Looking for the top things to do in Chicago during Christmas?  This is the guide for you! 

Chicago is known for its dazzling holiday festivities every year, making Christmas one of the most popular times of the year to visit.

I visit Downtown Chicago during Christmas every year and have created a guide of my personal favorites and expert recommendations. 

From giant events that kick off the season like the annual tree lighting at Millennium Park or more laidback activities like enjoying some holiday rooftop views, being in Chicago during the Christmas season is incredible.

My favorite Christmas activities include holiday rooftops, hot cocoa flights, Christkindl Market, and weekend fireworks. 

There are Christmas activities for every budget in Chicago ensuring you can enjoy the magic of Chicago’s holiday season! 

10 Chicago Christmas Activities

1. Holiday Rooftop

Rooftops in Chicago are one of my favorite ways to experience the city’s beauty. The vantage point is like no other, and visiting during Christmas is one of the best times to go.

My favorite Holiday Rooftop is Rudolph’s Rooftop at London House.  The view is like no other, and the Rudolph seasonal display features tons of photo opps like a giant, red sled, a red telephone booth, and igloos for rent. 

The igloos are very expensive but might be worth it if you are splitting with a large group of friends. 

No reservation is needed to visit the rooftop itself. 

2. Ice Skating at Millennium Park or Daley Plaza

Ice Skating at Millennium Park or Daley Plaza are two of the best activities to do during Christmas in Chicago! 

Reserving timed entry tickets is required in advance.  Entry is free if you bring your own ice skates.

Tip: The Maggie Daley Skating Ribbon is conveniently opened on Christmas Day in Chicago. 

3. Hot Cocoa Flights at JoJo’s Winter Wonderland

Hot Cocoa flights at JoJo’s is one of my favorite ways to kick off Christmas in Chicago!  One flight features four different hot cocoa flavors: double chocolate, peppermint, salted caramel, and marshmallow. 

The cups are super tiny and cost $18 per flight.  I think it’s worth it to split with friends and for the festive atmosphere of the Winter Wonderland pop-up. 

JoJo’s features other seasonal pop-ups throughout the year like its pumpkin patch during October in Chicago. 

Tip: Reservations are not required but I highly recommend making one in advance.  This will spare you a long wait time during this busy time of year. 

4. Christmas Tree at Millennium Park

The giant Christmas Tree in Millennium Park is a beloved favorite among Chicagoans and tourists visiting for the season. 

The annual tree lighting ceremony took place on November 15th, 2024.  Visitors can visit it until January 1st throughout the holiday season. 

This is a great urban spot for family Christmas photos with the city skyline as a backdrop! 

5. Themed Holiday Pop-Ups

There are limitless themed Christmas pop-ups throughout the city.  One of the newest pop-ups gaining attention this year is the Mariah Cary pop-up at Virgin Hotels. 

Entrance tickets cost $20 for general admission.  Timed entrance tickets in advance are required. 

Other holiday pop-up events at bars and restaurants in Chicago in 2024 include:

• Jack Frost Christmas Pop-Up
• 8 Crazy Nights at Graystone Tavern
• Tinseltown at Pink Squirrel

6. Christkindl Market

Christkindl Market is one of Chicago’s most beloved holiday traditions. 

The annual market kicks off Christmas in Chicago followed by the tree lighting at Millennium Park every year. Its prime location at Daley Plaza makes it central to other Christmas activities like ice skating.

I love to wander the market, purchase an annual souvenir mug (I have way too many!), and buy a tasty hot cocoa. There are plenty of artisan shops selling handmade items and international souvenirs.

The market’s opening in November also makes it one of the best things to do during Thanksgiving weekend in Chicago. 

7. State Street

State Street is illuminated by beautiful twinkling lights during the holiday season in Chicago. 

Visitors love to see the annual Macy’s holiday window displays that change each year. 

Another great Christmas activity at Macy’s on State Street is to make brunch or dinner reservations in the infamous Walnut Room. 

8. Saturday Fireworks at Navy Pier

Navy Pier features annual fireworks starting on November 30th and concluding on December 31st.

The fireworks show lasts for approximately 15 minutes and is a stunning display of lights choreographed to holiday music.

The official fireworks start time is 9 PM on Saturday evenings, offering a perfect way to cap off a winter night in the city.

The recommended viewing location is on Navy Pier’s South Dock. Check the Navy Pier website for additional information or cancellations.

The fireworks show is one of the best free things to do in Chicago in the winter!

Tip: You can catch fireworks to kick off the holiday season on Michigan Avenue during the annual Magnificent Mile Light Festival. 

In 2024, the event took place on Saturday, November 23rd. 

9. Winter Wonderland at Gallagher Way

Gallagher Way refers to the green space located directly outside of Wrigley Field in Chicago’s Lakeview neighborhood.  No, the Chicago Cubs are not playing during the winter season!

However, you can get your fill of holiday activities from bumper cars on an ice skating rink, a huge Christmas tree, holiday lights, treats for purchase, and more. 

Entrance to the Winter Wonderland is free.

10. Music Box Theatre Christmas Classics

The Music Box Theater is one of Chicago’s oldest movie theaters and features original Christmas Classic films throughout December.   

The annual Christmas movie screenings include ELF, It’s a Wonderful Life, Home Alone, White Christmas, and more! 

Check the Music Box Theatre website for up-to-date show times and ticket prices. 

Conclusion

Chicago offers countless festive activities for first-time visitors during the holiday season.

From exploring the Christkindl Market and admiring Macy’s holiday window displays to enjoying fireworks at Navy Pier and skating at Gallagher Way, there’s plenty to celebrate.

Don’t forget to watch classic holiday films at the Music Box Theater for a cozy seasonal experience.

These activities showcase the magic of Christmas in Chicago.