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Ah, the Windy City! Recently named as one of the best cities in the world by Time Out Magazine, Chicago is a great destination any time of year. There are endless things to do in Chicago.

With great restaurants, the Magnificent Mile, and a stunning skyline, you don’t want to miss out on this premiere location. Here are fun things to do in Chicago and the best places to see on your next trip to the city! Oh and if it’s winter, make sure you bundle up!

Make sure to check out these amazing travel hacks for a smooth trip.

6 Fun Things To Do In Chicago With The Family

With great restaurants, the Magnificent Mile, and a stunning skyline, you don't want to miss out on this premiere location. Here are fun things to do in Chicago and the best places to see on your next trip to the city! Oh and if it's winter, make sure you bundle up!

The Magnificent Mile

This website describes “The Magnificent Mile” as “the 13-block stretch of North Michigan Avenue that runs from the banks of the south, to Oak Street to the north”. It’s home to more than “460 stores, 275 restaurants, and 60 hotels”.

Architecture Tours 

I have been dying to take the architecture tour along the river! It’s been called the “top tour in Chicago and one of the top ten tours in the U.S.”, according to TripAdvisor. The tour is an hour and a half, and in that time you will learn about more that 50 buildings that line the river. It’s honestly stunning!

6 Unforgettable Things To Do In Chicago With The Family Click To Tweet

Pizza

Duh. I mean, need I say more? Whether you prefer deep dish or thin crust, we have it all. Some places to check out include Lou Malnati’s (the Malnati salad is delicious!), Pizano’s, Gino’s East, Pizzeria Uno, Pizzeria Due, and Piece Pizza in Wicker Park!

John Hancock Observatory

Let me tell you, the views here are beautiful! You’ll get to see an amazing view of Chicago all around. Tickets are a bit pricey for a quick trip ($14 for kids ages 3-11, $21 for ages 12 and up, and free for children under 3). My suggestion would be to relax and stay awhile! Grab a drink at the bar and enjoy the view. There is also a restaurant, The Signature Room at the 95th, on the 95th floor of the building. Make sure to make a reservation!

6 Unforgettable Things To Do In Chicago With The Family

Millennium Park

This spot can be a bit touristy, but nonetheless it’s still worth the trip! Check out Cloud Gate (also known as “The Bean”) and take a mirror selfie. Go ice skating in the winter, or simply wander around. The park is filled with both tourists and locals alike. 

Art Institute of Chicago

Located in Grant Park, adjacent to Millennium Park, you’ll find that Art Institute of Chicago. It’s one of the oldest and biggest art museums in the U.S. and holds almost 300,000 works of art. You definitely don’t want to miss out on this cultural icon. Who knows, you may even run into Ferris Bueller!

Those are just a few fun things to do in Chicago! Be sure to check out everything this amazing place has to offer!

Kristen May
Kristen May
Kristen is a rising senior year at DePaul University in Chicago, studying communications. She has a passion for health and wellness, and a weakness for good crime stories. When she's not working or studying, you can find her with a glass of rosé in her hand!