Top 12 Things To Do In Winter In Chicago, Illinois - Updated 2024

things to do in winter in chicago
Contributing Writer
| 5 min read

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 to this city during winter and searching for famous hotels, you’re in luck, as you will have several options to choose from. Besides that, the city also has enough accommodation for those who want a gorgeous view. You can stay at any of the beachfront and lakefront hotels in Chicago as well. So, put your worries away and check out this list of the top things to do in winter in Chicago, Illinois.

1. Celebrate Christmas Eve on a cruise on Lake Michigan (from USD 184.13)

things to do in winter in chicago | celebrate christmas eve on a cruise on lake michigan

If you are looking for fun things to do for couples and families in Chicago, look no further! Venture on a joyful voyage this Christmas Eve with a gorgeous cruise across Lake Michigan, departing from the heart of Chicago. Enjoy a lovely three-course dinner at your exclusive table while a live DJ fills the atmosphere with music.

For 2.5 hours, soak in the beautiful sights of Chicago’s skyline and famous landmarks, such as Adler Planetarium and Navy Pier, from the observation deck. This cruise promises a festive atmosphere, top-notch service, and a special holiday experience for you and your loved ones.

Visited this place?

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

Duration: 2.5 hour

4 reviews

2. Warm up with a deep dish pizza at Giordano's

Editor's Note: Photo taken from the establishment's official social account

Repost from @lifesabrys • Did you really go to Chicago if you didn’t have their deep-dish pizza? The most delicious, heavenly tasting pizza

Posted by Giordano's Pizza on Wednesday, November 30, 2022

Take some time out this winter to visit Giordano’s in Chicago, where the deep-dish pizza reigns supreme, providing the ultimate comfort food. Each bite is a symphony of flavors, with the in-house aged Wisconsin Mozzarella delivering a creamy and buttery melt. Meanwhile, the specially farmed tomatoes from Mendocino County create a pizza sauce that’s simply unrivaled.

Enjoy a variety of pizzas, from hand-stretched thin crusts to stuffed pizzas. The chain also offers classic Italian dishes, starters, and desserts, ensuring there is something for every palate to enjoy.


Address: South Loop Branch - 1340 S Michigan Ave, Chicago, IL 60605, United States (has 15 stores in Chicago)

Website: Giordano’s

Opening hours: Sun - Thu: 11am - 10pm; Fri - Sat: 11am - 12am

Visited this place?

3. Go ice skating

things to do in winter in chicago | go ice skating
Source: instagram

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

Visited this place?

4. Enjoy festive the lights at Lincoln Park Zoo

Siberian Tiger Lincoln Park Zoo (17562834949)
Source: Photo by Wikimedia Commons user Mobilus In Mobili used under CC BY 2.0

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

Visited this place?

5. 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

Visited this place?

6. 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

Visited this place?

7. 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

Visited this place?

8. Go sledding through snowy parks

Editor's Note: Photo taken from the establishment's official social account

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,

Visited this place?

9. Shop your fill at Orland Square

If you are looking for the perfect shopping destination, then Orland Square Mall is one of the best places to visit in Chicago for your winter 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

Visited this place?

10. Warm up with a nice cup of hot chocolate

Editor's Note: Photo taken from the establishment's official social account

The weekend is close and it smells like fresh bagels!Get your preorders in by 10am tomorrow. You can always walkup and order, on Sat & Sun, starting at 8am.?? #xoMindy #bakery #pastrylove

Posted by Hot Chocolate Chicago on Thursday, March 4, 2021

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

Visited this place?

11. 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.

Visited this place?

Chicago Holiday Lights Trolley and Christmas Market Tour

Duration: 1 hour 30 minutes

12. 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.

Visited this place?

2.5-Hour Chicago Winter Holiday Walking Tour With Drinks

Duration: 3 hours (Approx.)

Discover Chicago in winter

Ice Skating
Source: Unsplash

Hop on an airplane, discover these best winter events and attractions in Chicago, and make the most of your time. Enjoy the city’s 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.

Frequently asked questions about things to do in winter in Chicago, Illinois

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.


Get Trip101 in your inbox

Unsubscribe in one click. See our Privacy Policy for more information on how we use your data

Michelle, a devoted writer and travel enthusiast, endeavors to make a living through her love for words. Her objective is to explore the world, connect with diverse individuals, and motivate others...Read more

 Want to contribute as a Local Expert?
Explore Chicago
Looking for accommodation?
Good things are meant to be shared!
Back to top
Visited any of these places? Click this button to activate our "Add a Tip" feature to share your experience.