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Photograph: Grace DuVal

13 things to do outdoors this winter in Chicago

Don't let the cold weather keep you cooped up! Here's how you can enjoy the outdoors during the winter in Chicago.

Zach Long
Written by
Zach Long
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Winter in Chicago can quickly devolve into a barrage of frigid temperatures, slushy streets and icy sidewalks—but that doesn't mean giving up on things to do outside in Chicago. Throw on some boots and a heavy coat and find things to do outdoors this winter, such as a chilly visit to a Chicago park, a day on the ice rink in Millennium Park or a trip to Pilsen to see the 16th Street murals dusted in snow. If you're craving an escape from the city, you can find a spot for winter hiking, go skiing on a nearby hill or do some winter ziplining at The Forge adventure park. You don't need to stay cooped up until spring arrives—here's where you can find things to do outdoors during the winter in Chicago.

RECOMMENDED: Discover more things to do this winter in Chicago

Things to do outdoors in the winter

  • Things to do

Last year, ice skating options throughout Chicago were sparse, but nearly every major rink is back in action this winter. Head to Maggie Daley Park to do laps around the skating ribbon, zoom across the sizable rink at Midway Plaisance Park or take your skates to the Rink at Gallagher Way, directly next to Wrigley Field. Skate rentals are available at many rinks, but you can often skate for free if you bring your own.

  • Things to do

The Midwest is hardly a ski and snowboarding mecca, but you'll still find ample opportunities to hit the slopes within a few hours' drive of Chicago. Travel just outside of the city to check out local options or head north to Wisconsin for resorts in the hilly Driftless Area; you'll also find chic options in Michigan with cushy lodgings to make for a perfect winter weekend getaway.

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  • Kids

Don't let Chicago's overall flatness fool you—there are great sledding hills to be found in tons of the city's neighborhoods. Folks looking for a rush should check out the 200-foot slope tucked inside the Dan Ryan Woods nature preserve, which is lit and staffed by county employees when conditions are right (call head of time to make sure). On less snowy days, a hill located outside of Soldier Field is supplemented with machine-made snow. And if you've got little ones, you'll also find a variety of bunny hills perfect for beginners.

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  • Things to do
  • South Shore

The 18-mile path that hugs the shores of Lake Michigan is pretty sparsely populated during the winter months, save for the dedicated runners and cyclists that take advantage of the decrease in traffic. If you're willing to put on some layers (there's usually a bit more wind by the lake), you can't beat the sights along the Lakefront Trail, whether you're gazing north from Promontory Point or south from North Avenue Beach. Keep moving to stay warm—and maybe bring along a thermos of cocoa and some handwarmers.

Give curling a try
Photograph: Courtesy The Gwen Hotel

6. Give curling a try

You've seen it playing during the Winter Olympics, so why not give this slippery sport a try? Several different venues in Chicago offer the opporunity to play this variation of shuffleboard on ice, including the Gwen Hotel, which rents out a rink on its rooftop terrace ($30/person). You can also reserve a rink on the back patio of Kaiser Tiger ($70 for 40 minutes), at Whiskey Business ($25 per hour) or atop Lakeshore Sport & Fitness ($30 for 30 minutes).

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  • Things to do
  • Literary events
  • Suburbs
  • price 2 of 4

You certainly won't find any flowers blooming in the Chicago Botanic Garden during the winter, but the outdoor attraction maintains its regular hours during the winter. Swing by during the day to explore the garden grounds (non-members will need to make a reservation on teh Garden's website) and make sure to see the Orchid Show, which returns to a greenhouse from February 12 through March 27.

  • Attractions
  • Parks and gardens
  • North Park

Cold weather shouldn't stop you from taking advantage of one of the city's best paved trails. Beginning in Gompers Park and stretching all the way to the Skokie Lagoons, the North Branch Trail remains open from sunrise to sunset year-round, meaning that you can walk, jog or bike on it as long as conditions are favorable. Visit the Sidney Yates Flatwoods or take the trail all the way to the Chicago Botanic Garden.

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  • Things to do

Don't let the chilly weather keep you out of the city's public parks this winter. Even when there's not snow on the ground, the various green spaces (which are a bit more brown, at the moment) that make up the Chicago Park District are beautiful places to get some fresh air. Go see the Statue of the Republic in Jackson Park, climb to the top of "Mount Bridgeport" in Palmisano Park, do a lap around the lagoon in Douglas Park or make a playlist and pretend you're attending a self-curated edition of Pitchfork Music Festival in Union Park.

Put on a sweater and dine outdoors
Photograph: Paul Crisanti

10. Put on a sweater and dine outdoors

While most dining has gone back indoors this winter, there are a few spots throughout Chicago that are still offering igloos and other outdoor spaces. You can enjoy views of the Chicago River in private igloos at City Winery's Riverwalk location, dine inside a heated tent at the Duck Inn or reserve a spot in one of the "bubbles" on the patio at Fiya in Andersonville. Plus, plenty of our favorite restaurant patios have set up heaters or tents to ward off the winter chill.

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  • Things to do
  • Suburbs

Not into sliding down slopes on your skis? You can do some cross-country skiing at the Morton Arboretum, where guests can bring their own skis and enjoy some of the trails that wind through the greenspace. From January 15 to March 21, skis and snowshoes are available to rent, but only when there is more than four inches of snow on the ground. Remember that timed-entry admission is still required for all Morton Arboretum guests—you can make a reservation online.

  • Things to do

Chicago's best public art doesn't go indoors when the conditions outside take a turn for the frigid. If you dress for the weather, you can treat the city's various public displays like an open-air museum, stopping by the Picasso and Calder sculptures in the Loop or checking out the murals lining 16th Street in Pilsen. You may need to trudge through some snow, but the city's walkable art gallery is 100 percent free.

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  • Things to do

Throw on some layers and head to state parks and forest preserves surrounding the city, most of which welcome visitors throughout the winter. You can travel to Starved Rock and admire the frozen waterfalls, gaze out at the icy Lake Michigan from the Indiana Dunes or visit the bison at Midewin National Tallgrass Prairie. Make sure to double check the operating hours wherever you're visiting—some parks and preserves make adjustments during December, January and February.

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