The Best Holiday Activities in Chicago

Happy Monday. friends! I always love updating this post every year because Chicago is pretty magical during the holiday season. We don’t mess around with our decorations, and the activities don’t stop just because it’s winter (the cold never bothered us anyway ?). If anything, the snow makes it even more special sometimes!

Whether you’re new to Chicago or you’ve lived here a long time, add some of these fun events to your calendar this month. Trust me, they’ll definitely put you in the Christmas spirit! And let me know if you think I missed any of the best holiday activities in Chicago!

Best Holiday Activities in Chicago

1. Christkindlmarket

The Christkindlmarket is one of the most beloved Christmas traditions in Chicago. Even when it’s cold, this outdoor market is packed with people shopping around and hoping to get their hands on a pretzel or mug of hot spiced wine. (YUM!) They also have one up in Wrigleyville at Gallagher Way if you don’t want to go all the way downtown! Adam and I went 2 years ago and it’s so fun to get in the Christmas spirit with Wrigley Field right next to you.

2. Zoo Lights

Going to Zoo Lights is one of my personal favorite holiday activities. It’s pretty magical to walk around Lincoln Park Zoo completely decorated in lights. There’s even holiday music playing wherever you go! Grab your significant other, some friends or your family, take a stroll around, and then grab dinner in Lincoln Park. The perfect evening!

3. Jack Frost Winter Walk

If you went to Jack’s Pumpkin Pop-Up, did you know they do a quick little makeover and turn it into Jack Frost Winter Walk?! They have ice skating, seasonal drinks, photo ops (duh!), bumper cars, and even a Christmas tree farm with trees for sale!

4. Ice Skating

If you go to Millennium Park, there are two ice skating options. The first is a rink right by the bean, which is super fun – especially if you have out of towners with you. If you’re a little more advanced, you could also skate on the Maggie Daley “Ribbon.” The path, which is twice a long as a traditional skating rink, winds through the park and is really pretty when there’s snow on the trees! You can get information about both on this site. (There is also ice skating at the Christkindlmarket in Wrigley!)

5. Visit the big Christmas trees

Every year I love to visit four Christmas trees in the city. The first one is right outside of the John Hancock Building, because that’s where Adam proposed! The second is inside 900 North Michigan because there’s something so fun about Christmas shopping with a huge tree in the middle of the building – it’s the best! My other favorite is just a few blocks away, outside of the Waldorf Astoria Hotel (the first picture in this post!). That hotel is pretty glamorous on it’s own, but a big beautiful Christmas tree makes it even better. And the last is outside of The Wrigley Building, pictured directly above. They just never get old!

6. See A Christmas Carol at The Goodman

Get this. The Goodman Theatre has been performing A Christmas Carol to Chicago audiences for over 40 YEARS. Seriously, how amazing is that?! If you’ve only ever seen movie versions, I’d definitely grab some tickets to the live production. It will give you all the Christmas feels!

7. Walk past Macy’s Windows

If you are a true Chicagoan, these will always be “the Marshall Field’s windows” – but either way, Macy’s still does a beautiful job. And after you check out the themed window displays, head inside to the Walnut Room where they have a 45 foot tree on display! 

8. Christmas Around the World at The Museum of Science and Industry

I’ll be honest, I’ve never done this… but after doing some research, I totally want to now! Christmas Around the World at The Museum of Science and Industry features a four story floor-to-dome Grand Tree – and if that wasn’t enough, there are 50 more trees and displays all around it representing different holiday traditions from cultures all over the world. So cool, right?!

9. Holiday Tea at The Drake

So you wanna be fancy, huh? Then you better go to the Holiday Tea at The Drake. Bring your favorite ladies and sip on French tea and pastries while listening to Christmas Carolers and a harpist!

10. See The Nutcracker

Nobody does The Nutcracker like the The Joffrey Ballet. But last year, they reinvented the classic production with the help of Tony Award winning director, Christopher Wheeldon. It’s been described as “a must see tradition boldly reinvented for a new generation.” Intrigued? Me too!

11. Ride the Holiday Train

I know this requires a little luck… but if the Holiday Train pulls up, your commute just got WAY more fun!

12. Have a drink at a festive bar

Chicago has always gotten into the Christmas spirit – but now more bars are joining in on the fun than ever before! Lottie’s Pub is an old favorite – but if you want something over the top, Santa Baby and Frosty’s Christmas Bar are no joke! Who else wants to try the Yule Mule at Santa Baby this month?!

What are your favorite holiday activities in Chicago?

PS. You might also like my Gift Guides and other holiday content, too!