10 Things to Do Your First Time in Chicago

So, you’re planning a visit to Chicago and you’ve never been there before. You’re wondering what you should see and do. Should you visit the classic tourist attractions or should you look for some more unique things to do? And how much is it all going to cost?

I’ve put together a list of the top ten things you should do during your first ever visit to Chicago. Some of them are a bit touristy, but these are attractions you want to make sure you see! These activities come at a range of prices, from $0 to $200, so there’s something for every budget. (Note that some of the prices I listed are approximations.)

The most important thing to remember when you visit Chicago is to enjoy every minute of it! Chicago is a beautiful city with a rich history and there is always something to do there! Once you leave, you’ll want to come back! Make the most of your visit with these ten activities!

1. See the city from 1,400 feet in the air.

The Chicago Sky Deck, located on the 103rd floor of the Willis Tower, is the highest observation deck in the United States. Stepping out into a glass box 1400 ft in the air is actually not as scary as it sounds, and totally worth the million-dollar view! There’s no better way to get a look at the vastness of the city! The historic Willis Tower is an absolute must see.

Price:

Ages 3-11: $15

Ages 12+: $23

2. Visit Millennium Park.

Take a walk in the park and get a look at some world-class art. Don’t forget to stop over at Cloud Gate (or the "bean" as we call it in Chicago) and snap a couple pictures! If you’re there in the winter, this is also a great place to go skating!

Price: Free!

3. Try deep dish.

This gooey, cheesy delight will be the best thing you taste for weeks! Stop inside a Giordano’s, Uno’s, Gino’s East, or Lou Malnati’s, and see what I mean. Don’t worry about the calories; you’ll get plenty of exercise walking around the city!

Price: $15–40

4. Visit The Art Institute and lots of other great museums.

Chicago is a hot spot for top-notch museums! My personal favorite is the Art Institute, located right downtown, one stop over from Millennium Park. If you happen to be in Chicago on a Thursday, the Art Institute is free from 5 to 8 PM. Also, while you’re there, you can see the start of Historic Route 66 right across the street! If you’re willing to take a trek South to the Museum campus, check out the Adler Planetarium, the Shedd Aquarium, the Field Museum of Natural History, the Museum of Science and Industry, and more!

Price: $10–30

5. Enjoy Lake Michigan.

Chicago is located on the shores of the beautiful and expansive Lake Michigan, and there are many ways to enjoy the lake. If you visit during the summer, go for a swim at Montrose beach, or, if you’re feeling brave, you can try taking a sailing lesson! If you’re looking for something more relaxing, you can take a cruise off of Navy Pier, or go for a walk on Chicago’s Lakefront Trail.

Price:

Beaches: Free!

Sailing Lessons: $75

Navy Pier Cruise: $25–200

Lakefront Trail: Free!

6. Ride the water taxi.

Not only does it get you from point A to B, it does so in a boat ride! It’s a great way to get to many destinations along the Chicago River, including Chinatown and Michigan Ave, and get a great view of the city while you’re at it! It’s an affordable and fun way to get where you’re going.

Price: $10 for a day pass

7. Shop on The Magnificent Mile.

The Magnificent Mile is located on Michigan Avenue, extending from the Chicago River to E Lake Shore Drive. Whether you’re looking for clothes, groceries, or electronics, you can find it on The Magnificent Mile! It’s also home to some great restaurants if you get hungry and hotels if you’re staying the night.

Price: Free to walk around, but bring money for shopping.

8. See a Broadway show.

If you like theatre, you’ll love Chicago! No matter when you visit, Broadway in Chicago always offers a great selection of shows to see. You can get in on the Hamilton craze if you’re willing to spend a bit of money! Or, if tickets for your favorite show are sold out, you can always go on the Historic Theatre Tours.

Price: $25–100

9. See a sports game.

Chicago’s got something for everyone when it comes to sports with two major league baseball teams, a great hockey team, a football team, a basketball team, and even a soccer team! Prices will vary depending on what team you see and when, etc., but seeing a sports game can be a great way to experience Chicago and show some pride for your new favorite city!

10. Walk along the river.

The Chicago River Walk is absolutely beautiful! After a long day packed full of Chicago adventures, a relaxing walk along the river might be just what you need! You’ll get a great view of the buildings and the boats passing by. As you walk, you may get to hear some live music by local bands.