The Top 9 Things to Do in Chicago in the Winter

Hug a Tree at The Morton Arboretum

Illumination: Tree Lights at The Morton Arboretum is one of the most unique and fun activities to brighten up the Chicago winter. Walk along a paved one-mile path as you watch a light show like no other. Warm up with a cup of hot chocolate, roast marshmallows around a fire, and immerse yourself in a hands-on outdoor experience under the trees. Sing along during the live entertainment during the week.

Plan on spending nearly two hours at the arboretum and dress warm for a pleasant experience. Download the free Morton Arboretum app to launch the Illumination tour.

Take in Urban Views From a Rooftop or Along the River

Just because it’s chilly in Chicago during the winter months, that doesn’t mean you can’t go outside and enjoy the city’s stellar urban views. Boleo Rooftop Bar and Lounge in the Kimpton Gray Hotel, brings the warmth of South America to the city of big shoulders. Enjoy Argentinian and Peruvian-inspired dishes while sipping Pisco. You’ll be cozy under the glass retractable roof.

City Winery Chicago at the Riverwalk is also a great choice for the winter months. Bring a group of friends and hang out in one of the bubbles, situated along the Chicago River, and enjoy a bottle of wine from the well curated list.

If Art Deco architecture paired with city views is your thing, then Upstairs at The Gwen will surely delight your senses. Visit the Curling Cabin, try your hand at the sport of curling, and warm up around the fire pits.

Cheer on the Chicago Blackhawks

All winter long, you can head to the United Center and catch a family-friendly professional ice hockey game. Cheer on the Chicago Blackhawks, winners of multiple Stanley Cup championships; snap photos with the mascot, Tommy Hawk; and sing along to “Chelsea Dagger” by The Fratellis, the official team goal song.  

The United Center is also close to many excellent restaurants and bars like Monteverde Restaurant and Pastificio, WestEnd (they have a shuttle that will take you to the United Center), Bonci Pizza, and Mad Social. 

Ice Skate in the City

From November to March, you can ice skate with your family in tow at McCormick Tribune Plaza and Ice Rink. Free and open to the public, skating here is a holiday tradition and a favorite winter pastime for many Chicagoans.

The Maggie Daley Park Ice Ribbon is a big hit for outdoor winter fun, free to the public.

The Peninsula Chicago is also a lovely, less crowded, location for ice skating lovers. The rink’s heated lounge offers hot cocoa and cider. 

Bring Your Loved Ones to the Walnut Room at Macy’s

Having a drink or meal at The Walnut Room at Macy’s is a quintessential Chicagoan experience during the winter months, from late November through early January. This is the very first restaurant ever opened inside of a department store. Tables are situated around a large holiday tree. Signature dishes include pot pies and French onion soup. 

Laugh at a Comedy Show at The Second City

Chicago is practically synonymous with comedy, and The Second City is practically a feeder for Saturday Night Live. During the winter, you can see a variety of comedy shows, including "Deck the Hallmark: A Greeting Card Channel Original." This two-hour holiday movie parody is a great option for a ladies night out, date night, or for big laughs with a family full of grown-ups (it’s rated R). This holiday show runs from the middle of November through the end of December. 

Wander Through the ZooLights Wonderland at Lincoln Park Zoo

Chicago has so many opportunities to embrace the winter and get outside and the Lincoln Park Zoo is definitely one of the winter highlights in this city. Wander through millions of lights, past hundreds of 3-D displays, and enjoy festive activities like ice sculpting viewing during this special winter wonderland.

Mondays in December are Family Nights where you can enjoy special discounts and activities. Food and beverages are available to keep you satiated as you make your way through the ticketed activities like the AT&T Endangered Species Carousel, Lionel Train Adventure, Light Maze, Cookie Decorating at the Patio at Café Brauer, and Century Wheel.

Dec. 3 is the Holiday Market at the Zoo, Dec. 5 is the Adult’s Night Out: Holidaze event, and Breakfast with Santa is Dec. 15. 

Sip Spiced Wine and Shop at Christkindlmarket Chicago

Dress warm and head to Chicago’s Daley Plaza, in the loop, where every year you can sip warm drinks, nosh on German treats, and shop for holiday-themed goods. International and local vendors sell their wares out of little German-inspired huts, lined with twinkling lights, creating a fun family-friendly atmosphere.

Admission to the market is free, but bring cash because some of the vendors don’t accept credit cards. 

See Christmas Trees From Around the World at the Museum of Science and Industry

Learn about other cultures and holiday traditions at the Museum of Science and Industry’s "Christmas Around the World and Holidays of Light" winter exhibit. Not only is there a grand floor-to-ceiling tree, but also, there are about 50 holiday trees representing traditions from around the world.

Live performances and special happenings make the holiday season bright at the museum.