Best of Chicago

Growing up an hour outside Chicago, this was the first major city I felt a connection with.

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:

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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! 

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Related: Best of Milwaukee

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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.

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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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