Last Updated: Jan. 6, 2026
Winter in Chicago can bring harsh winds and freezing temperatures, but locals and tourists can still find plenty of activities to enjoy. Before diving into the full list of fun winter activities, remember that one of the best ways to experience the magic of the city in winter is from the warmth and comfort of the 360 CHICAGO Observation Deck. Standing 1,030 feet above the Magnificent Mile, you'll have the chance to see how magical the Chicago skyline and Lake Michigan are when they're covered in snow.
With just a bit of planning and preparation, people of all ages can have fun (and stay warm) during the Windy City's most frigid months. Here are 10 of the best things to do in Chicago this winter.
Even when there's not a lot of snow in the forecast, the hill by Soldier Field stays ready for sledding during winter months. If there's not enough natural snow, the hill is covered in artificial fluff! Only plastic sleds are allowed, and you'll want to call ahead to make sure the hill is open during your visit.
Ice skating is a popular winter activity in Chicago, and there are several seasonal outdoor rinks to choose from. Skating at the McCormick Tribune Ice Rink in Millenium Park is free (skate rentals available), but reservations are required. Reserve your ticket to skate down the Ice Skating Ribbon, a quarter-mile skating path in Maggie Daley Park. For a different view of the city, skate four floors off the ground at The Sky Rink located on the rooftop of The Peninsula Hotel.
The Windy City knows how to provide comfortable outdoor dining in any weather. Check out one of the many heated outdoor eating spots in the city for a delicious winter meal. Many Chicago restaurants get creative with greenhouses, igloos, and fire pits to keep their outdoor dining spaces open all year round.
Combine winter sports with tasty cocktails at The Gwen during winter months. The rooftop terrace is transformed into a curling rink when the weather gets cold, and rink reservations come with a drink to keep you warm while you play.
A stunning piece of architecture and a true hidden gem, the Chicago Cultural Center offers a beautiful, warm, and free indoor activity. Explore the world's largest Tiffany stained-glass dome at Preston Bradley Hall, view free art exhibits, and enjoy a variety of public programs and performances. It’s a perfect central location to warm up on a chilly Chicago afternoon.
Northerly Island Park is home to all kinds of outdoor activities, including snowshoeing in the winter. Head out to the peninsula for a snowy walk anytime the snow is deep enough. Be sure to check out the free Polar Adventure Days that happen every winter, where you can often rent snowshoes, see live animals, and check out winter-themed art.
Many Chicago museums offer free admission on certain days during the winter, so be sure to plan your visits accordingly. Spend the day viewing impressive art at the Art Institute of Chicago, exploring natural science and history at The Field Museum, or sparking curiosity at the Griffin Museum of Science and Industry.
Bundle up to see the polar bears, snow monkeys, and more cold-weather animals enjoying themselves during the winter at the Lincoln Park Zoo. You'll also be able to warm up in the many buildings that house animals from warmer climates.
Stay warm and connect with nature year-round at one of Chicago's indoor gardens. The Garfield Park Conservatory and the Lincoln Park Conservatory offer beautiful, warm escapes. Both are free to enter (though reservations are highly recommended/required for the former).
The Christkindlmarket is a German-style outdoor Christmas Market with free admission. You can shop for unique holiday gifts, sip hot cider and spiced wine, and enjoy the festive decorations. Be sure to check the calendar for special events and open dates for the upcoming 2026 season!
Don’t let the cold winter weather keep you from a visit to Chicago. There are plenty of opportunities for fun year-round! Stay cozy indoors or layer up for outdoor winter adventures. You can enjoy the coldest season of the year no matter what type of activities you prefer with all the fun things to do in Chicago in winter.
Experience the best of both worlds at 360 CHICAGO, where you can stay warm while enjoying panoramic views of the chilly city. Book your tickets now for your winter vacation (don’t forget to grab your coat!)
Like this Article? Pin it for later!
"*" indicates required fields
Click for Accessibility
