Chicago is absolutely magical at Christmas time, with festive decor festooning the Magnificent Mile, holiday performances on seemingly every corner, and some very special traditions that are unique to the Windy City. I grew up in Chicago—and still go back most Christmases—and, accordingly, have spent a few decades packing in as many holiday traditions as possible.
Here are 11 fun things to do during Christmas in Chicago, from a born and bred local.
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Things to do during Christmas in Chicago
1. Eat around the Great Tree at the Walnut Room
One of the most beloved traditions during Christmas in Chicago is dining at the Walnut Room, a historic restaurant on the 7th floor of Macy’s on State Street. Every holiday season, a MASSIVE and elaborately decorated 45 foot Christmas tree is installed in the middle of the dining room, a tradition that dates all the way back to 1907.
This department store, formerly called Marshall Field’s, is an important part of Chicago history. From its initial opening in the 1860s to 2005 (when Macy’s purchased the chain), the flagship store, anchored in the heart of the Magnificent Mile, helped cement Chicago as an important commercial hub and had lasting impacts on American culture more broadly (fun fact—the phrase “Give the lady what she wants” originated from Marshall Field’s pioneering approach to customer service!).
Over the years, it’s become many Chicagoans’ tradition (including my family’s!) to head to the Walnut Room every Christmas. In fact, my family actually woke up every Christmas Eve at 5 AM, just so we could be the first ones in line there!
Under the ownership of Marshall Field’s, the Walnut Room around the holidays was ABSOLUTELY magical, with themed decorations on the tree (my favorite year was Harry Potter themed) and even Christmas characters that wandered around and interacted with guests.
I may just be slightly salty about corporate takeovers, but, in my opinion, the Walnut Room has definitely lost a bit of its charm since Macy’s took it over. But it still remains an integral part of Christmas in Chicago!
Reservations for the holiday season typically open up on October 1 at 9 AM and pretty much instantaneously book up. However, walk-ups are still accepted—just be prepared to wait for quite a while!
Pssst… while you’re visiting Macy's, be sure to pick up a box of Frango mints, a type of chocolate mints that used to be produced by Marshall Field’s and are a classic holiday gift in Chicago.
2. Enjoy the decorated windows at Macy’s
While you’re at Macy’s, it’s worth perusing the store’s windows along State and Washington Streets, which are decorated with animated holiday displays that usually honor the history of Marshall Field’s and Chicago.
Like the Walnut Room, the window decorations just haven’t been the same since Macy’s took it over, but they’re still fun to check out, with scenes like elves working at a Frango chocolate factory or trees decorated with the store’s iconic Great Clock.
And be sure to look up! Macy’s has retained Marshall Field’s tradition of hanging 42 enormous heralding trumpets above the store’s State Street entrance.
3. Catch the Christmas double feature at the Music Box’s holiday singalong
I hate to play favorites, especially when it comes to Christmas, but my FAVORITE annual holiday tradition in Chicago is to catch a showing of White Christmas and It’s a Wonderful Life at the historic Music Box Theater.
Around the holidays, the theater will play the two movies back to back, with a Christmas sing-a-long, accompanied by an organ and led by Santa himself, serving as intermission between the films.
There’s hot cocoa and mulled wine, served by the concession stand, and there’s always some kind of audience participation, from themed outfits to throwing cotton balls during White Christmas‘ “Snow” song.
It’s seriously cozy and a little quirky—just like Chicago!
Again, this is a super popular tradition with families and friends going year-after-year. Accordingly, I’d strongly recommend purchasing your tickets ahead of time, because the shows sell out well in advance.
3. Caroling in Millenium Park
Every Friday in December, local choirs offer Holiday Singalong performances in front of the iconic Cloud Gate sculpture (i.e., “The Bean”) in Millenium Park. True to its name, you’re encouraged to sing along, with songbooks provided to the onlookers.
It’s totally free, so it’s fun to pop by for at least a few songs and take in the surrounding Chicago skyline, all lit up with red and green lights.
I also love how inclusive the event is—there are usually songs from a variety of faith traditions, as well as ASL interpreters and large print songbooks available.
Pssst… while you’re here, don’t miss Chicago’s official Christmas tree, which is a MASSIVE (up to 80 feet tall!) real tree! The official tree is selected each year through a public nomination and selection process and must be from no further than 100 miles from the Chicago Loop and at least 45 feet tall.
4. Ice skating in Millenium Park and Maggie Daley Park
Another popular Christmas tradition around Millenium Park is iceskating.
There are actually two places to ice skate here—the McCormick Tribune Ice Rink, right below Cloud Gate or the Ice Skating Ribbon, a quarter mile long path that winds through Maggie Daley Park, which sits directly to the east of Millenium Park.
Each of these options have their benefits.
The McCormick Tribune Ice Rink has a kind of nostalgic, ice-skating-at-Rockefeller-Center vibe, especially with its location near the Bean. Plus, there’s actually free ice skating lessons provided here (pre-registration encouraged)!
On the other hand, the Ice Skating Ribbon feels a bit more modern and adventurous, offering constantly changing perspectives of Chicago’s skyline.
5. Explore Christmas around the World at the Griffin Museum of Science and Industry
Remember how I said that, every Christmas Eve, my family would wake up at 5 AM to get breakfast at the Walnut Room? Well, immediately after that, we’d always head straight over to the Museum of Science and Industry to check out Christmas around the World.
Christmas Around the World and Holidays of Light is an annual exhibit at the Museum of Science and Industry (recently renamed the Griffin Museum of Science and Industry), with over 50 trees decorated to represent how Christmas is celebrated in various countries. There are also separate displays to highlight winter holidays in different cultures, like Hanukkah, Kwanzaa, and Diwali. The tradition dates all the way back to 1942 to represent global unity after World War II.
On weekends, there’s also usually cultural dance or singing performances and, sometimes, pop-up stalls selling handmade goods and holiday treats.
Besides Christmas Around the World, you can literally spend all day exploring the MSI. Even though I’ve been there literally dozens of times, I ALWAYS make sure to stop at silent film star, Colleen Moore’s enormous doll house, called the Fairy Castle; the U-505 submarine (which is the only German U-boat on American soil!); and the Henry Crown Space Center, which has actual spacecrafts!
You can get your tickets here.
6. Enjoy the annual poinsettia show at the Garfield Park Conservatory
Regardless of what time of year I visit Chicago, I always make a point to stop by the Garfield Park Conservatory, one of the largest greenhouse conservatories in the United States.
Dating back to the early 20th century, the steel and glass conservatory has seven different rooms that span two acres, with thousands of different plant species, artfully designed with water and stone elements and educational signage.
Each Christmas, they have a winter flower show, with hundreds of poinsettias, in dozens of different colors, and fir trees, decorated with twinkling fairy lights.
If you’re looking to get out of the winter chill for a bit, it’s the perfect way to have a teeny bit of a tropical escape. Plus, it’s quite affordable—free for Chicago residents and just $10 per adult non-resident.
7. Shop at the Christkindlmarket
The Christkindlmarket, a German-style Christmas market, has become one of the most popular things to do during Christmas in Chicago—and has become so iconic that it was recently featured in a Hallmark Channel holiday movie!
The original Christkindlmarket, in Daley Plaza, has over 50 stalls, selling everything that you’d imagine a German market would—mulled wine, Lebkuchenherzen (those giant gingerbread hearts), handmade ornaments and toys, bratwurst, and more. Plus, like actual Christmas markets in Europe, there’s an annual keepsake mug, whose design changes from year to year, that you can either buy empty or full of gluhwein, hot cocoa, or chai.
Chicagoans and visitors alike flock to this market, so if you put this on your Christmas itinerary, I’d strongly recommend coming as soon as the market opens to avoid massive, shoulder-to-shoulder crowds.
The Christkindlmarket has become so wildly popular that it has actually spun off two more (albeit much smaller) locations—one in Wrigleyville (not too terribly far from the Music Box Theater!), as well as in the northern Chicagoland suburb, Aurora, of Wayne’s World fame.
8. Hit a pop-up Christmas bar
Chicagoans LOVE a good theme bar and the city is absolutely filthy with Christmas (and Hanukkah!) pop-up bars around the holidays. Expect lots of twinkling lights, kitschy decor, and overpriced cocktails in festive glassware.
There are dozens of different pop-up bars that change from year to year, but here are a few that have been around a while:
- Santa Baby Bar
- Elfed Up
- Rudolph’s Bar
- Frosty’s (notoriously VERY packed, with the early 20s crowd!)
If cocktail bars aren’t your scene, there are also restaurants that take Christmas decorations to the next level.
For example, whenever my husband and I are in Chicago for the holidays, we stop at Homeslice or Happy Campers, which are both trendy pizzerias that become bedazzled with thousands of twinkling lights every Christmas.
Butch McGuire’s, a neighborhood bar and restaurant, is another local favorite, which has over-the-top decorations, including a toy train that loops around the top of the bar.
9. Ride the Santa car on the El
One of the most magical features of Chicago, regardless of the time of year, is the Chicago Transit Authority elevated train (colloquially referred to as the “El”), which offers an affordable and easy way to get around most of the city.
From late November to late December, there are holiday El trains running on every line that are bedecked with twinkling Christmas lights and festive decorations (even the seat cushions are switched out in favor of ones with snowmen and reindeer on them). You can even get your photo taken with Santa and his “El”ves.
I’ve attempted to catch a holiday El train no less than five times and have somehow always missed it, but if you’re better at being on time for public transit than me, you can check out the schedule here.
10. See a Christmas-themed performance
Chicago is renowned as a cultural hotspot, from its famed improv scene to higher brow performances, like the opera, ballet, and symphony.
There are some very classic Christmas performances that you can catch every year in Chicago, like The Nutcracker at the Joffrey Ballet or A Christmas Carol at The Goodman Theater.
However, there are also TONS of alternative kinds of performances to enjoy.
During one of Justin’s and my most memorable Christmases in Chicago, we saw a holiday burlesque show at a bar, which included a performance of a dancer literally doing cartwheels on top of people’s tables and shooting marshmallows from her bow to Darlene Love’s “Marshmallow World” (quite the show!). And, last year at Christmas, we saw a hysterical musical at the Annoyance Theater, which was a queer take on A Christmas Carol, all about saving a gay bathhouse from being destroyed by corporate greed.
So, while the ballet and classical theater in Chicago are great, I’d suggest taking a look at some other types of holiday performances as well, like:
- The iconic Second City improv theater always has tons of Christmas themed shows around the holidays
- The hilariously and aptly named The Buttcracker is an annual festive burlesque show, parodying the popular holiday ballet, and
- It’s a Wonderful Life LIVE is a theatrical performance of the beloved holiday classic, styled as a 1940s radio broadcast complete with live sound effects and a pre-show Christmas singalong.
11. Drink some glögg at Simon’s Tavern
Unlike the Christmassy bars recommended above, you won’t find any over-the-top holiday decorations at Simon’s Tavern, a proper dive bar that kind of feels like hanging out in your uncle’s living room (in the best way possible).
While we’re generally big fans of dive bars, glögg, a type of Scandinavian mulled wine, is the reason we’d recommend coming to Simon’s around the holidays.
The tavern dates back to 1934, when it was opened by a Swedish immigrant in Andersonville, a historically Swedish neighborhood. While the introduction of glögg here is a bit more recent, Chicagoans (including myself!) have been coming to this bar for over three decades to enjoy the sweet and boozy Scandinavian drink, which is made with port wine, raisins, cardamom, orange peel, almonds, and brandy, and served with a gingersnap cookie on top.
Stop at an ATM first, though, as Simon’s is cash only!
There you have it—the best things to do to celebrate Christmas in Chicago, from a born and bred Windy City kid. Do you have any questions about visiting Chicago around the holidays? Let me know in the questions below!
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