Skip to Content

What to Do in Chicago During Winter

A guide of what to do in Chicago during Winter, these activities and events are the perfect way to make the most of a cold time of year.

A guide of what to do in Chicago during Winter, these activities and events are the perfect way to make the most of a cold time of year.

Heads up – what to do in Chicago at Christmastime is a separate list.

It can get very cold in Chicago during the winter. On top of that, Chicago winters are long. It can make people a little stir crazy. This list will help you to get out of the house and forget how cold it is outside.

What to Do in Chicago During Winter

Seasonal Events and Activities

These events and activities take place throughout the winter and don’t require much advance planning.

*Insider Tip: Scoop Up Canceled Reservations on a Snowy Day

Snowy days can be the best time to visit Chicago’s most popular restaurants. Often, people who don’t live nearby will cancel their reservations and there will be few walk-ins. You can make calls day-of to see if you can score a reservation, or you can try walking in early (try before 6 pm).

Go to a Bulls or Blackhawks Game

Head to the United Center to cheer on the Bulls or the Blackhawks. Even if you don’t love hockey, the electric atmosphere of a Blackhawk’s game will win you over.

Check out a Food Hall

Chicago has several food halls and they are perfect places to visit on a cold day. Time Out Market, Urbanspace, and the Chicago French Market have the most food stalls. Heads up that Urbanspace is closed on Sundays.

Go Ice Skating

The ice rinks at Millennium Park and the ice ribbon at Maggie Daley Park are both open from November 19th through the start of March. There are also rinks at Gallagher Way, Navy Pier, and the Peninsula Hotel.

Visit a Museum

Chicago has several incredible museums where it is easy to spend a full day. You can see Sue at The Field Museum, visit the sharks at the Shedd Aquarium, learn about space at the Adler Planetarium, or explore a German U-boat at the Museum of Science and Industries – and that’s just the museums on Museum Campus. If you love art, visit the Art Institute or the Museum of Contemporary Art. The Chicago History Museum is a fun place to learn about our city’s history and it is smaller and can be seen a couple of hours.

Take a Cooking Class

Learn to make pasta at Tortello or check out one of the many classes offered by The Chopping Block which offers in-person and virtual classes.

Visit a Marshmallow Cafe for Hot Chocolate and S’mores

XO Marshmallow is a cafe that celebrates the marshmallow. The cafe serves hot chocolate plus a variety of s’mores and lattes.

Take in the Views from Centennial Wheel at Navy Pier

You can enjoy 360 degree views of Chicago from the Centennial Wheel. This Ferris wheel has climate controlled gondolas so you don’t need to worry about getting cold. This would be a wonderful way to admire the city on a snowy day.

Smell the Flowers at the Garfield Park Conservatory or the Lincoln Park Conservatory

The Garfield Park Conservatory is larger and specializes in growing exotic plants. Their Show House changes throughout the year and other displays include the Palm House, the Fern Room, the Desert House, and the Aroid House. It is a fun way to spend time in nature while still being inside. The Lincoln Park Conservatory is within Lincoln Park and is where plants and flowers are grown to be planted within the park in the Spring.

The Garfield Park Conservatory and the Lincoln Park Conservatory are open Wednesdays through Sundays. Admission is free but you should reserve tickets to the Garfield Park Conservatory in advance.

Shop Indoors at an Urban Mall

Chicago has a few urban shopping centers where guests and shop a variety of stores without needing to step outside. For more upscale retailers, visit 900 North Michigan Shops or the Shops at North Bridge. Water Tower Place is home to American Girl Place, Express, Forever 21, Lego, and some more affordable shops. All of these shopping centers are located along the Magnificent Mile.

If you want to find deals on designer items, visit the Fashion Outlets of Chicago in Rosemont where you can find shops including All Saints, Armani, Bloomingdales, Burberry, Coach, Cole Haan, Gucci, Jimmy Choo, Lululemon, Prada, Saint Laurent, Theory, and more.

Check out a Concert

You can opt to see a show at a bar like the Green Mill, Phyllis’s Musical Inn, the Empty Bottle, or Kingston Mines – these spots don’t require tickets just a cover at the door. If you want to plan ahead, check out the schedules at The Vic, Thalia Hall, City Winery, The Aragon Ballroom, The Chicago Theater, or the United Center.

Unwind with a Spa Day

For a spa experience with friends, check out Aire Ancient Baths. This beautiful space has a variety of baths with different temperatures and experiences. One is indoor/outdoor, one has music playing under the water and is salty so that you float, others have jets. There are also scented steam rooms, and massages are available.

Or, for a solo spa day, visit Kohler Waters Spa in Lincoln Park. This luxurious spa has a thermal suite, sauna, and plunge pool for guests to enjoy before or after their water services, massages, or body treatments. For something unique, try a hydrotherapy treatment which combines water treatment with massage.

Visit a Tiki Bar

This tiki lounge in the basement of Bub City in River North serves tropical cocktails that will help you forget how cold it is outside.

Try an Escape Room

Chicago has a handful of escape rooms. At The Quandary you are trapped on an island and surrounded by blood-thirsty dinosaurs. PanIQ Room has locations in Logan Square and the West Loop exploring themes including Prohibition-era Chicago, magic and wizardry, and voodoo priests. Fox in a Box has bunker, bank, and prison themed experiences. Escape Artistry has games set in the future, and with pirate and mobster themes.

Partake in a Tipsy Tea Party

The Gwen Hotel in River North offers an afternoon tea package that includes bottomless boozy tea or bottomless Prosecco for a 90 minute experience along with a tea tower featuring snacks like scones, crostini, and desserts.

Go on a Food Tour

Food Planet Chicago offers neighborhood and food themed tours. You can opt to explore Chinatown, visit the West Loop, taste tacos and tequila in Pilsen, have Bloody Marys and brunch in Wrigleyville, or more.

Visit a Rooftop Bar

During the winter in Chicago, some hotels and restaurants get creative with their rooftop spaces. You can sip cocktails in a ski chalet on the roof of Whiskey Business in Wicker Park, hang out in an igloo at the I/O Godfrey or London House, or stay warm by at fire pit at Aba.

Tour a Local Brewery

Did you know that Chicago has more breweries than any other city in the country? There are over 160! Some breweries offer tours and tastings, while others just have tasting rooms. Some of the more popular breweries are Revolution, Maplewood, Metropolitan, Goose Island, Half Acre, Lagunitas, and Dovetail.

Play a Game

The Chicago Athletic Association has a beautiful game room on the second floor of the hotel that is open to the public. You can play billiards, shuffleboard, chess, checkers, or bocce. Or if you want to play arcade games, visit Emporium or Headquarters Beercade. SPIN and AceBounce are both ping pong bars. You can bowl at Diversey River Bowl and Luck Strike. Big Mini is a bar with a 9 hole mini golf course. Or if you want to play indoor golf, head to Top Golf, Play18, or Five Iron Golf.

Try Indoor Rock Climbing or Indoor Skydiving

Get your adrenaline pumping! Brooklyn Boulders has locations in Lincoln Park and the West Loop that offers intro classes, class packs, and membership. iFly in Lincoln Park offers indoor skydiving experiences and classes.

See a Show

Chicago has a lively theater district and it can be a bit easier to get tickets in during the winter when he tourists aren’t as plentiful. Visit Broadway in Chicago to see what’s on and to purchase tickets. In general, there are usually 3-6 shows in Chicago.

Join a Curling League

Players Sports & Social Club has a curling league that competes on the rooftop of Whiskey Business in Wicker Park. You can join as an individual, small group, or full team. If curling isn’t your thing, you can try dodgeball, bowling, basketball, or indoor volleyball.

Go to a Speakeasy

Speakeasies feel cozy and romantic – they seem to transport you to a different time a place. Chicago has several speakeasies, some of the most popular are Bordel, The Drifter, Untitled Supper Club, the Violet Hour, Blind Barber, and Room 13.

Try Axe Throwing

Bad Axe Throwing has locations in Lakeview or West Loop. You can walk in, reserve a lane, or join an axe throwing league.

Visit the Chicago Magic Lounge

Hidden behind a laundromat in Andersonville you will find this bar and magic theater. There are shows nightly, and a variety of shows on the calendar. There is a music and magic show, showcases with multiple magicians, a performance bar, and nights when solo acts take the stage.

Laugh the Night Away at a Comedy Show

Chicago is home to many comedy clubs and theaters. You can opt to see improv at Second City, the Annoyance Theater, The Comedy Club House, or Comedy Sports. Or see standup comedic at Zanies, the Laugh Factory, or The Comedy Bar.

Special Events

These are wintertime events that happen on specific dates. You may need to purchase tickets in advance.

Chicago Restaurant Week

Chicago restaurant week usually lasts longer than a week, often starting in mid-March and ending in the beginning to April. During restaurant week, participating restaurants offer multi-course brunch or lunch for $25, or a multi-course dinner for $39 or $55. It’s a great opportunity to try new restaurants and enjoy some discount pricing. Reservations highly recommended, popular restaurants book up quickly.

Visit an Indoor Farmers Market

Both the Green City Market and the Wicker Park Farmers Market move indoors during the winter. Visit the websites for exact dates and locations.


The CHIditarod is a shopping cart race and food drive inspired by the dogsled race the Iditarod. It takes place in early March and tickets are required. Usually teams dress in elaborate costumes and decorate their shopping cart.

Renegade Craft Fair

This massive craft fair featuring local makers has an indoor event each winter. The schedule and location changes from year to year – it’s usually before Christmas making it a perfect opportunity to purchase unique gifts.