10 Fun and Cheap Things to do in Chicago

Chicago can get pretty pricey (all downtown hotels were like $500 a night the weekend we were going!!!), but there are tons of budget-friendly options for your Chicago bucket list. Here are some fun and cheap things to do in Chicago.

Everything on this list is $15 or under and I give you the details on what you’ll spend at each. Chicago is one of the most visited cities in the US and I am so glad I got to visit again this last spring!

1. Grab a drink with a view


There are a few options of observation decks in Chicago like the glass floor at at the Chicago SkyDeck, but it costs over $25 just to visit + $10 for the glass leaning experience. I actually ended up seeing the Signature Room at Willis Tower on someone’s Instagram story and knew I had to visit! It’s free to enter this beautiful bar, but the price of a cocktail is more. I got a non-alcoholic drink for $8 though.

The Signature Lounge is just two floors down (96th floor) from the observation deck above. We loved sitting and sipping our drinks though overlooking the entire city of Chicago though instead of wading through tourists. It was beautiful and the fact that a drink was included was worth it.

2. Ride Divvy Bikes

$2 per ride, $15 for the day

Divvy Bike is Chicago’s bike share program. You can rent one of their bikes from any station around the city (there are tons!) and ride from spot to spot. A single ride is $2 or rent for the day for $15 so because we were planning to ride several times, we chose to rent for the whole day giving us freedom to bike everywhere we wanted to go.

We rode along the lake and were able to take in some awesome views. Highly recommend!

3. River Walk


Chicago is built along a river and the views are just gorgeous! Walk along the water and across bridges for great views (there are many). City Winery has a great spot on the water with tables and delicious wine to take in the views. A drink there will cost you about $10 and it’s worth sitting and sipping with the view.
4. Magnificent Mile


Shopping this area is not free of course! But window shopping definitely is. We chose to ride bikes along the Magnificent Mile to take it in, but you can walk it as well and window shop. It’s Chicago’s most famous street and worth the visit! 

This area is also known as one of the best areas to stay in Chicago because of it’s proximity to activities, public transit, and shopping!


5. Millennium Park

Millennium Park is large and beautiful. We loved walking around and seeing all the beautiful views of the city from inside the park. “The Bean” is the most famous piece of art in the park and worth the stop! At 10 am it was already extremely packed but we did get to snap a good selfie and walk through.

You can play mini-golf right in Millenium Park for just $8 a person and it looks like so much fun! The views while you play are great. You can find the mini-golf course over the bridge in the children’s section of the park next to the playgrounds.

6. Navy Pier

free to $15

Navy Pier is home to the Children’s Museum, boat tours, lots of restaurants, shops, and rides. There’s tons to choose from but the Ferris wheel is probably my favorite ride. I first road the Ferris wheel at Navy Pier when I was 9 and so riding it again was so special! Plus since it was invented there, you feel like you are a part of the history! The views were gorgeous which is definitely an added bonus (and I’m all about a good view!).

Each ride is about $8 – $15 with the Ferris Wheel costing the most.

Fun fact – did you know the Ferris Wheel was invented in Chicago? They created it for the World’s Fair in 1883. At first they considered creating a larger version of the Eiffel Tower, but as Americans do… they wanted to be different! So a guy named George Ferris came up with the idea of a giant spinning wheel people could ride on. The original Ferris Wheel was not at Navy Pier but it is cool to ride one where the Ferris Wheel was invented.

You can also grab a drink from one of the bars along the pier and carry it around with you anywhere you go which is awesome. Highly recommend doing this!

7. Goose Island Brewery Tour

$10 -$15
Goose Island is located right in Chicago and while available nationally, it’s fun to visit the home of the beer and try out their local only beers. You can do a tasting for $10-$15 depending on the beers and book a one hour tour for $12.

Tours include a pint of beer at the end which is a fun way to enjoy your beer and learn a little bit about the process.

8. Eat a Chicago Dog

You can’t go to Chicago and not try a Chicago dog! The hot dog is topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers and a dash of celery salt. I recommend Portillo’s or Fastso’s Last Stand for a delicious one.

9. Go to a Real Speakeasy



Chicago has a major history with prohibition and many speak easies that were around in the 1920s are still around today. Green Door Tavern is home to one of these spots known as the Drifter. It’s located in the basement of the bar, and you’ve got to go through a bookcase next to the bathrooms to get in. Once inside, it’s a small bar with live entertainment happening every night. They have kept the vintage feel of the bar.

All the drinks are listed on tarot cards, and my boyfriend couldn’t stop ordering the Mizz McFlury because it was so good (okay, fine, I ended up ordering it too because YUM!). They also have live entertainment nightly and if you want to see what a speakeasy was like, this is the spot to do it.

10. Take the L Train for Views

The “L Train” is short for elevated and you’ll get a unique experience taking one of these trains. You’ll get the chance to see Chicago from above as you get from one destination to another.

Discover cheap and fun ways to explore Chicago. From budget-friendly attractions to affordable dining options.

So now you’re ready to take on the best of the city with these fun and cheap things to do in Chicago. Even if you’re traveling solo to Chicago, you’re sure to have some fun. What’s your favorite thing to do in Chicago?


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