mex place in the city (I think it might be considered Logan Square or Bucktown actually) their queso is amazing as is the breakfast burrito. If it’s nice when you visit make sure to get a rooftop spot!

Paradise Park

Paradise Park is a fun spot any time of day, but do yourself a favor and go to the roof and find yourself an old-school patio chair to sit in. They could do well based on the gimmicks alone, but the cocktails are great (my last was topped with a mini donut) as is the breakfast pizza.

Parson’s Chicken & Fish

From the same group behind Lonesome Rose, Parson’s Chicken & Fish is known for its fried chicken, frozen boozy drinks, and amazing outdoor patios. They have a few spots in the city, but my favorite is the West Town location (although Logan Square is the original and has more outdoor space).

The Perch

A classic American brunch spot with indoor, outdoor, and beer garden seating, The Perch also has a wood-fired grill for various dishes. The blueberry cornbread and hashbrowns are some of my must-try recommendations.

Etta

Like Maple & Ash, and from the same group as Maple & Ash, Etta is one of my favorite dinner picks but I haven’t made it to brunch yet. Trust me, it’s on the list. They have both a River North and a Bucktown location but I love the roof at the Bucktown spot (you know how I love a good rooftop!) The focaccia at dinner is amazing so I can only imagine what it is like at brunch with jam and I love the wood-fired pizza for the table.

Cracked on Milwaukee

Cracked is the place you want to be when you’ve had a little too much fun out on the town and are looking for a breakfast sandwich and some tots to accompany your mimosa flight.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide. If you are visiting in the Spring and Summer, don’t miss out on that 3 day itinerary which includes the Lakefront.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Day One | Today is all about Downtown Chicago

Day

A great place to start the trip is Cindy’s Rooftop (don’t worry, it’s covered in the Fall).  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, take the 5-minute walk to the Art Institue of Chicago. You’ll walk right past the Bean, whose real name is Cloud Gate, and into the second-largest art museum in North America (right behind the Metropolitan Museum of Art in New York).

Related

• Best Hotels in Chicago for every Neighborhood
• Coolest VRBOs in Chicago
• Best Brunch in Chicago

Night

Take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. They are known for their steak, and it’s not to be missed, but everything is amazing. It’s a scene so take the opportunity to get changed and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail, it’s a great spot for people-watching.

After dinner, get back in the Lyft because you are going Uptown to one of my favorite spots in the city, Chicago Magic Lounge. You’ll enter through a faux laundry storefront and enter into a speakeasy-like close-up Magic Show.

Day Two | Enjoy the city like a local!

Day

Inside the Restoration Hardware in the Gold Coast is the beautiful 3 Arts Club Cafe and it’s a wonderful spot for brunch in the Fall. With its tall ceilings and tons of glass windows, you get the sense of outside but you’ll be warm and cozy before heading out for the day.

Depending on the weather you can grab a Lyft or go for a nice stroll to Lincoln Park and the Lincoln Park Zoo. It will be about a 20-minute walk to the Zoo, but you’ll hit the park after about 10 minutes from Restoration Hardware. If you aren’t sure how much time you’ll spend it’s still work visiting because it’s totally free! Some of my favorite animal exhibits are the Big Cats (they just came back after some time away for a habitat renovation), the Primates and the Bears (I just realized that was very close to Lions, and Tigers, and Bears, oh my!)

Night

You’ll dine in the Lincoln Park neighborhood and have dinner at Summer House Santa Monica, a West Coast-inspired fresh-fare restaurant. And it’s not too far from this evening’s entertainment…Second City!

If you like comedy then I’m sure some of your favorite comedians have spent some time in The Second City. That’s because it’s a world-renowned improv and comedy club that’s been around for 60 years. They offer a variety of shows on different stages so take a look and I’m sure they’ll have something to appeal to you. I’m partial to the late shows because I prefer them just a little more ‘adult’ but you do you.

Related: What to do in Milwaukee ( a quick trip from Chicago)

Day Three | Becoming a fan

Day

After two substantial brunchs, it’s time to grab a quick coffee and a pastry before you see Chicago from a different view. Depending on where your hotel or VRBO is will probably depend on where you’ll go. Some that I love are Goddess & the Baker, Big Shoulders, and Fairgrounds Cafe.

Next is the Skydeck at the Willis Tower (or as we locals still say, the Sears Tower). At 103 floors, it is the highest observation deck in the United States. If you dare, step into one of the glass boxes overhanging the building as you look down more than 1,300 feet to the ground. It’s a little terrifying, but not something you can do every day.

Then you are off to watch the Chicago Bears play some football at Soldier Field (notice I didn’t say win, I like to be realistic). Since it’s an outdoor stadium with no retractable roof, make sure to check the weather before you come to Chicago so you can pack appropriately.

Night

You can’t visit Chicago for the first time without trying deep-dish pizza. Love it or hate it, you at least need to try it, and that’s what’s for dinner.

Take a Lyft after the game and go to Lou Malnati’s. If you are visiting with enough people to order two pizza’s then you may want to get one deep dish and one thin crust, because it’s pretty good too since it has their signature butter crust. If you are craving some produce in your life the Malnati Salad is so good.

Day drinking always makes me tired (and I typically have a drink at sporting events) so I would call it an early night, knowing tomorrow is a travel day.

Related: Best Hikes Near Chicago

I hope this has been a good starting point for your Fall itinerary for Chicago.   This is by no means exhaustive and will depend a bit on the weather. If it happens to be a really nice day, I recommend an architectural boat cruise on the Chicago River or perhaps a walk along the lakefront. If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Make sure to check the weather and the sports schedule to see if you need to make any adjustments.  

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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Lakefront Trail

• Location: Chicago, IL
• Distance from Chicago: 0 miles
• Driving Travel Time: 0 minutes
• Trail Distance: 18 miles
• Hiking Difficulty: Easy
• Entry Fee: Free

You literally do not need to leave Chicago to go on a long, beautiful walk. Luckily for us, those in charge of running Chicago years ago decided that the lake should be enjoyed by everyone, which is why 18 miles of Lake Michigan lakefront is a park, complete with walking and biking paths.

Waterfall Glen Forest Preserve

• Location: Dupage County, IL
• Distance from Chicago: 25 miles
• Driving Travel Time: 25 minutes
• Trail Distance: 11 miles
• Hiking Difficulty: Easy
• Entry Fee: Free

One step into Waterfall Glen and you won’t believe you are less than 30 minutes outside of the city. Completely immersed in the wilderness there’s not one skyscraper insight or city sound to be heard. The name might be a little misleading because the waterfall is a small manmade one so don’t set your expectations too high, but the miles upon miles of trails for walking, biking, and horseback riding make the short trip well worth it.

Indiana Dunes National Park

• Location: Porter County, IN
• Distance from Chicago: 50 miles
• Driving Travel Time: 50 minutes
• Trail Distance: 50 miles
• Hiking Difficulty: Easy to difficult
• Entry Fee: Free for the National Park (except $6 per vehicle fee at West Beach) but note the State Park does have a $7 per car fee with Indiana plates, $12 per car fee with out of state plates
• Pictured above

While northwest Indiana is home to both a National Park and a State Park (and both are worth going to) I’m partial to the National Park which is home to Mount Baldy, the largest ‘living’ sand dune in either park system. 15 miles of southern Lake Michigan is the backdrop to the park and if you don’t want to go for a hike then relax at one of eight beaches.

Starved Rock State Park

• Location: LaSalle County, IL
• Distance from Chicago: 90 miles
• Driving Travel Time: 90 minutes
• Trail Distance: 13 miles
• Hiking Difficulty: Easy to moderate
• Entry Fee: Free

Starved Rock is a beautiful state park not too far from the city. Here you’ll see impressive waterfalls and hike canyons. The time of year to go for the best chance of viewing the waterfall in action is Spring (April showers and such) but since it’s open year-round if you can catch a frozen waterfall that is a sight not many see.

Kettle Moraine State Forest: Southern Unit

• Location: Waukesha County, WI
• Distance from Chicago: 100 miles
• Driving Travel Time: 2 hours
• Trail Distance: Over 100 miles
• Hiking Difficulty: Easy to difficult
• Entry Fee: $8 per car with Wisconsin plates, $11 per car with out of state plates

Sure this is a little further away, but Kettle Moraine is perfect for the novice as well as the experienced hiker. It’s home to one of only 11 National Scenic Trails, the Ice Age Trail follows the edge of the last glacier in Wisconsin. With hiking, camping, and fishing available, there is plenty to keep you entertained in Kettle Moraine. Note there is also a Northern Unit which is larger than the Southern Unit, but it’s farther from Chicago and a little more rural with fewer activities.

Visiting Chicago? Check out these related posts:

• 3-Day Chicago Itinerary for Spring and Summer
• Fall and Winter 3 Day Itinerary
• How to Get Around Downtown Chicago
• The Best Hotels in Chicago
• The Coolest Chicago VRBOs

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

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If short term-rentals are more your thing, check out the coolest VRBO’s in Chicago.

Note: Please confirm with the hotel prior to booking as certain features and amenities may be closed due to global health & safety issues.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Hotels in the West Loop

The West Loop (the neighborhood just west of The Loop) has become the spot for the best restaurants, bars, and nightlife in Chicago. There won’t be a ton of shopping here (go to The Mag Mile for that), and it’s not close to the lake, but if you are looking for the sceniest scene, this is it. It only recently became IT, so there’s still a little grunge (in a good way) on the edges. There are quite a few cool hotels in Chicago located in the West Loop, below are my top three.

Ace Hotel Chicago

I’m a sucker for a good rooftop, and Ace Hotel has a great rooftop restaurant. As a boutique hotel chain, Ace Hotel has an industrial/cool/trendy vibe. Across from Google headquarters, it won’t have the best view from every room, but usually, it’s a great price for a neighborhood that a lot of people want to stay in.

The Hoxton Chicago

Another boutique hotel, The Hoxton Chicago is only one block away from Fulton St. and near a ton of great restaurants. One of the coolest things it has going for it is its outdoor rooftop pool, and if you visit Chicago in the city know there is nothing more luxurious than a pool as an oasis in the city. When you stay at The Hoxton you really feel like you are staying in a hotel in the coolest part of the city.

Nobu Hotel Chicago

It’s no surprise that Nobu Hotel Chicago is right on Randolph Street, aka Restaurant Row. As the West Loop’s 5-star hotel, Nobu has a killer rooftop bar, the highly acclaimed Nobu restaurant, and you’ll feel right at home with the finest in-room amenities from the Dyson hairdryer to the Nespresso machine.

Hotels on the Chicago River

The Chicago River is a unique waterway that connects the Great Lakes to the Mississippi River Basin. Although most of it runs north/south, the main stem runs east/west through the city center. Not only is it cool to see, but Chicago has semi-recently built up the Riverwalk, which is a 1.25-mile pathway right on the river that is sprinkled with restaurants and bars. It’s also a central location, with the Mag Mile to the North and the Loop/Theater District to the south. If you don’t end up staying on the Chicago River, you’ll still definitely want to check it out via an Architectural Boat Tour, trust me.

LondonHouse Chicago

On the south side of the river, LondonHouse is the spot to get amazing river and iconic bridge views. You may or may not get the views from your room, but you most definitely will get the views from their rooftop restaurant and bar.

The Westin Chicago River North

One of the best things about staying in a chain you’re familiar with is you know what you are going to get and this hotel fits the bill. You walk in and it smells just like a Westin, which as a frequent traveler can be comforting! And like most other Westin’s this one is a massive hotel with good service and well-appointed rooms. And since it’s on the river, the possibility of an amazing view too.

The Langham Chicago

The Chicago River’s 5-star hotel is The Langham Chicago. No gimmicks here, just pure luxury with outstanding service, floor-to-ceiling windows in each room, and a 5-star spa.

Related: How to Plan a Vacation (including free timeline planner)

Hotels on the Magnificent Mile & Michigan Ave.

Michigan Avenue is a 12-mile street running north and south through Chicago, and the Magnificent Mile is the northernmost section connecting the Michigan Ave bridge to Oak Street. When you stay on the Magnificent Mile you will be in the heart of shopping, dining, and yes, tourism. If you are a first-time visitor, this will be the most central location to stay. Think, New York Times Square, but add in some charm and remove the stuffed fake Elmo’s.

Four Seasons Hotel Chicago

Located at the northern part of The Mag Mile, the Four Seasons Hotel Chicago is in the 900 North Michigan Ave. building and a stone’s throw to the shops on Oak St. and Oak St. beach, which means one thing, bougie. As a 5-star hotel, the Four Seasons is also one of the top luxury hotels in Chicago with the unrivaled city and lake views and a world-class spa.

Intercontinental Chicago Magnificent Mile

Across the street from The Shops at North Bridge and two blocks to the Chicago River, the Intercontinental is near the end of The Mag Mile (but nowhere near the end of Michigan Ave.) What’s nice is that since it’s just north of the Chicago River it’s only a 15-minute walk to Cloudgate (otherwise known as The Bean). The rooms are fine (aka clean) but finding a hotel in this location, with great city views and is pet-friendly…well that is hard to come by.

Omni Chicago Hotel

Fun fact: when I was younger and Oprah filmed her show in Chicago, during every show they announced that guests of the Oprah Winfrey show stay at the Omni hotel. And that’s what I think of when I think of the Omni. If it’s good enough for Oprah, it’s good enough for me! Located in the middle of The Mag Mile, you will be close to shopping, Oak Street Beach, and the Chicago River.

Historic Chicago Hotels

Chicago is a city full of history (relatively speaking, since the U.S. is a newer country). As one of the largest cities in the U.S., Chicago is by far the largest city in the Midwest and has been an integral part of the nation since 1850. Although much of it was burned to the ground during the Great Chicago Fire of 1871, Chicago rebuilt and has worked to retain much of its rich history. Staying in a place that was built in the 19th or early 20th century has the charm that just can’t be replicated.

Palmer House

Located in the Loop, staying at Palmer House you’ll be right across from the Art Institue and the el will be nearby (note you may hear the train). Palmer House was actually being built during the Great Chicago Fire and had to be rebuilt after it was burned. And rebuild they did. Walking in you can feel the history of hundreds of years gone by.

StayPineapple The Loop

A boutique hotel in The Loop? Who would’ve thought? StayPineapple is a fun hotel in Chicago, but that doesn’t take away that it is in a National Historic Landmark Building. It’s 4 blocks away from Cloudgate and Millenium Park, so it will be easy to have fun inside and outside of the hotel. Oh, and it’s pet friendly, because can a hotel really be fun if your best friend isn’t allowed. Side note: am I the only one who thinks of RHONJ anytime I hear of pineapple lately?

The Drake Hotel

While The Drake may not officially be a 5-star hotel, it feels ever so elegant. Located on the north end of The Mag Mile, The Drake is the quintessential Chicago Hotel. Opening its doors in 1920, 100 years later it still serves high tea in the Palm Court by day and cocktails and dancing at night. If you want to feel the grandeur of Chicago, what it once was and still is, this is it.

Luxury Hotels in Chicago

If you can afford it, why not? Getting pampered in a 5-star hotel makes your vacation complete. Whether you are hitting the town running or taking it a little more low-key, when you get back to your room don’t you just want to feel at home? Or, actually, better than home? It’s a vacation after all.

The Peninsula Chicago

There’s a reason Travel & Leisure ranked The Peninsula as the #1 hotel in Chicago in 2020. With world-class dining and spa options, this is the place to stay. It’s pet-friendly (because even pets deserve to be pampered). Not only is it in a great location along the Mag Mile, but they even offer exclusive outings via The Peninsula Academy.

Waldorf Astoria Chicago

The Waldorf Astoria is located in the Gold Coast, near Rush & Division, by all of the designer shops. It’s only a few blocks from Oak St., Oak St. beach. and Lake Michigan. Built in the style of a French chateau, the Waldorf Astoria is also home to Margeaux Brasserie, where you can get one of the best steak frites in the city.

Park Hyatt Chicago

Situated on Michigan Ave. (technically there is a small park between Michigan Ave. and the hotel), the Park Hyatt is on the Magnificent Mile in front of the historic Chicago Water Tower (one of the few buildings that survived the Great Fire). As you would expect with all 5-star hotels, the service, food, and accommodations are top-notch. An anecdote: as a little girl, I would walk under the Park Hyatt’s heated overhang where guests waited in their fur coats for a taxi, and to me, it just screamed luxury to heat the outdoors. As an adult, I still die for an outdoor heater.

Where the Cool Kids Stay

OK, so this whole post is dedicated to cool Chicago hotels, but in every list, there has to be a ranking. When all you care about is the hotel being v cool, these are for you.

Hotel EMC2

As the name implies, this hotel is all about art and science. From the robot attendants to the restaurant named in honor of Albert Einstein, EMC2 is at the cutting edge of technology (you’ll even have an Amazon Alexa in your room). Located two blocks of The Mag Mile and near Northwestern Hospital (ah, the sounds of the city), it is centralized, but most people stay because it’s just cool.

Viceroy Chicago

A 5-star hotel with an outdoor rooftop pool in Chicago’s Gold Coast? OK so maybe people stay at Viceroy Chicago for reasons other than it’s cool. It’s also luxury with a capital L. So like, cool luxury. Designed in black and gold with floor-to-ceiling windows, the rooms are v cool. Check out the rest of the hotel with the rooftop lounge and if time permits, have them arrange a visit to Aire Ancient Baths to experience a greek and roman style bathhouse, right in Chicago.

Where To Earn or Redeem Hotel Points

In an ideal world, we would stay where we want to stay, regardless of any other factors. The harsh truth is sometimes we want to use points on a trip or sometimes we’re thiiiiiis close to status so we need to book some stays with a chain. When that is the case where are the coolest Chicago hotels to stay that don’t remind you of why you are staying there? Earn your Marriott and Hyatt points at these cool hotels.

Hotel Zachary

You cannot get any closer to Wrigley Field than Marriott’s Hotel Zachary. And because of this phenomenal location, one might think the hotel doesn’t need to be that great. But it is. Paying homage to its location, the hotel is designed in traditional colors and materials but has all the modern conveniences you’d want. And even if you aren’t going to a game, you’ll still get the energy as you look out at the field from your room or the bar. Truly a unique experience.

Chicago Athletic Association

The website doesn’t look like it’s part of Hyatt, but it is. With restaurants like Shake Shack on street level and Cindy’s Rooftop on the top, even locals find the Chicago Athletic Association is a destination. Situated on Michigan Ave right across the street from Millenium Park in a historic building, I like to this of this as a boutique hotel wrapped in the benefits of a chain.

The Gwen

The Gwen is in another historic building (see, Chicago’s rich with history) but is part of Marriott’s The Luxury Collection. Not only is it modern with better than your typical Marriott amenities, but the rooftop restaurant and bar also has gorgeous views of the city. They’ve also introduced the modern tea party, Tipsy Tea at the Gwen offers tea concoctions like ‘High Maintaince’ which is chai spiked with rum. Now, how cool is that?

Thompson Chicago

Part of the Hyatt family, Thomspon Chicago is located in the Gold Coast amongst beautiful homes but very close to the Mag Mile, Oak Street Beach, and Lake Michigan. It might just be the most aesthetically pleasing hotel on the list, furnished in rich velvets and leathers and designed by world-renowned Tara Bernard.

Hotel Lincoln

Hyatt’s Hotel Lincoln, in the Land of Lincoln, across from Lincoln Park…sense a theme? All joking aside, Lincoln Park is Chicago’s largest park and home to the free Lincoln Park Zoo. The hotel is nicely appointed and has an awesome rooftop bar too. Need I say more?

Coming to Chicago? Check out these posts to help with planning.

• The Best of Chicago (what to do, where to go, what to eat)
• 3 Day Chicago Itinerary for the Spring & Summer
• Fall & Winter 3 Day Chicago Itinerary

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Before you travel, make sure your toiletry bag is stacked!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

The post Coolest Hotels in Chicago appeared first on Very Obsessed.

Short-term rentals have become very popular in recent years, with sites like Airbnb and VRBO dominating the scene. The two sites have a few differences but are mostly similar in that they are phone-app based, feature a large selection of accommodations, and offer multiple filters to hone in on exactly what you are looking for. While Airbnb technically has more inventory, because VRBO only rents entire spaces (no single rooms like Airbnb) I prefer to start my search there. VRBO also lets you filter on some advanced features, like private pool, that Airbnb doesn’t.

One, if not the, most important things to look at when deciding where to stay is location, location, location. Especially in a city like Chicago that has a wide range of neighborhoods (downtown or trendy?) and features (by the water or the train?) you don’t want to be disappointed by where you are staying. Luckily, I’ve done the research for you, and here are some awesome VRBO options in Chicago.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Sleeps 8

Single Family Mansion

Want to stay in what I assume is a multi-million dollar home in Chicago? This is it. This beautiful single-family home with a garage is in the most prestigious part of the city. 4 bedrooms, 5 bathrooms so although it will cost you, would be a gorgeous place to stay for a multi-family vacation or a group of friends. I mean there’s a legit wood-burning fireplace in the bathroom. I’m pretty sure this bathroom is bigger than the blue banana. There is a private outdoor space although since it’s a single-family home surrounded by high rises it doesn’t really have that much privacy.

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Sleeps 8

Penthouses Don’t Come on the First Floor

Pricy? Yes. But these are million-dollar views in this penthouse we’re talking about. And a huge private outdoor space. The living room takes up two full stories so with the wall of glass you can see quintessential Chicago landmarks… the Handcock, the shops at 900 N Michigan Ave, Lake Michigan. It’s a stunning apartment. The unit also has access to the outdoor pool, which isn’t super common in the city, if you are here in the summer and a pool is more your vibe than the beach. Although don’t discount Chicago beaches

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Sleeps 5

Great for Shopping

This apartment feels like a boutique hotel room. With floor-to-ceiling windows and a private balcony, this is a sweet 2 bedroom. Situated between Oak Street and Magnificent Mile, there is an abundance of shopping options to choose from.

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Sleeps 4

Entertainer’s Delight

This single-family home is technically in Old Town, which is north of downtown, but it’s close to Second City, 3 Arts Club Cafe, and a ton to do. Not only is this not your typical high-rise vibe, but the chandelier in the dining room also screams glamour. The owners will connect you with a private chef or baker in case you also want to have a dinner party or celebrate a birthday. How cool is that?

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Sleeps 5

River Views

With an outdoor pool, this apartment is in the heart of the city. Here you can take advantage of both the Chicago River and architecturally rich skyline views. Since it’s right by the Merchandise Mart you may hear the train, but on the bright side you’ll be very close to the world-class el system.

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Sleeps 8

Views for Days

This penthouse features awesome views of Lake Michigan, the Chicago River, and Navy Pier. The inside is nicely furnished but it’s all about the views and the location. And reasonably priced for bedrooms in the city, it would be hard to find that at a hotel.

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Sleeps 6

City Living

This 2 bedroom apartment may be basic but it has everything you need to feel like you are living the city life. Floor to ceiling windows, a private balcony, and an outdoor pool in the center of the city.

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Coming to Chicago? Check out these posts before you come.

• The Best of Chicago (what to do, where to go, what to eat)
• 3 Day Chicago Itinerary for the Spring & Summer
• 23 Cool Hotels in Chicago
• Fall and Winter 3 Day Chicago Itinerary

Before you travel, make sure your toiletry bag is stacked!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

The post Cool Downtown Chicago VRBO Rentals appeared first on Very Obsessed.

In my 20’s I moved to the city (Wrigleyville, Go Cubs!) to attend college and came back in my 30’s as a sort of homecoming.  For those of you who haven’t been, Chicago is centrally located in the nation and has two major airports so it’s a perfect choice for a long weekend trip.  How to Get Around Downtown Chicago has great tips on the public transportation system, one of the best in the country.

Chicago is home to four distinct seasons so depending on when you visit you can have totally different experiences.  There is so much to do, but here are a few of my favorites:

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Where to Stay

There are different reasons to choose where to stay, usually, it depends on what type of trip I’m planning and looking to spend.  In Chicago, I recommend a hotel with a great location.

• The Drake | This hotel screams quintessential Chicago.  Sitting right off Michigan Ave (aka Magnificent Mile), it’s close to luxury shopping in the Oak Street District and a 10-minute walk to Oak Street Beach.  Fun fact, it was the first place I ever had a proper afternoon tea.  Oh, and it’s now part of the Hilton Hotel family so you can earn some points.
• Hotel Zachary | For something totally different, this hotel is right outside of Wrigley Field, home to the Cubs.  If you are planning on seeing a game, there’s nothing like being close to the action.  Even though it’s in a neighborhood, it’s really walkable and two blocks away from the Red Line on the L.  This is a Marriott Tribute Portfolio property so points a plus!
• The Hoxton | Steps away from Chicago’s Randolph Restaurant Row, staying at the Hoxton you will have an endless selection of places to dine.  The West Loop has become a popular spot in Chicago filled with trendy restaurants and shopping.

Where to Caffeinate

What makes a good coffeehouse to me is a place that has a good vibe, good coffee, and good food; the trifecta for me to go back. If not all 3 are in place, it’s not on my list.

• Big Shoulders Coffee | Cool coffeehouse vibe but not too cool that they don’t have specialty drinks. I love the marshmallow latte and I hear the breakfast sandwich is pretty solid. 

• Dark Matter Coffee | Dark Matter has 8 spots around the city and it’s where the locals go. Not only do they produce their own coffee, they are transparent in the entire process (check out their site for all the deets). Their forte is coffee but I love that they partner with local bakeries and restarants around town to offer great food as well. My favorite spot is The Mothership in Ukranian Village. They offer donuts from Do-Rite, pastries from West Town Bakery and breakfast tacos from Cafe Tola.

• Goddess and the Baker | While they don’t brew their own coffee, Goddess has amazing coffee and tea drinks and you can’t beat them for their bakery section. 

Where to Brunch

I prefer this over lunch, you can get something savory or sweet and day drinking is encouraged. I love brunch so much I have a whole post on Where to Brunch in Chicago.

• Beatrix | With serveral locations around the city, I love the Fulton Market spot with it’s large outdoor patio. It doesn’t matter if you are looking for something sweet or savory, healthy or not, this spot has you covered.

• The Hampton Social | Relaxed and upscale, all at the same time, kind of like the Hamptons. The food is very good and perfect for a long leisurely meal with plenty of morning cocktails.

• Paradise Park | Located in the Wicker Park neighborhood, this pizza spot is the place to go for a little hair of the dog, or just some day drinking. They have a great roof where you sit in lawn chairs and the cocktails are fun! 

Related: Best of Milwaukee

The Dinner Scene

One of life’s simple pleasures is a long leisurely meal with wonderful company and great conversation. 

• Maple & Ash | This is a place to go when you are celebrating a special occasion. The food is fantastic (Steakhouse but many other options) and the vibe is a scene (in the very best way). They start you off with a complimentary cocktail served in a champagne saucer, I think you get the vibe. I could go on and on but come with a hearty appetite and be prepared to get those credit card points because this one will cost you.  

• Small Cheval | The burger at Au Cheval was named best in America by the daily meal.  While Au Cheval has many tasty items on the menu it also generally comes with a long wait (I’m talking about 2 hours long). Although they claim it’s different, to me the burger at Small Cheval is just as good. It’s the fast-casual spin-off with a much more reasonable wait time and outdoor patio in good weather.  I highly recommend a single-stack cheeseburger, fries, and a vanilla shake with a shot of amaretto. Nothing else like it. 

• Lou Malnati’s | While some may scoff that this has become a “chain”, it’s expanded for a reason. It’s delicious, it’s unique, and it’s pizza.  There are a lot of deep-dish places to try in Chicago, but in my opinion, Lou’s is the best. So much so that I’ve had it shipped to me while I lived in different states across the country. Oh, and if you aren’t a fan of deep dish they make an excellent salad and their thin crust has a decadent quality too. 

When You Want to Play Outside

Chicago is a beautiful city known for its architecture and has four distinct seasons.

• Catch a Game(Bears/Cubs) | Depending on the month, you can almost always find a game to go to.  While Chicago teams may not win all the time, they have a loyal fan base and will probably be sold out (hello StubHub).  Be warned, Chicagoans play in the elements so be prepared for anything. 

• Walk the Lake Shore | Chicago is known for their expansive waterfront right on Lake Michigan. Those who haven’t seen a Great Lake…it’s like an ocean, with no sharks. The Chicago Lakefront Trail is over 18 miles long so you can access it from any direction. There are restaurants and museums and usable beaches which means you can easily spend all day exploring. 

• Lincoln Park Zoo | A zoo that is open 365 days a year AND is free?  That’s right, LPZ has a wide range of animals and hosts events all year long, rain or shine. During winter months they host ZooLights at night which cannot be missed; bundle up, grab a holiday drink and try to spot the animals (who are probably hiding because they are trying to sleep but that’s part of the charm).

When You Want to Stay Inside

When you don’t want to necessarily experience all of those four seasons…

• Magic Lounge | A hidden gem in the city.  You enter through a fake laundromat but once inside you are transported to another era.  There’s a bar where you can chill and watch close-up magic or buy tickets to the show and be entertained. Magicians come to your table before the main event and each time I’m blown away that I can’t figure out the trick. 

• Second City | World-renowned for their improv, Second City has a couple of theaters with a variety of shows. Many A-List performers got their start here so the talent speaks for itself. They’ve also opened a rooftop bar although I haven’t been yet. 

• Field Museum | Chicago has a wide selection of world-class museums.  The Field Museum is home to the largest T-Rex but I’m partial to the Grainger Hall of Gems

Sweat Sesh

WheYoga is my jam, so by sweat…I mean yoga. n you don’t want to necessarily experience all of those four seasons…

• Lululemon | The experiential location on North and Clybourn has two exercise studios, a meditation space and a cafe. Two of my favorite yoga teachers in the city teach here. It’s a luxury studio meaning you don’t need to bring any equipment (leave your mat at home) and they have Dyson blow dryers in the locker room, doesn’t get any better than that. 

• Ritual Hot Yoga | A unique experience, they teach in a very stylized manner.  The rooms are dark, lit by candlelight and very hot. You may be overwhelmed in the first class, but you will get the hang of it and know you got in a killer workout.

• CorePower Yoga | A chain, I know I know, but it’s solid. You know what you are going to get and there’s one in what seems like every neighborhood, quite accessible. 

Take the planning out of your next Chicago trip and check out the 3 Day Itinerary for Spring & Summer. 

Still looking for places to stay? Here’s a list of the coolest hotels and VRBOs in Chicago.

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

The post Best of Chicago appeared first on Very Obsessed.

A perfect trip to me has a balance between seeing the sights and leaving time to explore. If you are looking for a quick list of the best Chicago has to offer, check out my Best of Chicago guide.

If you buy something through my links, I may earn a small commission at no additional cost to you. I appreciate your support! See disclosure for details.

Day One | Today is about really seeing the city.

Day

A great place to start the trip on a beautiful warm day is Cindy’s Rooftop.  Right on Michigan Avenue, you’ll be able to see Lake Michigan, Millenium Park, and the famous “Chicago Bean”.  Depending on the day of the week you’ll have lunch or brunch (only served on weekends). If you are the type of person that needs sustenance upon waking (I myself need coffee) then grab some coffee and a pastry from whatever local shop is near and then plan to go to Cindy’s for small bites.  The view is not to be missed.

After you’ve seen the city from 13 stories high, walk over to Navy Pier and take an Architectural Boat Tour to see the city from the water.  You’ll learn a lot about the city and gain a whole new appreciation for the architecture in Chicago after the tour. Also, for a city that is known for the lake, river, and bridges, it would be a shame not to experience it first hand.  There are a few tours but I recommend Shoreline, I’ve always had great experiences with the guides which I’ve found can make or break the experience.

Once the tour has finished and you disembark at Navy Pier, take a bit of time to explore.  Yes, it’s very touristy, but you are a tourist after all! Navy Pier is home to the Centennial Ferris Wheel and it’s another chance to see Chicago from a different view.  After Navy Pier, you can continue walking the lakeshore on the Chicago Lakefront Trail for yet another view.  I would recommend walking south and then you can go to the Bean, Buckingham Fountain, and Grant Park.

I have a whole Chicago Brunch Guide if you are looking for other options.

Night

If time allows (which this should) I like to take some time to go back to the hotel and freshen up before dinner.  Tonight’s spot is Maple & Ash for some of the best food in the city. It’s a scene so take the opportunity to get changed, throw on some heels, and take a Lyft to dinner.  If you get there a little early, you can grab a spot at the bar and have a pre-dinner cocktail because those are delicious and it’s a great spot for people-watching.

You can call it a night, or have a nightcap back at your hotel.  A lot of Chicago hotels have rooftop bars so if you are lucky enough to be staying in one of those, do take advantage sometime during your trip. 

Related: My favorite travel beauty items and toiletries

Day Two | Enjoy the city like a local!

Day

After the jam-packed day yesterday, this morning starts with a laid-back brunch at The Hampton Social.  There are two locations for The Hampton Social but I recommend the Streeterville location for this itinerary since there is a rooftop and it’s closer to our next stop. Ask for a table on the rooftop but if you can’t get that then a table next to the windows will also give you some fresh air.  

After brunch, we are going to the beach!  I like to stop and get beverages and maybe some snacks (why does the sun make you so hungry?) and there is a Whole Foods on the way there.  It is about a 15 minutes walk from The Hampton Social to Ohio Street Beach. Whole Foods is a block east of The Hampton Social on your way there on Grand Ave.  Chicago has a lot of beaches on Lake Michigan but I’ve chosen Ohio Street due to its close proximity. Feel free to venture up north and go to the more populated Oak Street or North Avenue beaches.

If your hotel is anywhere near this location then I would take the time now to freshen up before dinner.  If it’s more north then you can freshen up after the next stop…

Night

The Zoo!!!  Chicago is awesome because it has a FREE zoo right in the city that is open 365 days a year.  Yes, Lincoln Park Zoo really is somewhere locals go. There are CTA buses that take you right there or you can rent a Divvy Bike if that’s something that interests you (I’ve never been particularly fond of riding a bike in the city).  The zoo closes at 6:30 on weekends so make sure to plan accordingly. But hey, it’s free so even seeing a little of it is totally worth it!

From Lincoln Park, walk the 20 minutes to Small Cheval on Wells St.  You can’t go wrong with anything here, but if you’d like to see my exact order check out my Best of Chicago guide.  Place your order and then grab a seat at the picnic-style tables.

After you’ve had your amaretto shake it’s a 10-minute walk to The Second City to get your laugh on.  Improv is one of the things Chicago is known for and there are different shows depending on what you are looking for.  If you have time before or after the show head to Utopian Tailgate which is a casual rooftop bar on top of The Second City.

Related: Unexpected travel essentials to take on your next trip

Related: What to do in Milwaukee ( a quick trip from Chicago)

Day Three | Becoming a fan

Day

Head over to Goddess and the Baker for breakfast this morning.  They have delicious coffee drinks and then you can choose something savory or something sweet to eat (or both!).  Today’s Chicago itinerary is classic day drinking. If you do choose to imbibe, I would definitely recommend using this to lay down a base.  

Hop on the CTA Red Line to Wrigley Field, home of the Chicago Cubs MLB team.  Public transportation can seem a bit daunting if you don’t know what to do, but I promise Chicago is an easy city to navigate.  For the full rundown check out my tips for How to Get Around Downtown Chicago. You’ll get off on the Addison stop for Wrigley Field.  There are probably going to be a lot of other people on the train in full-blown Cubs gear so follow their lead.

Wrigley Field and the surrounding area have been built up in recent years.  To get into the spirit (and spirits, haha) head to a bar and have some pre-game cocktails.  Depending on what you are looking for there are the classic dive bars like Murphy’s Bleachers or something more elevated like Mordecai.  Wrigleyville does have something for every kind of baseball fan.  

Night

Once the game is over there will be a lot, I do mean a lot of people leaving the stadium.  You can either start your walk to dinner now or wait until the crowd dies down at one of the bars or restaurants around the Field.

Dinner will be at Lou Malnati’s which is a 30 minute walk from Wrigley Field.  While they do have an exceptional thin crust here, can you really come to Chicago without trying the deep dish?  The answer is no, no you cannot. So do yourself a favor and try the deep dish with a butter crust. If you are craving some produce in your life after what has been a long, indulgent day, the Malnati Salad is so good.

Day drinking always makes me tired so I would call it an early night, knowing tomorrow is a travel day.

My Kind of Town, Chicago Is

I hope this has been a good starting point for your Chicago itinerary.   This is by no means exhaustive…if you live near an awesome beach, don’t spend your time in Chicago doing that, go to a museum instead. But if you live in a landlocked area, take advantage as not everyone thinks of Chicago as a beach city.  If you want a snack, hit up Garrett’s Popcorn or Molly’s Cupcake and you won’t be disappointed.  Oh, and check the weather and the sports schedule to see if you need to make any adjustments.  

Check out these other travel posts!

DISCLOSURE: If you buy something through my links, I may earn an affiliate commission, at no cost to you. I only feature products I would use myself, and all opinions expressed here are my own. I am very obsessed with FTC compliance so check out my full disclosure for details.

Pin this to save for later!  

The post 3 Day Chicago Itinerary for Spring & Summer appeared first on Very Obsessed.

Getting to Chicago

There are three major ways to get to Chicago.  You can fly, take a train or drive depending on how far you are located and what your plans are.

Planes

If you are over a 4 hour’s drive away I would recommend flying but that’s totally your preference.  

Chicago has two airports, Chicago O’hare and Chicago Midway.  O’hare is a huge airport northwest of downtown while Midway is southwest of downtown and a little easier to navigate.  Both airports have a CTA train directly inside that can take you downtown (more on that below) which I recommend.

Trains

If you are closer than 4 hours and are near a train station I recommend taking a train.  

I really enjoy train travel if the stations are convenient.  Unlike airports, you don’t have to get to the station really early and deal with pre-boarding but you still get the benefit of being able to do whatever you want on your journey.  The trains that will take you into downtown Chicago are Amtrak (long distance), Metra (Illinois/Wisconsin commuter), and the South Shore Line (Indiana commuter).

• Amtrak will take you into Union Station which is located just outside of the Chicago Loop (a commercial area located downtown).  Since it’s outside of the loop it’s kind of in an odd area to be walking around with a suitcase which is why I recommend taking a Lyft to your hotel.
• Metra has multiple stops depending on where in the city your final destination is and where you are originating from, best to check the Metra website for more details. The two stops that are outside of the loop are Ogilvie Transportation Center and Union Station which are about a 5 minute walk apart.  If either of these is your stop then again, I’d recommend taking a Lyft. If you are getting off inside the loop then you have multiple options depending on where your hotel is located.
• The South Shore Line ends at Millenium Station located inside of the Chicago Loop on Michigan Ave and Randolph St. This location is pretty accessible to anywhere you’d like to go in the city.

Automobiles

If you are close-ish and plan on trekking out to the suburbs you may want to drive.

Parking is a hassle in Chicago and in many areas it’s also expensive. I don’t recommend taking a car unless you know you’ll have an inexpensive, easily accessible spot, in which case, congratulations!  With so many transportation options available driving is something I’d rather not worry about, but you do you.

You can also get to Chicago by bus but to be honest I’d rather take a train if I’m close enough that I’m not going to fly. 

Getting Around Chicago

There are 4 main ways to get around downtown Chicago. You can take the “L” or “El” (spelled both ways but pronounced like the letter) train, bus, Lyft, or drive.

CTA L 

I’ve lived in Chicago and New York and I have to say, the L is so much easier to navigate than the subway. If you’ve ever taken the subway then this will be a piece of cake.  It’s nicknamed the L because of the Elevated tracks but just like the subway, there are parts that are elevated and parts that go underground.

To get on the L you’ll need to either use a Ventra card (which can be purchased at a Kiosk) or you can use a contactless credit card at the turnstile.  Most rides will cost $2.50 per ride and there are unlimited passes you can purchase as well. The lines are set up by color and are identified by the first and last stop on the route. There are 8 color lines and they all go downtown.  Usually, the L can be an inexpensive and efficient way to get around. The train’s ETA is updated on Google maps so you can see when the next one will arrive or how long you need to wait.

I mentioned above that the L goes directly into both airports.  The blue line goes into O’hare and the orange line goes into Midway.  Going to the airport the train will say O’hare or Midway, leaving the airport it will say Forest Park or Downtown for you to get into the city.  Taking the train downtown is really common so you should feel totally comfortable doing this. 

CTA Bus

CTA operates a lot of buses on a variety of routes. 

I recommend typing your destination into Google maps and it will tell you which bus numbers you can take. Then walk to the bus stop and wait for it to arrive.  The CTA buses also take the Ventra cards I mentioned above or contactless credit cards. There aren’t Ventra kiosks at the bus stop though so if you don’t already have a card then you’ll have to use contactless or find an L stop to buy a card.  

Sometimes the best way to get across town is a bus as there aren’t many cross-town L’s (especially north or south of the loop).  I’ve found that when I’m on the bus it always takes longer than Google says it’s going to take though because just like cars, the buses have to battle traffic.

Lyft

Sometimes you just don’t want to deal with public transportation and that’s OK.  I recommend Lyft.  

Maybe you’re wearing heels, maybe it’s late and you don’t want to wait 15 minutes for the train or maybe there isn’t a convenient stop…it really doesn’t matter the reason for not wanting to take public transportation.  Luckily Chicago is pretty accommodating to Lyft and you can hail one at either airport (although that can get pretty pricey) and they are plentiful downtown.

Taxi’s are available in Chicago but I’ve found when I’ve taken them recently that the drivers aren’t any more knowledgeable than Lyft drivers (which used to be a benefit).  I also prefer not to have to talk to the drivers to tell them where I’m going and also figuring out the whole payment thing is a pain.

Car

If you’ve decided to drive to Chicago then you are probably planning on driving around Chicago as well.  

There is some street parking and you might be lucky enough to find it.  Most downtown is metered and while you can pay the meter like back in the day there is also an app for the phone called ParkChicago.  I highly recommend getting this and setting it up before you try to park. It’s easy to pay for your parking on the app and if you are out and about you’ll get a notification when the time is expiring and you can extend your time.  Parking tickets in Chicago are no joke, I’ve let my time expire by 5 minutes before and gotten a $50 ticket.  

Certain streets are permitted parking only during certain times (usually overnight into the morning) so if you want to park there a resident will have to give you a daily pass.  They are inexpensive but don’t let that fool you, if you don’t have one don’t be surprised to wake up with a city parking ticket.

If there is no street parking then there are several garages to choose from but they can get expensive which is why I don’t generally recommend it.  If you are going that route then I like to use the SpotHero app to find a good deal and prepay.

Now that you know how to get around, check out these other Chicago guides:

• Best Hikes Near Chicago
• Coolest Chicago Hotels
• Where to VRBO in Chicago
• 3 Day Chicago Itinerary for Spring & Summer

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