Chicago is such an amazing city! I got to go there last year for the first time, and while our main reason for going was to see Hamilton (work! work!), I actually really fell in love with the city and all things to do in Chicago!
From taking a river tour to eating fantastic food, there are all kinds of sights to see and things that will make your trip to unforgettable. Here are our top 5 things to do in Chicago!
Take the Chicago Architecture Boat Tour
Taking the boat tour with the Chicago Architecture Center was one of our most memorable experiences in Chicago.
When you are in Chicago you will see tons of boats taking tourists up and down the Chicago River, so you want to make sure you get the RIGHT cruise. As in, the one that isn’t going to just take your money and put you on a boat with a bunch of people to look at the pretty buildings. You want the one that is going to take your money and put you on a boat with a bunch of people to look at the pretty buildings with a trained Chicago Architecture Center docent.
I know, I know, it might sound a bit dry to you. Like, do I really want to listen to someone talk about architecture for 90 minutes on a boat?
But I can promise you, YES, yes you do. Not only will your guide explain to you the architectural periods of the buildings and point out the engineering feats along the Chicago River, you’ll also get a crash course in the history of Chicago which is actually very interesting! AND you’ll get stunning views of Chicago the whole way!
Honestly, if you are going to do one thing in Chicago, the Chicago Architecture Center boat tour should be it!
Check out their website for prices, times, and other details.
Eat Some Fantastic Food
Chicago has no shortage of fantastic restaurants. Obviously, you have to eat some deep dish pizza while you are there. This is, of course, something you can find all over the place. We opted for Giordano’s, a local chain a local recommended to us, and I can’t say we were disappointed. (Be prepared for lines though. You can order it to go if needed.)
But Chicago also has a ton of other great restaurants, too. We loved our dinner at Quartino Ristorante, an Italian restaurant known for their small plates.
We also had one of the best breakfasts we’ve had in years at Little Goat Diner.
A few more restaurants to check out (these were on our well-researched list to try, but we just couldn’t make it to all of them on a short trip):
Girl & the Goat
Au Cheval (apparently the best burgers ever)
Stroll Through the Parks (and Don’t Forget The Bean!)
Taking your picture in the reflection of The Bean (aka Cloud Gate) might be one of the top things to do in Chicago, or at least the top according to Instagram feeds everywhere. It’s a fun thing to do though and it won’t take too much of your time! So definitely make a point to stop by.
But there are other things to explore in Chicago’s parks too. We really enjoyed our strolls through Millennium Park (where Cloud Gate is) and Maggie Daley Park (they are right next door to each other). Plus don’t forget to stop by Buckingham Fountain in Grant Park.
See Chicago City Views
Another top thing to do in Chicago is to see a view of the city from above. There are lots of ways to do this, like buying tickets to go up to The Skydeck at Willis Tower (where you can step out onto the glass ledge if you are brave enough!) or the 360 CHICAGO Observation Deck.
But our favorite way to see the Chicago city views can come with just the price of the a couple of cocktails: The Signature Lounge at the 96th. This lounge is a cocktail bar attached to the Signature Room at the 95th. Just take the elevator up, get in the line, and the host will give you a table. It is becoming more popular so be prepared for a wait though.
The seats at the front will almost always be taken, so if you’d like to be able to move tables once someone vacates, let the servers know and they can move you up when someone else leaves (they usually have a waitlist going though, so don’t assume someone getting up means the table is free to take).
Also, girls: go to the bathroom while you are there! This sounds like a weird thing to say, but the women’s restroom has the best view of the entire place! (Sorry guys…no view for you.)
Visit Chicago’s Museums
Chicago has so many museums to choose from! Honestly, we haven’t been able to make it to a museum in Chicago yet, but I’m dying to go to the Art Institute (I really want to see the Thorne Miniature Rooms).
So there you have it: our top 5 things to do in Chicago! Honestly I wasn’t sure about the city before we went (let’s be honest, our main focus was Hamilton), but I really loved the city and now I want to find an excuse to go back!