15 Fun Things to do in Chicago in Winter

15 Fun Things to do in Chicago in Winter

15 Things to do in Chicago in Winter

It’s magical how a city transforms during the holiday season. Chicago is a beautiful city in the summer, but in the winter, with its sparkling snow, twinkling lights, and myriad of attractions and events, it comes alive even more. 

Here are a few things to know about visiting or living in Chicago during the colder months, and a roundup of some of the best attractions, events, and fun things happening around the Windy City:

Should I visit Chicago in the Winter?

One of the best things about visiting any city is seeing it light up in the winter. Chicago lights up with activity and Christmas lights. Winter road trips to Chicago are a great way to enjoy Illinois state. Just don’t be put off by the cold and wind. Just pack a warm coat to keep you cozy while you explore.

Here are some expert tips on choosing a great, warm winter coat.

Things to do in Chicago in the winter: Sports

Feel the need to stretch your legs in Chicago? Here are some fun places to visit in this beautiful city:

1. Ice Skating

The best thing about ice skating is that most places offer skate rentals, so you just need to bundle up with a warm jacket and gloves before hitting the ice skating rink. Chicago boasts several outdoor rinks as well as a skating ribbon at Maggie Daley Park

Admission and skate rentals are reasonable at most spots. Some also offer free admission (like Warren Park rink) or free rental of specialty sleds so people of all abilities can enjoy the rink together.

Places to ice skate in Chicago:

2. Curling

Can’t skate? Try Curling! It’s like skating, but in your shoes, while you hold a rock (called a “stone”). In this game, two teams take turns sliding stones down the sheet of ice, trying to get as close to the center of the target as possible. After you release the stone, your teammate chases it and sweeps the ice (with a special broom) in front of it to change its speed and direction towards the target.

Unlike other popular sports like hockey or football, the etiquette for a curling match is much more refined, with a deep sense of tradition. For example:

  • When playing a game, you are expected to shake your opponent's hand and introduce yourself. 
  • There is no name-calling or remarks about bad shots. 
  • Traditionally, the winning team buys their opponent a drink after the game. 

Places to curl in Chicago

3. Visit the Lake: Lake Michigan

When visiting Chicago during winter, a visit to the Lake Michigan shore is a must. Bundle up in a warm wool winter coat (the Dana winter coat is an excellent weatherproof option) and go for a walk along its sandy beaches. Because the lake is over 53 miles across, you can’t see the other shoreline, giving you the feeling of being in an oceanfront town, despite being in the middle of the continent.

Here are a few activities to enjoy around Lake Michigan

  • The Lakefront Trail: Various entry points along the coast of the city
  • Navy Pier: Free events and activities throughout the year at Navy Pier. 

Things to do in Chicago in the winter: Indoor Attractions

If the cold weather is just too much in the windy city this holiday season, try these indoor attractions and activities: 

4. Art Institute

Located in downtown Chicago is the Art Institute Chicago. They feature current and historical art exhibits and educational programs for people of all ages.

They have several free ticket options for local residents, kids under 14, teenagers, active duty military, LINK and WIC Cardholders, Illinois teachers, Kids Museum Passport holders, and other university and corporate partners. 


Address: The Art Institute has two entrances:

  • Michigan Avenue Entrance: 111 South Michigan Avenue, Chicago, IL 60603
  • Modern Wing Entrance: 159 East Monroe Street, Chicago, IL 60603

5. The Magnificent Mile

Located over 13 blocks of North Michigan Ave, the Magnificent Mile hosts over 460 stores, 275 restaurants, 60 hotels and unique adventures and entertainment around every corner. There is something for everyone as you visit all the fantastic shops and attractions this route. 

In this fashionable district, a popular Mia Melon jacket will ensure you are warm and stylish. If you’re visiting the city, no one will be the wiser, rather than making you stand out as a tourist, your warm wool coat will help you fit right in.

Address: This entertainment and shopping zone extends north to North Avenue, south to Randolph Street, east to Lake Michigan, and west to the Chicago River.

6. Hancock Building

The stunning 360 degree skyline views of the city fascinate tourists and Chicago residents alike. The Hancock Building is located in the famous Magnificent Mile district and boasts the fastest elevator in North America, taking you up 1,000 feet in 40 seconds. It’s a great place to observe winter in Chicago or grab a happy hour drink at Bar 94 while enjoying the views.

Address: Catch the elevator at 875 North Michigan Ave

7. Goodman Theatre 

Grab a warm and elegant winter coat (the Lexi 2 waterproof wool coat is perfect for an evening at the theatre) and catch a show at the Goodman Theatre. This venue has two separate theatres, a 350-seat courtyard theatre and its 856-seat main theatre. 

Address: 170 N Dearborn Street, Chicago, IL 60601

Things to do in Chicago in the winter: Family-friendly

If you’re looking for family-friendly Chicago winter activities to entertain your children, here are some of our favourites:

8. Lincoln Park Zoo

What kid doesn’t love to run around a zoo and check out the animals? The Lincoln Park Zoo in Chicago is no exception! 

Check out the Zoo Lights event and enjoy music, entertainment, and lights. They have several free admission days, and you can check out their website to plan ahead and take advantage of this deal. Not only is this outing fun and whimsical, but it helps support the zoo; all donations and admission fees help support the animals’ care. 

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

9. Shedd Aquarium

Kids love to get up close and personal with sea life, and you can enjoy them together at the Shedd Aquarium. Check out their calendar before you go to see if they have any special events or winter fun planned during your visit.

Address: 1200 S Lake Shore Drive, Chicago, IL 60605

10. Cloud Gate

Millennium Park features one of the best attractions in Chicago: Cloud Gate. This 110-ton art piece looks like a giant silver kidney bean and reflects the Chicago skyline. Your kids will love running around the plaza and looking at their reflection in this giant bean!

Address: 201 E Randolph St, Chicago, IL 60602

Things to do in Chicago in the winter: For the holidays

11. Enjoy holiday music

Winter months wouldn’t be complete without Christmas music filling the air. Whether you’re hosting friends and family at home for dinner, driving around town, or listening to music on your phone, 93.9 Lite FM has turned into Chicago’s Christmas station through the holidays. 

You can listen to 93.9 Lite FM through your radio or the iHeart radio app. You can also get your fix of holiday music at any local festival, too! 

12. Visit holiday markets and festivals

Take in the sights, sounds, smells, and tastes of The Christkindlmarket, authentic, fresh air German Christmas Markets in Chicago, during your winter visit to the windy city. The markets are free to enter and have various events, foods, and activities to indulge in. It’s like being transported to a winter wonderland!

Because these are open-air events, bundle up in a warm, weatherproof jacket to keep you toasty and stylish as you browse the vendors and take in the atmosphere. The Mia Melon Hailey Women’s insulated coat, with its high collar and removable hood, would fit in with the winter market vibe.


  • Daley Plaza, 50 W Washington St, Chicago, IL 60602
  • Gallagher Way, 3635 N Clark St, Chicago, IL 60613

13. Viewing Holiday Lights

There are many places to enjoy holiday light displays in Chicago this year. A not-to-be-missed display is the large Christmas tree at Millennium Park (near Washington st and Michigan Avenue). Weather permitting, you can skate around a traditional skating rink in the same park while enjoying the nearby lit trees. 

Address: Millennium Park Tree - 55 N Michigan Ave, Chicago

Things to do in Chicago in the winter: Food and drink

14. Hot Chocolate

What’s the best remedy for chilly weather in Chicago? Hot chocolate! While out enjoying winter activities in Chicago, bring along a steamy cup of hot cocoa from these favorite spots in the city:  

  • Bombobar - Serving up hot chocolate treats that are adorned with some tasty, Instagram-worthy toppings. 
  • XO Marshmallow - This cafe specializes in gourmet, homemade marshmallows for your drink, perfect for your holiday hot cocoa.
  • Ghirardelli Ice Cream & Chocolate Shop - Try their seasonal flavors including peppermint.

15. Deep-Dish Pizza

It doesn’t matter if you’re enjoying a Chicago summer or Chicago winter, deep-dish pizza must be on your menu. On a cold, snowy day, pop into one of the many Pizzerias in the city to enjoy a warm, melty deep-dish pizza. What makes these pizzas different? They’re cooked in a seasoned cast iron pan, the dough is pressed to the sides of the pan, toppings are layered in the middle, and it’s baked for 40 minutes. 

Fun Fact: The city was founded in 1833, but it wasn’t until 1943 that Chicago pizza was first served. 

Where can you dish up a slice of good pizza in Chicago? Here are 16 of the best deep dish pizza joints in town (as ranked by Timeout.com).

Prepare for winter in Chicago

Whether you’re a resident of Chicago, or planning a winter visit, when you’re properly prepared, Chicago winters can dazzle you. Before heading out the cold, consider these quick tips:

Is Chicago really the windiest city?

Chicago is known for being really windy. While many lovingly call it the “Windy City,” it doesn’t claim to be the windiest city. Boston, New York, and San Francisco frequently record higher wind speeds, but only a few miles faster, on average.

While it may not officially be the windiest city, you’ll want to prepare for the wind and weather when you’re making plans in Chi-town during winter.

What should I wear in Chicago in January?

Chicago weather in the winter isn’t exactly meant for shorts and tank tops. It’s not uncommon to experience snowy days, heavy rainfall, and strong winds in this great city. When it comes to your outerwear, your best bet is to choose a wool winter coat that is both warming and can provide some protection against the wind and rain. 

Look for a coat with durable water repellency so rain will bead and slide off, rather than penetrating the fibers, and sitting next to your skin, making you cold. For extra warmth, a thermal membrane layer helps the jacket be windproof, waterproof, and breathable while deflecting heat back towards your body, a feature you’ll want in the crisp winter air in Chicago.

Stay warm, dry, and stylish in Chicago this winter

Mia Melon outerwear was made for crisp and wet climates like Chicago in the winter. Our jackets are not only stylish but will keep you warm while you’re out exploring all the wonders this beautiful city has to offer. 

Shop Mia Melon weatherproof wool coats