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Winter in the Windy City


Many might not realize it, but Chicago is a great place to visit during the winter. Yes, temperatures drop dramatically, and the Windy City gets…well, cold and windy. However, there are plenty of fun, festive activities that will help you forget the cold and get in the holiday spirit. Here are our picks for the best winter activities in Chicago.

Skate at McCormick Tribune Ice Rink

Stop by Millennium Park and lace up your skates for ice skating at McCormick Tribune Ice Rink. Located right in front of The Bean, the rink is a picture-perfect spot to visit. A heads up: Admission is free but online ticketed reservations are required.

Warm Up at Garfield Park Conservatory

Locals know about Garfield Park Conservatory, but visitors might be aware that the lush spot is one of the largest botanical conservatories in the U.S. Stop by to enjoy tropical temperatures and tour eight indoor display gardens. The Winter Flower Show, Serenity, takes place from November 24, 2021-January 9, 2022. Tickets to the conservatory are free but advanced reservations are required.

Go Sledding at Soldier Field Sledding Hill

Indulge your inner child and take a sled down Soldier Field Sledding Hill. The 33-foot, lightning-fast slope offers a thrilling ride and panoramic views of Lake Michigan.

Watch Digital Art at Art on the Mart

Fans of contemporary art will enjoy Art on the Mart. Located outside The Merchandise Mart in downtown Chicago, the display is the largest permanent digital art projection in the world. Visitors can stop by to watch a free 30-minute program, which is shown nightly at 7:30 and 8 PM through December 30.

Go Curling at The Gwen

Some of us may have only experienced curling by watching the Winter Olympics, but you can try the sport yourself in Chicago. Visit the Gwen Hotel on Michigan Avenue to play on their custom-designed iceless Curling Rink on their rooftop terrace. The rink gets bonus points for its stunning skyline views. Reservations are required.

Take a Stroll on the Lakefront Trail

Even though it may seem counterintuitive, a stroll along the Lakefront Trail during the winter can’t be beat. Bundle up and take in stunning scenery along Lake Michigan without the usual crowds. Make sure to bring a thermos of hot chocolate to warm up during the walk.

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