2 Days in Chicago: A First-Time Itinerary
I grew up in the Chicago suburbs, but have lived in the city on and off for over five years. I love to share my Windy City recommendations, and I have a ton! Below is the perfect itinerary for how to spend 2 days in Chicago for your first time visiting. Have fun!!!
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Table of Contents
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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One Comment
Sonia
This is super helpful. I’m pinning it for my trip to Chicago in May.