The autumn-winter transition has begun, and the Midwest’s icy winter is now at our doorstep. More importantly, though, festive time in Chicago is in full swing, and another year is drawing to a close.
Make no mistake: winters can be as beautiful as they are brutal, and despite the chilly weather, plenty is going on. We’ve compiled a list of the best things to do in Chicago in December—activities worthy of stepping outside to brave the Chicago chill and others you can do from the warmth of the indoors.
From light shows to holiday pop-ups, here are our best December-time activities in and around Chicago.
1. Sip Glühwein at Christkindlmarket
Chicago’s German-inspired annual holiday market, considered one of the best holiday markets in the world is one of the most popular Chicago traditions of the holiday season.
Both international and local vendors have flocked to help provide an authentic and atmospheric Christmas experience every year since it first came to the city in 1996. Now, Chicagoans and tourists alike can once again enjoy mulled wine, holiday snacks, and festive music at three different locations in the Chicago area.
Read more about Christkindlmarket in Chicago.
2-3. Enter a world of light, color, and sound at Chicago Botanic Garden’s Lightscape
Chicago’s many light shows are some of our most treasured winter traditions. Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine, providing us with magical multi-sensory holiday experiences, and of them all, Lightscape at Chicago Botanic Garden is one of the most magnificent.
After debuting in 2019, the trail of twinkling lights has been a complete sell-out in its first four seasons. The electrifying event allows visitors to embrace the season’s beauty and immerse themselves in a world of light, color, and sound.
Now running on select dates until January 7, 2024, this year’s Lightscape features both brand-new installations and beloved favorites!
Read more about Lightscape at the Chicago Botanic Garden.
4. Venture to the magical Winterland experience this holiday season
A magical experience is opening at Navy Pier this holiday season! Winterland takes you inside an interactive adventure filled to the brim with Christmas enchantment. The brand-new holiday attraction features high-tech projections and captivating lighting, taking you inside a festive world from November 22, 2024 to January 5, 2025.
At Winterland, you’ll encounter a giant snow globe, a 16-foot-long Polar Express-themed train, frozen icicle walkways, giant Nutcracker soldiers and so much more. Perfect for the entire family, don’t miss out on enjoying this festive experience. – Melissa Maynard
5. Revel in Morton Arboretum’s Illumination: Tree Lights
Voted as the best light display in the Midwest last year, Chicago’s beloved Illumination: Tree Lights at The Morton Arboretum is another sensational light show you’ll want to secure tickets for this month.
Back for its eleventh edition, the popular experience features 19 unique displays accompanied by music soundtracks that together highlight the beauty of trees in winter.
Situated across 50 acres of the nonprofit public garden and outdoor museum Illumination: Tree Lights takes guests snaking through the Arboretum’s majestic landscape along an enchanting one-mile tree-lined walking trail.
Read more about Morton Arboretum’s TreeLights.
6. Head to Lincoln Park Zoo for ZooLights
Making up Chicago’s top trio of light shows, Lincoln Park Zoo’s ZooLights is the third light show to have in your calendar.
The much-loved annual event at Chicago’s beloved zoo features hundreds of larger-than-life 3D LED displays as well as a one-of-a-kind light maze and an enchanted forest offering guests the chance to “meander among butterflies, flowers, mushrooms, and dripping lights with whimsical music and a magical ambiance.”
With many $5 nights and free Mondays, it is one of Chicago’s most affordable and enjoyable holiday experiences.
Read more about ZooLights at Lincoln Park Zoo.
7. Experience “alpine in the city” at Maggie Daley Park
Though ice rinks in Rosemont, Millennium Park, and elsewhere offer wonderful skating experiences, there are none quite like the Maggie Daley Park ice rink.
One of Chicago’s best winter-time activities, the Maggie Daley ice rink offers an “alpine in the city” experience, skating down a quarter-mile rink in the heart of Chicago.
The winding ribbon of ice curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must-do winter activity, and this year you can skate for free at all time slots Monday through Thursday and during the 11 a.m. sessions on Fridays, Saturdays, and Sundays!
Read more about the Maggie Daley Park ice rink.
8-11. Be captivated by a Christmas Candlelight Concert
Candlelight concerts offer another incredible spectacle that can be enjoyed this December. Step into Chicago’s most exquisite spaces to experience some treasured holiday classics.
From holidays concerts to tribute performances, the beloved Candlelight series is bringing talented musicians to perform at venues illuminated with hundreds of candles this season, and dates have been added due to popular demand.
See the full list of candlelight concerts in Chicago.
12-13. Sing your heart out at the Millennium Park Holiday Sing-Along
If all those concerts have you feeling musical, you can celebrate the joy of the holidays with a free classic sing-along in the park! This annual tradition features various choir and ensemble groups in what’s sure to be a show-stopping performance.
There’s nothing better than coming together over the love of music at this time of year! PS: The sing-alongs are taking place on Fridays, December 1, 8, and 15, in Millennium Park’s Wrigley Square.
Read more about the Millennium Park Holiday Sing-Alongs.
14. Enjoy a cozy Sinatra-themed Christmas concert
Taking place at Teatro ZinZanni for one night only, “A Very Sinatra Christmas Special” is making its way to Chicago to spread some holiday cheer. Get ready to kick back with a drink in hand and bathe in a chandelier-lit glow as you enjoy a catalog of festive tunes that Sinatra loved to sing.
The concert features one of Chicago’s best jazz vocalists and will kick off on Tuesday, December 10 at 8 pm. Snag tickets here!
15. Ride the Polar Express
The Polar Express is returning to Chicago for its first full post-pandemic season once again offering Chicagoans the chance to be whisked away on a magical one-hour trip to meet Santa.
Taking place from Sunday, December 3 through to New Year’s Day, Union Station’s Polar Express Train Ride invites passengers to experience the classic children’s story by Chris Van Allsburg firsthand on a real train set to the sounds of the motion picture’s iconic soundtrack.
Read more about the Polar Express here.
16. Catch the CTA Holiday Train
Another one of Chicago’s most cherished Christmas events is the arrival of the CTA Fleet and its journeys around the city.
The Chicago Transit Authority’s train and bus are decorated inside and out with festive decorations and thousands of lights to make them glow as they glide and glimmer around Chicago providing affordable fun for all Chicago families.
Now in its 32nd year of operation, the Allstate CTA Holiday Train and the Allstate CTA Holiday Bus began lighting up Chicago at the end of November and will be whizzing around all eight lines through December 16th.
Read more about the CTA Holiday Train and Holiday Bus schedules.
17-18. See some of history’s most famous artworks completely free
The Art Institute of Chicago, one of the world’s oldest and largest art museums, will offer free admission on Mondays, Thursdays, & Fridays through Friday, December 22nd, 2023.
Since its founding in 1879, the Art Institute of Chicago has flourished into one of the world’s most recognized art museums. The museum is permanently home to over 300,000 works of art, including such pieces as American Gothic by Grant Wood, Nighthawks by Edward Hopper, A Sunday on La Grande Jatte by Georges Seurat, The Bedroom, 1889 by Vincent van Gogh and The Old Guitarist by Pablo Picasso.
Now, Illinois residents can see these historic masterpieces and much more completely free three days a week.
Read more about the Art Institute of Chicago free days.
19. Embrace “Christmas Around the World” at the Museum of Science+Industry
The Museum of Science and Industry’s beloved annual celebration features a four-story, floor-to-dome Grand Tree, surrounded by a forest of over 50 trees and displays decorated by volunteers to represent the holiday traditions from cultures around the globe.
It’s the one-of-a-kind experience that brings a whole world of holiday joy under one roof and has now returned for its 81st year!
Read more about “Christmas Around the World” at the Museum of Science+Industry.
20. Indulge in the exorbitance of Chicago’s holiday pop-ups
Each year, various bars and restaurants across Chicago transform their spaces and decorate themselves head to toe in an exorbitant amount of holiday decor.
While the boozy milkshakes and Christmas-themed cocktails can sometimes border on the obscene, if there is one time of the year to indulge yourself, we all know it is Christmas time in Chicago.
One of our top picks from the array of Christmas pop-ups in Chicagoland has to be the immersive Santa Baby Pop-Up that takes over Wrigleyville every year.
Here, you’ll find a selection of decadently garnished drinks, mouth-watering cocktails, and a food menu from ‘Santa’s Snack Shack’ offering more than twenty different Christmas-themed bites.
Read more about the best Chicago holiday pop-ups.
21. Try boozy jelly donuts at Wrigleyville’s Hannukah-themed pop-up
It’s not just Christmas pop-ups you’ll find in Chicago. Back by popular demand, Wrigleyville’s Graystone Tavern has resurrected its “8 Crazy Nights” for a fourth year running.
The bright blue bar has emerged from the swarms of red and green to give Wrigleyville’s festive season a vibrant new identity.
The bar commemorates the Jewish holiday with over 8,000 blue and white lights and Hanukkah ball lanterns hanging from the ceiling along with an abundance of other decor and activities.
The menu includes themed drinks and favorites like Latkes, Matzo Ball Soup, Brisket Platter, and decadent Boozy Jelly Donuts made with housemade vodka-infused jelly.
Read more about 8 Crazy Nights.
22. Cozy up at a winterized Chicago rooftop bar
The wintertime can get the better of you. Stay warm this month at many incredible igloos, ski lodges, fire pits, and various inventive solutions at a cheerful rooftop bar in the city. The rooftop view ensures a memorable night in the Chicago skyline that can still be had even as the cold begins to set in.
We’ve compiled a list of the most unique rooftops around Chicago that are still open through winter! From mouthwatering Mediterranean food in cute greenhouses to whimsical winter wonderlands.
Read our list of the best winter rooftop retreats in Chicago.
23. Rent a rooftop igloo at Godfrey Hotel
Boasting Chicago’s largest indoor-outdoor rooftop with a retractable roof, the Godfrey Hotel in River North puts on a whimsical winter wonderland every winter with signature heated igloos where guests can shelter from the winter elements in style with firepits, fire dancing, live DJs, s’mores, and, of course, themed cocktails.
Read more about Godfrey Hotel’s winter wonderland.
24. Head up to London House Chicago’s famed 22nd-level terrace
London House Chicago’s elegant tri-level rooftop bar is another incredible rooftop retreat and has now once again decked out with excessive holiday décor for its over-the-top Rudolph’s Rooftop.
In addition to some of the most unique sweeping panoramic views of Chicago, guests will find rentable outdoor igloos and an ice bar selling holiday-themed cocktails awaiting them on the famed 22nd-level terrace.
Extra-special photo ops in front of the stunning vistas of the Chicago River and Michigan Avenue offer the chance to snap some unforgettable holiday season memories while reveling in the iconic winter wonderland.
Read more about London House Chicago’s Rudolph’s Rooftop.
25. Host your own winter games at the Gwen Hotel luxury rooftop
Another unique winter experience can be had on The Gwen Hotel’s luxury rooftop. While you won’t find lavish igloos here, you’ll instead be able to enjoy the hotel’s annual Curling and cocktails experiences. The hotel kits out its rooftop with not igloos, no ice skating, but an outdoor curling rink high in the sky.
Curling sessions come with a complimentary round of cocktails, meaning you can sip away on your favorite tipple while going toe to toe with your friends on the state-of-the-art curling rink.
Read more about the Gwen Hotel’s curling and cocktails experience.
26. Skate among skyscrapers at the rooftop SkyRink
Rivalling Gwen Hotel for the coolest active rooftop experience is Peninsula Hotel’s SkyRink.
Located on the 4th floor of the award-winning hotel, guests can this winter once again enjoy a one-of-a-kind hybrid rink perched high above Magnificent Mile.
Returning for its 11th season, the Peninsula Sky Rink provides an elevated winter wonderland for 20+ select days through to the end of the year. In addition to a rooftop bedecked in pine trees and Christmas lights, a chalet provides hot beverages and seasonal snacks to ensure skaters are kept well-fueled and well-fed while enjoying the iconic rink.
Read more about Chicago’s SkyRink.
27. Check out the inaugural Wonder City
Peninsula Hotel is, in fact, not the only rooftop skating experience this season. For those who may be unaware, an exciting new soccer experience opened in Lincoln Park last year, taking the city’s sports scene to new heights by providing Chicago with its first rooftop soccer venue.
The 25,000-square-foot rooftop facility has since been offering guests of all ages the chance to train, play, and celebrate the game of futsal and soccer against the stunning backdrop of the Chicago skyline.
Operating for spring, summer, and fall seasons from April to October, the venue has spent November transforming its premises and will next week open as a brand-new whimsical winter skyline escape.
Named Wonder City, the rooftop’s inaugural experience will open on the first day of December, boasting a rooftop ice skate rink, curling lanes, hockey slapshot stations, holiday decorations, and breathtaking photo opportunities in front of panoramic views of the Chicago skyline.
28. Embrace the holiday magic at Gallagher Way’s Winterland experience
Running from Tuesday, November 21, 2023, through Sunday, January 7, 2024, Winterland’s beloved rides and attractions have returned to Gallagher Way including Tilt-A-Whirl, Carousel, Infield Express train, the Umbrella Ride, Flying Dragons, Teacups, and The Edge.
Outside at Christkindlmarket, guests can ride the new 40-foot Ferris wheel and see the dazzling tree that will be lit tomorrow to mark the start of this season’s Winterland.
Read more about Gallagher Way’s Winterland.
29. Get the scoop on the sweetest holiday tradition at The Museum of Ice Cream’s incredible ‘Pinkmas’
Described on the Museum of Ice Cream website as “a Willy Wonka factory come to life that you won’t want to leave,” the Michigan Avenue location opened in 2022 with an array of magical and interactive installations across over 13,500 square feet.
Adding to the experience for the holiday season, the museum has been decked out in pink decor, including an enormous snow globe and various areas for festive crafts.
Guests can expect “a pink wonderland of interactive, limited-time activations like a Pinkmas tree forest, life-sized snow globe and a take-home gingerbread craft activity as well as guest favorites like the iconic sprinkle pool,” according to the release.
Meanwhile, guests can stay warm with seasonal sips and treats from the cafe, including over-the-top ice cream sundaes or holiday cocktails for those 21+.
Read more about Pinkmas at the Museum of Ice Cream.
30. Watch the Art on the MART winter projections
The “largest permanent digital art projection in the world” has begun showing some sensational new shows for its winter program titled ‘Season of Light‘.
Now running through Saturday, December 30, the new winter program celebrates “the emerging and established talent coming from the School of the Art Institute of Chicago (SAIC), a beloved Chicago institution that is internationally regarded as one of the top art and design schools in the world.”
The 30-minute shows will run nightly starting at 7:30 pm and 8 pm through Saturday, December 30th. The best places to view the projections are from the jetty section of the Chicago Riverwalk between Wells and Franklin Streets.
Read more about Art on the MART winter schedule.
31. Send your senses soaring with a Dining in the Dark sushi experience
Take your date night to the next level or embark on a surreal adventure with friends by sitting down for a meal blindfolded to focus on more important things like the exquisite tasting experience.
Dining in the Dark invites guests to engage their taste buds to their maximum in circumstances you’ve like never done before and now for the first time they’ve released a new sushi version of the iconic experience.
Omakase, as defined by Michelin Guide, is a form of Japanese dining in which guests leave themselves in the hands of a chef and receive a meal that is seasonal, elegant, artistic, and uses the finest ingredients available.
This special 12-course menu will surprise you with its burst of flavors encompassing the highest standard of Japanese cuisine all the while focusing on taste and smell alone.
Grab tickets to Dining in the Dark: Sushi “Omakase” Edition.
32. Sip a Guinness at the new Guinness Taproom
In other news, for anybody who loves Chicago beer and has a thirst for that smooth, creamy, world-famous Irish dry stout, you’re in luck! Chicago’s long-awaited Guinness Taproom opened this fall offering the perfect place to grab a drink this December.
The Ireland-based brewer finally opened the 15,000-square-foot Guinness Open Gate Brewery Chicago in West Loop offering a unique new experience in one of Chicago’s most exciting neighborhoods.
Read more about the Guinness Open Gate Brewery Chicago.
33-36. Kick back at a revered brewery
Talking of which, frequently recognized as one of the best beer cities in the country, our seasoned and inventive beer scene has produced so many fantastic breweries and taprooms in Chicago that we’re spoilt for choice.
There are now over 200 breweries, big and small, across Chicagoland, meaning there are plenty of opportunities to enjoy a finely crafted beer in a range of different environments, whatever the weather.
To make sure you’re checking out the best of the best, we’ve here rounded up the 10 best breweries, brewpubs, and taprooms in Chicago. Cheers!
37. Sample the best cocktails in Chicago
If a fruity cocktail is more up your street than craft beer, worry not, for Chicago has an abundance of acclaimed watering holes making sensational cocktails.
Whether you’re treating yourself to brunch in Chicago, kicking back on a Chicago patio, or enjoying drinks out at one of Chicago’s many bars and restaurants, you can be sure a finely-crafted cocktail is only seconds away.
From top-notch margaritas to more innovative cocktail concoctions and everything in between, the Windy City and its abundance of revered mixologists have the answers to whatever it is you’re after.
We’ve recently filtered through the noise to round up the best cocktail bars in Chicago based on our experiences at Secret Chicago, our reader’s most popular choices, and a scrupulous assessment of settings and drink quality.
Read our full list of the best places to buy cocktails in Chicago.
38. Brunch to your heart’s content
If you’re in need of an instant mood boost, searching for a group Sunday Funday activity, or looking to cure a hangover from the night before, brunch is the solution to all problems.
Luckily Chicago has an abundance of seriously good morning eats, and here we’ve compiled the best of the bunch!
Read our full list of the best brunch spots in Chicago.
39. Buckel up for a Drunk Shakespeare show
On the topic of booze, another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show.
On a stage in a hidden speakeasy behind the Chicago Theater, guests will find a glam cocktail bar and library with over 10,000 books. Five classically-trained actors meet as members of “The Drunk Shakespeare Society.” One of them has had at least five shots of whiskey, and then they (quite over-confidently) attempt to perform a major role in a Shakespearean play!
Hilarity and mayhem ensue while the four sober actors try and keep the script on track. Every show is different depending on who is drinking… and what they’re drinking!
Grab tickets to a Drunk Shakespeare show.
40. Chuckle away at Chicago comedy show
If you’re looking for a chuckle, there’s no place better for that than at a Chicago comedy show. Famous for its production of funny guys and girls. Chicago has some of the best places to see a comedy show in the country.
At Laugh Factory Chicago, some of today’s biggest names and local comedians are delivering something for every taste and style throughout the year.
Grab tickets to a show at Laugh Factory Chicago.
41. Hop in a hot tub boat
This season a new unforgettable winter activity has been added to the mix courtesy of The Chicago Electric Boat Company.
Since opening in early 2012, the company has expanded and improved the variety of boats it offers now ranging from 22ft long luxury Duffy boats for 12 passengers to unique donut boats with circular seating designs and round tables that were introduced in 2020.
For over a decade, The Chicago Electric Boat Company has offered a unique, environmentally friendly way to see the city of Chicago thanks to their fleet of rentable 100% electric boats but now a winter addition will join the the Chicago Electric Boat Company fleet, this time in the form of Hot Tub Boat Cruises.
Yes, you read that correctly. Launching out of the docks at Marina City, the new zero-emissions vessels will take up to six people at a time floating along the main branch of the Chicago River in a boat equipped with a fully functioning hot tub.
Read more about the new hot tub boats.
42. Warm-up and revitalize at Chicago’s most unique spas
December is full of magic, but it can also be stressful. Add to that Chicago’s unforgiving frostiness, and you’ve got to consider your well-being during these hostile months. Especially if you’re spending time outdoors exploring nature. Luckily, Chicago is full of answers to combat the Christmas chaos and the numbing chill that settles into your bones.
There is simply no better place in Chicago for some rest and relaxation than AIRE’s Ancient Baths located inside a restored historic River West factory. Inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing, this preserved structure has been restored to its original splendor, and you can now find optimum relaxation within the exposed brick, wooden beams, and industrial columns of the building. A spa day is always the cure for things to do in Chicago in December.
Check out our full list of the best Chicago spas.
43. Tailgate at a Free Fan Fest before the NHL Winter Classic
