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Things To Do In Winter In Chicago, Illinois, USA - Updated 2020

things to do in winter in chicago
Michelle Jamie
Michelle Jamie
Updated

One of the largest cities in the United States, Chicago is an appealing destination during the winter, with its snowy parks, festive streets, and towering skyscrapers. It is famous for its tall buildings that dominate its skylines, which include John Hancock Center, Willis Tower, and the Tribune Tower with a neo-Gothic style. You can also find numerous iconic museums like the Art Institute of Chicago, which exhibits a collection of Impressionist and Post-Impressionist works. In case you’re traveling in this city during winter, read on and discover 10 things to do during winter in Chicago.

1. Go ice skating


Chicago is one of the best places to be, when it’s winter, because of its wide selection of skating rinks to choose from. There’s no need for you to be bored at home, under the blankets, when you can go and skate your heart out while listening to holiday music in the background. Aside from the music and the holiday feeling, you’ll also have an amazing view of the city skyline when you choose to skate at McCormick Tribune Ice Rink in Millennium Park. They offer free admission, but you have to pay for the skate shoes rental if you don’t have one. Other skating rinks in the city that deserve a visit are the Ice Skating Ribbon at Maggie Daley Park and Sky Rink at Peninsula Chicago.

Millennium Park

Address: 201 E Randolph St, Chicago, IL 60602, USA

Opening Hours: Mon-Sun: 6:00am–11:00pm

Website: Millennium Park

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2. Enjoy festive the lights at Lincoln Park Zoo


If you’re feeling festive and want to have a romantic date with your special someone, or you want to go out with your family for some quality time, then strolling around the Lincoln Zoo is a must. During the winter time, from late November to early January, the zoo transforms into a winter wonderland with thousands of twinkling lights, decorated trees, multicolored poinsettias, and more. It also features ice carving exhibits, carolers, and a spectacular light show. And, it is all for free. So what are you waiting for? Bring everyone to this special place and have a wonderful time ahead.

Lincoln Park Zoo

Address: 2001 N Clark St, Chicago, IL 60614, USA

Opening Hours: Mon-Sun: 10am to 5pm

Website: Lincoln Park Zoo

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3. Ride a horse-drawn carriage


Are you looking for an excellent date idea during the winter season? If so, the horse-drawn carriage tour of downtown is the best idea you can ever come up with. On your ride around downtown, pass streets with festive decor, twinkling lights, and colorful holiday markets. This activity will surely make a memorable experience for you and your partner. There are also lots of tour companies that offer horse-drawn carriage rides, all year round, but the best time to do it is during the Christmas season.

Chicago Horse & Carriage

Address: 806 N. Michigan Avenue, Chicago, IL 60611

Website: Chicago Horse & Carriage

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4. Browse through the Christmas markets (from USD 28.0)

Another popular thing to do in Chicago during the festive season is Christmas market hopping. If you’re still wondering what gift to give or are having a hard time picking up holiday decors, then this activity is a sure win for you. You don’t only get to witness beautiful festive sceneries but also finish your to-gift-list. Holiday markets that you should visit include Christkindl Market, Renegade Craft Fair, Randolph Street Market Festival, and lots more.

Chicago Holiday Lights Trolley and Christmas Market Tour

Duration: 1 hour 30 minutes

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5. Visit The Museum of Science and Industry for their 'Christmas Around the World' exhibit


If you love the Christmas holiday and want some inspiration for your holiday decors, then you have to visit the Museum of Science and Industry for their “Christmas around the World” exhibit. It is an exhibit featuring a collection of trees from different cultures adorned with decorations such as twinkling lights, poinsettias, balls, and more. Each of these more than 50 trees features unique ethnic style. The exhibit is open annually from mid-November to early January.

The Museum of Science and Industry

Address: 5700 S Lake Shore Dr, Chicago, IL 60637, USA

Opening Hours: Mon- Fri:9:30AM–4PM/ Sat-Sun:9:30AM–5:30PM

Website: The Museum of Science and Industry

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6. Stop by 'Winter Wonderfest' at Navy Pier


Located in the Chicago Shoreline, Navy Pier is a 3,300-foot-long (1,010 m) area that contains parks, gardens, shops, restaurants, family attractions, as well as hold holiday-themed events like the Winter Wonder fest. It is an annual event that features carnival rides, monstrous slides, indoor ice-skating rinks, fireworks shows, live performances, and more. This event is perfect for the whole family and it runs from November 30, 2018 – January 6, 2019. You will surely have a lot of fun here.

'Winter Wonderfest' at Navy Pier

Address: 600 E Grand Ave, Chicago, IL 60611, USA

Website: ‘Winter Wonderfest’ at Navy Pier

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7. Go sledding through snowy parks


Are you one of those people who aren’t a fan of winter because you dread not being able to go out a lot, and also because you can’t think of anything to do? Then, why not try having fun with snow? So, you’ve already done ice skating in many parks. Take advantage of the season and go sledding in a snowy forest or a snowy park, with your friends. If you’re wondering where, try the Cook Country Forest. They have plenty of sledding areas there, which can accommodate a crowd, including Swallow Cliff in Palos Park. For a more accessible choice, you can sled in one of the parks in Chicago Park District.

Chicago Park District

Address: 541 N. FairbanksChicago IL, 60611, USA

Opening Hours: Mon-Sun: 6AM–11PM

Website: Chicago Park District,

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8. Shop your fill at Orland Square


If you’re short on your shopping list, then Orland Square Mall is the solution for your holiday shopping rush. Located in Orland Park with lots of shopping strips and restaurants, you will surely have a fun shopping experience while you’re here. During the holiday, the mall features a festive mood with its cheerful atmosphere and Christmassy decor, making its shoppers long for this time of the year. It is also complete with the famous clothing brands, designer stores, and more.

Orland Square

Address: 288 Orland Square Dr, Orland Park, IL 60462, USA

Opening Hours: Mon-Sun: 10AM–9PM

Website: Orland Square

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9. Warm up with a nice cup of hot chocolate


Do you know what a cold winter calls for? It shouts in earnest for an excellent cup of hot chocolate. Go on a café hop in Chicago’s downtown, for the hunt of the best hot chocolate in town. After you’ve found one, stroll the area, with a cup in hand, and see the beautiful festive displays all around the town. Or you can get cozy in one of the cafes and have a fun time reading a book or munching on some snacks that go well with a hot chocolate like a pastry, perhaps.

Hot Chocolate Chicago

Address: 1747 N Damen Ave. Chicago, IL 60647

Opening Hours: Brunch- Sat & Sun: 10am-2pm/ Lunch- Wed-Fri: 11:30am-2pm/ Dinner & Dessert Tue-Thurs: 5:30pm-10pm Fri & Sat: > 5:30pm-12am Sun: 5:30pm-10pm

Website: Hot Chocolate Chicago

Katherine Anne Confections

Address: 2745 W. ARMITAGE, CHICAGO, IL 60647

Opening Hours: 11-7 TUE & WED, 11-9 THUR & FRI, 10-9 SAT, 11-5 SUN, CLOSED MON

Website: Katherine Anne Confections

See our full list of recommended Hotels in Chicago, Illinois, US and also compare the prices with Vacation Rentals in Chicago, Illinois, US

10. Sign up for festive walking tours (from USD 34.0)

things to do in winter in chicago | sign up for festive walking tours

Chicago during winter and the festive season is a sight to behold. So, grab a hot chocolate and join a walking tour of Chicago’s festive streets. There are plenty of holiday spots here, including Chicago’s traditional Christmas Tree, Cultural Center, the Marshall Field’s holiday window display, and more. Usually, this kind of tour lasts for one to two hours. There are also walking tours that you can join for free, or for a more relaxed sightseeing tour, make your own itinerary and in that way, you can cover a lot of area without worrying about your companions.

2.5-Hour Chicago Winter Holiday Walking Tour With Drinks

Duration: 3 hours (Approx.)

See our full list of recommended Hotels in Chicago, Illinois, US and also compare the prices with Vacation Rentals in Chicago, Illinois, US

Discover Chicago in winter

Ice Skating
Source: Unsplash

Hop on that airplane and discover Chicago during winter, with its festive streets, snowy parks, hot chocolate serving cafes, vibrant holiday markets, and interesting annual events like the Winter Wonder Fest and the Christmas Around the World at the Museum of Science and Industry.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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I am a book-loving travel-junkie who tries to write for a living. My goal is to explore the world, get to know as many people as I can, and inspire others to do the same, for the world is brighter...Read more

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