Best Things To Do In Chicago For The Holidays

I’ve had the pleasure of growing up in the south suburbs of Chicago, and with that comes memories of holiday activities in the city that I treasure. No matter if you’ve been to the city countless times like me or have never been at all, I find that the most fun can be had during the holiday season. Here are my top picks for the best things to do this holiday season: 


Christkindlmarket Chicago

The market runs from November 15 to December 24, leaving you a good chunk of time to walk around and explore the various vendors. The outdoor market, which is inspired by those in Germany, showcases several food booths as well as lots of holiday-themes merchandise. On select days, the market also features choirs and other musical performances, which just adds to the holiday magic. This is definitely something I plan on visiting this year!

Ice Skating in Millenium Park 

Although I myself have never gone ice skating, I feel like this is a must-have on a holiday activities list. Held in the McCormick Tribune Ice Rink in Millenium Park, you can skate under the picturesque city skyline, and you might even catch a glimpse of the Chicago Christmas Tree as you skate around the rink. Although it costs $13-$15 to rent some skates, the actual admission is free, which means this is a cheaper activity to do on a date or with a big group of friends. There are also free skating lessons at select times on Fridays and Saturdays if you’re like me and don’t know the first thing about being out on the ice! 

Holiday Lights Tour with Chicago Trolley

This ticketed experience through the Chicago Trolley & Double Decker Co. is the perfect way to explore some of the most popular spots in the city while also experiencing the holiday cheer that looking at all of the lights brings. According to the website, each rider also gets a complimentary bag of Hot Cocoa CaramelCrisp® from Garrett Popcorn, which in my mind, is just the icing on top of the cake for a fun activity (because, as anyone who has ever had Garrett Popcorn knows, it is one of the best treats ever!). 

Christmas Around the World at the Museum of Science and Industry 

I remember loving this as a kid! The museum sets up a four-story tall Christmas tree, which is then surrounded by 50 other trees depicting holiday traditions from countries around the world. There are also featured performances on the weekends showcasing various songs and dances representing different cultures. There are also opportunities to make your own ornament, and is a super fun experience while also visiting one of the city’s museums (it’s like you’re getting two things in one!). 

Lightscape at Chicago Botanic Garden

Running from November 22 to January 5, this mile-long illuminated trail includes grand light displays and synchronized music is sure to dazzle. Although it is ticketed (a breakdown of tickets can be found on their official website), it is a cool experience to have (if only to get a few cute pictures to post on your Instagram). 

Lunch in Macy’s Walnut Room

I am really hoping I get around to visiting the Walnut Room this year, because it truly is very special. The Walnut Room (which is the seventh-floor restaurant inside of Macy’s) houses a Christmas tree that is 45 feet tall. It’s been a tradition for many Chicagoans and their families since 1905, so it’s definitely something to keep in the back of your mind when you’re in the city!

The Nutcracker (The Joffrey Ballet Chicago)

Although I know the ballet isn’t everyone’s cup of tea, I felt like I absolutely had to include this Christmas classic. I’ve performed the show two times (although not through the Joffrey, I wasn’t that skilled!), and it truly is a magical and heartwarming story. The Joffrey actually debuted a new version of the show in 2016, set in Chicago against the backdrop of the 1893 World’s Columbian Exposition, which only elevates the experience of seeing it performed while you’re in the city. 

Chicago Helicopter Tour With Holiday Lights 

Okay, this one may be a little dramatic, but I feel like it was so spectacular I had to include it on my list. I will be the first to say that this is not your typical holiday activity, but this helicopter tour is a pretty neat way to explore the entire city without walking an inch. The pilot-led flight departing from the Downtown Chicago heliport is designed to show off the great spectacle that is the city of Chicago. 

There are dozens of other things I could’ve included in this list. Spending the holidays in a big city such as Chicago only leads itself to several opportunities to make fun memories, and even start new traditions. And you may be having so much fun that you forget about the frigid cold and lake-effect snow that, although annoying, only make Chicago holidays more memorable.