Chicago Winter Activities

Chicago Winter Activities

The Best Things to Do in Chicago This Winter

Explore the city like a local and experience all there is to do near our South Loop hotel this winter. Check out our list of the best Chicago indoor and outdoor winter activities below and indulge in all the Windy City has to offer. 

Looking for even more adventures? Head over to our 125 Reasons for the Seasons activities page, where you will find our curated list of 125 activities to enjoy this winter during your trip to Chicago. 

Millennium Park

Visit Millennium Park, filled with inspiring public art pieces, fun outdoor activities, and more. Take a selfie with a friend at The Bean (aka "Cloud Gate") or take a spin on the ice at the McCormick Tribune Ice Rink, a Chicago winter tradition, now in its 19th season. Nearby Millennium Park, visit the world’s largest Tiffany Dome, composed of 30,000 stained-glass pieces, which crowns the neoclassical 1897 Chicago Cultural Center. Go on the Tiffany Treasures Tour, hosted by Chicago Architecture Center, to learn more about this magnificent installation and more. 

Ravenstel Photographic Millennium Park Photo courtesy of Choose Chicago.

Museum Campus

Explore indoor wonders at one of Chicago’s renowned museums. The Blackstone is conveniently situated near Museum Campus, located along Lake Michigan. Pro tip: You'll enjoy one of the best skyline views along the Lakefront Trail in front of the Shedd Aquarium. Look for our unique building and our famous green rooftop!


Tour Chicago’s first craft distillery, KOVAL. Learn about the differences between white and aged whiskey, the subtle intricacies of distillation, and the delicious beauty of small-batch spirits. See where each and every step of the process takes place. Tasting of numerous spirits is just one of the perks! Planning to stay the night? Check out our current "Tapping the Barrel" offer, complete with overnight accommodations, an Uber gift card, and a private KOVAL tour and tasting.

American Writers Museum

More of the literary type? Find your words at the American Writers Museum. In the heart of downtown Chicago, the American Writers Museum celebrates all genres of writing through interactive exhibits and programming. You can even get a taste before you go — a vintage typewriter from the museum is on display in The Blackstone's lobby.

Relive "Ferris Bueller’s Day Off"

"Ferris Bueller’s Day Off" is a quintessential Chicago movie. Relive the film by visiting some of its more recognizable and iconic locations, including Grant Park, Lake Shore Drive, Italian Village, Willis Tower, Chicago Board of Trade, The Art Institute of Chicago, and Wrigley Field. Pro tip: Wrigley Field offers stadium tours during the off-season, so even if you can't catch a game, you don't have to miss out!

Get Lost in Local Art

Chicago is a living canvas — literally. Discover all the unique murals tucked in various spots around the city. The Wabash Arts Corridor, featuring large-scale murals, is right near The Blackstone. You'll find it on Wabash Avenue, from Van Buren to Roosevelt, and framed to the east by Michigan Avenue and to the west by State Street. After exploring, warm up at Chicago’s iconic Eleven City Diner.

Indulge in Deep Dish

Chicago is known for its deep-dish pizza. But what restaurant reigns supreme? You be the judge! Warm up with a deep-dish pizza from one of Chicago’s favorite pizza joints: Giordano’s, Lou Malnati’s, and Pequod’s Pizza are three of the most popular. Let us know your favorite!