18 Fun Things to Do in Chicago in December

Are you looking for a festive holiday destination to celebrate this year? Then Chicago is the place for you! The Windy City goes all out for the holidays, making it a great place to enjoy the season with lights, hot cocoa galore, Santas, ice skating, and more.

Chicago is a great place to visit in December. It’s a white winter wonderland this time of year, and there are so many things to do in Chicago around Christmas! Layer up for the cold, and enjoy the snow and holiday magic that make Chicago a great place to celebrate the holiday season.

If you’ve never been to Chicago, but are planning to go for the holidays, you’ll definitely want to check out some of the most popular city attractions as well. Check out the must-do sights and activities in Chicago for first-timers!

As you plan your holiday trip to Chicago, remember these tips to help you make the most of your city trip!

1. Christkindl Market

You don’t have to travel all the way to Europe to enjoy an authentic Christmas market! Chicago is home to Christkindl Market; with multiple locations, you can enjoy the holiday decorations, and different vendors, go shopping, and sip on mulled wine to complete the experience!

2. Ice Skating at Maggie Daley Park

There are multiple locations to enjoy a round of outdoor ice skating in Chicago, the two best being Wrigley Field (home of the Chicago Cubs) and Maggie Daley Park. With a unique “ribbon” shaped rink, it feels like you are ice skating on a frozen river through a beautiful winter wonderland at Maggie Daley Park!

3. Sip on the Best Hot Chocolate

Did you know you can get amazing hot chocolate in Chicago? Grab a cup of hot cocoa to add a festive touch to your holiday trip! It's the best way to keep warm while exploring Chicago in December.

Three of the best places to get hot chocolate in Chicago, both traditional and unique flavors, are:

4. Macy’s Windows

There's no shortage of Christmas lights and fun decorations in Chicago, especially downtown. Stop by Macy’s in downtown for a traditional holiday activity in Chicago! The windows all display their own holiday scene with extravagant decorations, music, and more. You can even take your kids to meet Santa!

5. Giant Christmas Tree in Millennium Park

Home of the giant Christmas Tree, Millennium Park is another fun place to visit in December in Chicago. With a 40+ foot tree, completely decorated with lights, this is a Christmas sight to see! Even if you don’t celebrate the holiday, this tree will put you in a cheery, festive mood!

6. Afternoon Tea at The Drake

For a truly magical dining experience, make a reservation at The Drake hotel for an afternoon holiday tea. Suit up in your best holiday dress attire and enjoy an array of delicious pastries, teas, sandwiches, and more. Afternoon tea is a fun, yummy way to enjoy the holidays. If you’ve never been to one before, it’s such a lovely experience!

7. Shop & Walk the Magnificent Mile

You can’t visit Chicago without walking down the Magnificent Mile, or "Mag Mile" on Michigan Avenue. With shops upon shops and lights all down the street, this is a great place to go window shopping, or maybe even find a gift or two! There is a store for everyone, from Disney to Anthropologie, and more!

8. Drink at a Holiday Bar

There are some killer pop-up holiday bars in Chicago! If you enjoy a good cocktail, especially a holiday-themed one, head to Wrigleyville, and walk around the Wrigley Field area. There are several holiday pop-up bars in this area. For the ultimate holiday spirit, check out Mordecai and Smoke Daddy.

9. Holiday Movies at Music Box Theater

Go for a calmer holiday activity in Chicago and head to the Music Box Theater! This elegant 1920s theater is a wonderful place to visit any time of year, but visit in December and you’ll be able to catch a holiday movie classic or two. Don't forget the popcorn!

The Music Box is located off the Southport brown line stop (train line) which is super festive in December; go early and walk around the area, or stay after your movie for a great dinner.

10. Take a Ride on the Holiday Train

In true Chicago style, use the CTA and wait for the fully decorated holiday train to pass through the station. If you’ve never seen a fully decked-out holiday train, then you need to see this at least once! It’s fun for everybody, and you’ll most likely catch Santa waving at you! Check the holiday train schedule here.

11. Get Cozy in a Coffee Shop

Chicago is full of amazing local coffee shops, many of which roast their own beans. After some city exploring, cozy up in one of the best coffee shops in Chicago and sip on a delicious drink.

While not a local place, the Chicago Roastery - Starbucks Reserve is a fun experience around Christmas. With five floors, you can find much more than your typical Starbucks coffee here. They also offer a full food menu, cocktails, coffee tastings, and more. Plus, the lights and decorations are so fun to admire here!

12. Museum of Science and Industry: Trees Around the World

Chicago is home to a plethora of fantastic museums, from history to art to science. If you only have time for one on your Chicago holiday trip, make sure you visit the Museum of Science and Industry (MSI).

They have the "Christmas Around the World and Holidays of Light" exhibit which showcases more than 50 trees decorated to highlight different countries and cultures around the world! Check out the Kenya tree below.

13. Lincoln Park Zoo Lights

There's nothing quite like walking around a zoo at night while it's decorated in festive Christmas lights. Experience this holiday activity at the Lincoln Park Zoo Lights throughout Chicago's winter. Admission is free on Mondays and $7 the rest of the week. Fun for the family or the adults! Check when the adult-only night is and plan your visit.

14. Lakefront Trail Winter Wonderland

Bundle up and enjoy this traditional Chicago activity in the snow. The Chicago Lakefront Trail is a popular walking and biking trail that stretches along the Chicago coast of Lake Michigan. This trail offers some of the best skyline views of Chicago, and it's gorgeous when covered in snow. Remember your winter coat though!

15. The Nutcracker by Joffrey Ballet

Dress in your best festive outfit and enjoy this classic holiday show. The Nutcracker is a beautiful ballet, and every winter the Joffrey Ballet performs it live in Chicago. Plan this activity in advance and buy tickets for the Nutcracker when you plan your Chicago holiday trip.

16. Participate in the Santa Hustle 5K

Want to get active and help a charity? Sign up for the Santa Hustle 5K! This event takes place every December in downtown Chicago. This is your chance to run around the Windy City while helping a nonprofit raise money.

17. Go See "A Christmas Carol"

Another Holiday classic, A Christmas Carol, is performed live every December at Chicago's Goodman Theater. Buy tickets in advance and enjoy this holiday show for a truly festive time. Is it even Christmas time until you've seen this holiday favorite?

18. Enjoy Chicago Deep Dish Pizza

You can't visit Chicago without eating a deep dish pizza! This traditional Chicago treat is fresh, filling, and super cheesy. Head to a local Lou Malnati's or Giordano's for the best Chicago deep dish pizza; it's the perfect hot meal to have on a winter day.

Read Also: 15 Fun Restaurants in Chicago

Choosing Accommodations

Finding the right accommodation for any trip is essential. A hotel or Airbnb can really make or break a trip. Browse the best places to stay in Chicago, from budget options to great locations. Make this adventure to Chicago in December a memorable one!

What to Wear in December

Chicago is cold and snowy in December, but that doesn't mean you can't have fun and still explore the city! As long as you know what to wear in Chicago in winter, you'll stay warm and comfortable and fall in love with this city winter wonderland.

Wear warm layers and bring a winter coat, hat, gloves, and scarf to comfortably explore Chicago in December.

Tips for Navigating the Winter Weather

Driving in Chicago without snow is stressful enough. Do yourself a favor and opt to use the CTA, or public transportation, to get around Chicago in the winter. You'll save money and you won't have to worry about traffic and snow.

Is it too cold to go to Chicago in December?

December is a great time to visit Chicago. Yes, it is cold and snowy, but as long as you dress for the cold, you'll be able to explore the city in its most festive state.

The holiday season is in full swing this time of year, and the city is a snow-covered wonderland. There are decorations and displays all around the city, as well as other fun holiday activities like ice skating and the Christmas market. If you want to plan a festive holiday trip in December, Chicago is the place to go!

Can you walk in Chicago in winter?

Chicago is always prepared for snow. Roads and sidewalks will be plowed and salted; snow doesn't deter Chicagoans from living their best lives. You can still walk around in Chicago in winter, but you can also utilize the CTA (public transportation) for a cheap and warm mode of transportation.

What is the best winter month to visit Chicago?

December is the best winter month to visit Chicago. This month brings the most festive activities; the city is bright with Christmas lights and cheery from all the holiday spirit. December is also cold enough to experience a snow-covered Chicago, but it's not as cold as January or February.

These are the best things to do in Chicago around Christmas! You’ll be able to find Santas to take photos with, carols to sing along to, and tons of goodies to buy. Chicago is also home to a killer dining scene, so make sure you eat plenty while in town.

Visiting Chicago in December is a great idea. Knowing what to pack, where to stay, and the best things to do to celebrate the holidays in Chicago will make your city trip the best possible! Get ready to bundle up, enjoy the beautiful snow, and get in the holiday spirit.

With lights, decorations, snow, food, and music all around, Chicago truly is the ultimate festive winter destination! Plan a holiday trip to the Windy City for a jolly good time. What will you be doing first in Chicago in December?

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