15 Things to Do in Chicago During Winter

If you’re ready to brave the Chicago winds and visit this historic city in the dead of winter, then you deserve a pat on the back and an extra cup of hot cocoa. Although it’s known for its chilly temps this time of year, there are still many ways to embrace the warmth of one of America’s finest cities. 

Below, we’ll take you through some indoor and outdoor activities, depending on how much you’re ready to bundle up. From free ice skating, sleigh riding, and polar bear meetings to cozy rooftop bars and indoor gardens, there are plenty of ways to see the sights and snap some iconic photos of the city’s skyline. 

Ice Skate in Millennium Park

Millennium Park, known for its stunning views of downtown, sets up the McCormick Tribune Ice Rink from about mid-November to early February each year – depending on the weather. It’s free if you bring your own skates, and they also offer free lessons on Saturdays and Sundays from 9 am to 10 am. This is definitely something to take advantage of because, again, those views of the Chicago skyline, as well as Michigan Avenue, will stay with you forever. 

Sleigh Ride Near Soldier Field

It won’t take you long to find the sledding hill near Soldier Field – home of the Chicago Bears. It’s right there on a stretch of parkland surrounding the stadium, near the north end of the south parking lot. Bring your own sled – as long as it’s plastic – and get ready to bring back all the warm and fuzzies we used to feel as a kid gliding down a hill on a snow day from school. 

Visit Lincoln Park Zoo

Despite how cold it gets in Chicago, the Lincoln Park Zoo is open all year round. You don’t have to freeze your tailfeathers off when you’re here, though. Many of the animals move indoors, so you can say hello from warmer climates, as well. But, some of the guys that love the cold, like the polar bears and penguins, remain outdoors, and you can see what they’re up to when the temperatures drop. As an added perk, this, too, is a free activity! 

Stroll Around Lincoln Park Conservatory

After the zoo, ready for another free activity? Since you’re nearby, dip into the Lincoln Park Conservatory to feel the warmth and see some exotic foliage. It’ll certainly provide a nice escape from the cold as you breeze past some tropical palms and ancient ferns. Right now, there’s a lovely Winter Flower Show going on, featuring a huge display of pretty poinsettias to get everyone in the Christmas spirit.