25 Holiday Activities in Chicago

Chicago is a wonderful city for holiday and Christmas activities. This post includes 25 holiday activities in Chicago, from performances, to ice skating, to a gingerbread house decorating party – one for each day of December until Christmas is here.



One of the reasons I love living in a big city is the opportunity to experience and participate in a variety of events and culture. The holiday season is a particularly good time to try new things with family and friends. You can find holiday activities taking place every weekend across the Chicago area. I learned about many new {to me} events while researching this post. With a newly minted one-year-old in my family this year, we will likely only make it to a few things on this list.


1. Visit the Christkindl Market

The Christkindl Market is one of my favorite holiday activities in Chicago, with three locations this year – Daley Plaza, The Park at Wrigley, and Naperville. We visited Daley Plaza two weekends ago when my mom was in town and it was packed with people. I need to go back to pick out a Christmas ornament and enjoy Gluhwein.



2. Lunch at The Walnut Room – Macy’s

The Walnut Room is exceptionally festive during the holiday season, with a huge Christmas tree and holiday decor. The restaurant has been open since 1905 at what was once Marshall Fields {now Macy’s}, located on State Street in the Chicago Loop.



3. Caroling at Cloud Gate

If you’re a Christmas caroler, you can get your sing on every Friday at 6pm at the Cloud Gate in Millennium Park. Click here for more information.


4. Winter WonderFest at Navy Pier

Navy Pier hosts an annual winter carnival at Navy Pier that families with children would love {large crowds aside}. The event is open until January 7. Click here for ticket information.


5. Holiday Flower Show at Lincoln Conservatory

The Conservatory in Lincoln Park is free and holds a holiday flower show event during the holiday season. I haven’t visited this event before but am planning to take C this year. Click here for more information.

6. Christmas Around the World at Museum of Science and Industry

Christmas Around the World is one of my favorite holiday events in the area. The Museum of Science and Industry goes all out with holiday decor, including many Christmas trees decorated in the theme of different countries. I visited twice this year when C was a tiny baby. It’s a very family friendly event.



7. Ice Skating

I’m extremely uncoordinated, but I can take a few slow laps around the ice skating rink as good as anyone! There are many ice skating options in Chicago, including the Maggie Daley Park Skating Ribbon and McCormick Tribune Ice Skating Rink. Click here for more information on indoor and outdoor skating rinks.


8. ZooLights at Lincoln Park Zoo

I always make an annual trip to the free ZooLights exhibit at Lincoln Park Zoo, rain {snow} or shine. I didn’t make it last year since C was only a few weeks ago, but I’m hoping we find ourselves there this year to check out the holiday light displays and festive music.



9. Illumination: Tree Lights at the Morton Arboretum

If the weather holds up in the coming weeks and doesn’t get too chilly, we are planning to take C to see the Tree Lights exhibit with his grandparents at the Morton Arboretum. I have heard it is a beautiful event and very festive. Find more information on tickets here.


10. CTA Holiday Train

We rode the CTA holiday train for a few stops last night and C saw Santa for the first time. I’m sure he was quite confused but he seemed to enjoy the festive lights. Find the holiday train schedule here.


11. The Nutcracker – Joffrey Ballet

There are many performances of The Nutcracker around Chicago, including the Joffrey Ballet. My mom and I went to a performance when she was in town visiting a few years ago and it was unbelievable – absolutely beautiful scenery and music. I would go back in a heartbeat.


12. Wonderland Express at Chicago Botanic Garden

A family-friendly train exhibition through the holidays. Find tickets here.


13. Holiday Flower Show at Garfield Park Conservatory

Garfield Park Conservatory puts together a beautiful holiday flower show with a different theme each year {last year’s theme is pictured below}. Spending time in the heated conservatory is perfect for the winter months, and the Conservatory is free {though donations are greatly appreciated}.


14. Christmas-Themed Pizza at Marie’s Pizza & Liquors

Marie’s Pizza is well-known on the northwest side for its exceptional Christmas decorations and tasty pizza. We haven’t been before but have enjoyed their pizza – I hope we can find a time to take C this year. Check out this article for more information.


15. Holiday Tea

I love going to tea service for lunch or in the afternoon, especially during the holiday season. I have visited the Drake Hotel for their holiday tea {pictured below} but several other hotels and restaurants offer tea service as well. Click here for a list of restaurants that offer high tea service.



16. Home Alone Concert at the Chicago Symphony Orchestra

On December 9 and 10, the Chicago Symphony Orchestra is performing the movie Home Alone, in concert. Click here for more information on tickets.


17. Dance-Along Nutcracker at the Chicago Cultural Center

This weekend {Sunday, December 3} the Chicago Cultural Center is hosting a free nutcracker event with dance lessons and performances. What a neat experience for kids! Find more information here.


18. Gingerbread House Decorating Party – Park Grill at Millennium Park

I have only tried decorating a gingerbread house once, and it was somewhat of a fail. Perhaps doing so in a group setting would be more successful! The Park Grill at Millennium Park is hosting a Gingerbread House Decorating Party on Sunday, December 17. Find tickets here.


19. Art Institute Chicago – Holiday Thorne Rooms

The Art Institute decorates their tiny homes / rooms exhibit with festive holiday decor. I have never visited the Holiday Thorne Rooms, but would love to add it to our event list this year. Can anything be cuter than tiny Christmas trees?


20. Ugly Sweater Party – Park & Field in Logan Square

Time Out Chicago is hosting the first annual Ugly Sweater Party in Logan Square on Thursday, December 7, featuring cocktails, s’mores and board games. Sounds like my kind of holiday event. Click here for more details.


21. Ultimate Holiday Movie Series – Time Out Chicago

Time Out Chicago is hosting the Ultimate Holiday Movie Series at Lagunitas Brewing Company and Baderbrau Tap and Kitchen, showing holiday movies with drinks. Find more information here.


22. The Night Market Before Christmas – Chicago Athletic Association

The Night Before Christmas is a pop-up shopping event on Tuesday, December 12, taking place at the Chicago Athletic Association hotel. The event will also feature local food and drink vendors. Find more information here.


23. A Christmas Carol

A Christmas Carol is an annual performance in Chicago, taking place this year at the Goodman Theatre. Click here for ticket information.


24. Christmas Performances – Broadway in Chicago

Ken Ludwig’s ‘Twas the Night Before Christmas – Emerald City Theatre
Irving Berlin’s White Christmas


25. Run a Holiday Race

My friend S and I have run a few holiday races together over the past few years, including the Rudolph Ramble and Santa Hustle race. The photo below is from an exceptionally mild holiday race where we made the mistake of wearing {wool} Christmas sweaters to the run. Find a list of December races in the Chicago area here.



Interested in more holiday-inspired posts?

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