Chicago is one of the US’s biggest cities, and a large travel destination for business and pleasure. So, where do you start with such a HUGE city to conquer? Here’s our Chicago Travel Guide: our top picks for the touristy Windy City adventure everyone NEEDS to have. This is an ongoing and changing guide, so please comment with your FAVORITE things to do (especially for first-time visitors) in the Windy City.
(Note that I’ve organized the days in order of what you should do. Willis Tower is definitely a morning thing, while a sunset Architecture Tour is the perfect time to cruise the river!)
Willis Tower is a pretty iconic destination for many reasons … all of which make it difficult to get to the top without spending hours. Be sure to get there right when it opens, and definitely on a weekday if you can. Also, if you are scared of heights, claustrophobic, or a deadly combo of the two, DO NOT ATTEMPT.
(2 hours, if you make it there on time)
Lincoln Park Zoo is a MUST-SEE item and not simply because it’s an awesome free zoo. There’s a quaint park (one of several the good people of Chicago voted to keep protected from all building permissions so it will be green forever) right outside the zoo with one of the most beautiful conservatories I’ve ever seen. It’s also really close to Oz Park (if you’d like to see some Wizard of Oz statues) and really close to Floriole (lunch and dessert) and Mandy B’s (more dessert). If you do the Zoo and Conservatory before, then Oz Park, then lunch at Floriole and Mandy B’s, you might have a pretty good day.
I won’t tell you more than once. Or fifteen times. GO TO FLORIOLE. Not only is it in a beautiful spot, but the pastries and food there are incredible. You’ve got to go! Eat lunch and get multiple pastries. I don’t care if you’re past liking food after lunch and a couple pastries. Just do it.
Sweet Mandy B’s
Looking for more dessert following dessert? Don’t skip Mandy B’s. PRO TIP. Get some pastries. Sneak said baked goods into iO Theatre. Eat sneakily while watching show. Leave crumbs as your criminal calling card. Feel like Al Capone.
iO Theatre (or Second City)
Let’s say this upfront: I was pretty skeptical about iO. I’m decently skeptical about improv in general, so nothing against this theatre, ESPECIALLY because it’s one of the best in the country. Michael did the research on this one, so he knew I would like it, but anyway. He chose the Improvised Shakespeare Company show (most nights at 8 PM) and I kid you not: FUNNIEST THING IN THE WORLD. We were laughing from beginning to end. We quoted it for days after. I wished that we had more time in Chicago to see another show because it was so good. So just go.
Second City is also supposed to be amazing (what Hogwarts is to Harry, Second City is to Bill Murray, Tina Fey, and Amy Poehler and more) so just go to that too if you have the chance! (A little pricier and racier.)
Guys. I know this is a dessert-filled day. But finish your night like a SUGAR PRO ON THE WAY TO THE DIABETIC SUPER BOWL and go to Jeni’s. Once you go once, you’ll go every night. But don’t worry, I’ve penciled that in for you. You’re welcome.
The Art Institute of Chicago is reeeeally cool. And not simply because you can recreate a large and iconic portion of Ferris Bueller (side note: if you ever wanted any Ferris Bueller swag, Chicago is the place to get it). With Van Gogh’s The bedroom, Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, Nighthawks by Edward Cooper, and Picasso’s The Old Guitarist, plus a few beautiful Monet paintings, you’ll be pleasantly surprised.
While you are at the Art Institute, walk down to The Bean. It’s, you know, a little iconic and typical for a Chicago travel guide. It is swarming with people so beware.
(2 to 4 hours)
I’m not joking when I say this. BEST BURGER EVER. However, there is a caveat. We waited for almost 2 hours before we got seated, and we arrived there at the all hallowed hour of 3PM, where the universe has always agreed that most restaurants are empty. PLAN ACCORDINGLY. With no reservations, and a long wait at any time of the day, we recommend setting aside a few hours for this treat and going during the day. There’s also a really fun indoor market (French Market) that we explored while waiting, and it’s just down the street. You can also stop in at Little Goat for some baked goods or a drink, which is just down the street too! Foodie heaven street, am I right?
The Architecture River Tour (go with CAF, they have the best tours, even though they are pricier) is one of the coolest things to do in Chicago, especially if you aren’t familiar with the city at all. The tour guide explains each building in detail, noting the time period in which it was built, what it was originally used for, and what it was modeled after, with tons of interesting stories about the city, the people, and how Chicago grew to be the huge city it is today.
PRO TIP: Choose the later evening tour so that you can take photos of Chicago at sunset. Worth it.
I wasn’t sure how much I would love deep-dish pizza, and even though deep dish pizza is a controversial topic in Chicago (Chicagoans think it’s mostly for the tourists, but every Chicagoan has an opinion on it, and tourists are convinced that Chicagoans eat this ere’day), it’s worth trying. Though there are lots of places to get it, I loved Bella Bacino’s spinach and mushroom packed deep dish pizza, but you’ll hear Gino’s and Lou Malnati’s recommended by at least every other person (and Lou Malnati’s in Chicagese will sound like Illuminati and you might jump out of your Uber at the next stoplight). It was incredibly delicious, the wait was almost nothing, and look at that cheese. YES. A Chicago travel guide must.
Just do it.
The Museum of Science and Industry was another really awesome museum that we loved. With so many interesting exhibits, (my favorite was Extreme Ice and Science Storms) we could have spent hours there! It’s the perfect spot to entertain kids and adults for hours while learning a ton about the world.
Pastoral is a great spot if you are looking for a quick sandwich, but they also have a ton of fun cheeses to try and some local food products like jams, jellies, and the like. The employees are incredibly cheducated (like cheddar educated, but other cheeses too…they just know so much about cheese). Really good sandwiches and be sure to get anything with tomato jam on it.
Though we didn’t get to experience this tour (we were there a week too early!!) we have it on our list of things to do next time we are in Chicago. If you can go, do it!
Fonda Frontera (our choice) was an awesome surprise for us. Anything you get there is awesome, but be sure to get the chips (a thicker corn chip that’s surprisingly delicious) and the churros. SO good.
You know the drill.
Where to Stay:
We love staying in Airbnb when we travel, and Chicago was no exception. We stayed in the Wicker Park/Ukrainian Village area and thought it was the perfect spot. Our Airbnb hosts were AWESOME and we honestly had the best time chatting with them. Thanks to Mark and Daniela!
Side note: This trip was planned with so many recommendations, but Alex Steele was super helpful in providing some of the best recommendations for any trip I’ve ever taken. Check out her awesome photography. And please comment to add YOUR addition to our Chicago Travel Guide.