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 coming to an end.
Make no mistake, winters can be as beautiful as they are brutal and despite the chilly weather, there is plenty going on.
Here’s a list of the best things to do in Chicago with both activities worthy of stepping outside to brave the Chicago chill and some you can do from the warmth of the indoors.
From light shows to Christmas pop-ups here are our best December-time activities in and around Chicago.
1. 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 rinks 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 and now it’s also free Monday-Thursday if you bring your own skates!
More information can be found here.
2. Sip Glühwein at Christkindlmarket
Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event and the beloved Christmas market is back and this year, it’s been voted the 3rd best holiday market in the world!
This year both The Christkindlmarket Daley Plaza and The Christkindlmarket Wrigleyville are welcoming guests into villages to peruse handmade gifts whilst enjoying German food and beverages beneath the snowflakes and glistening lights.
Enjoy the smell of roasted nuts, fresh pretzels, bratwurst, hot spiced wine, and the magic of festive music all in the coziest of atmospheres!
More information can be found here.
3. Ride the CTA Holiday Train
One of Chicago’s most cherished Christmas events is back for the season. Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated activities providing affordable fun for all Chicago families.
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.
Now in its 31st 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 8 lines through Monday, December 19th.
The CTA Holiday Train and Holiday Bus schedules plus more information can be found here.
4. Check out Chicago’s Harry Potter experience
It’s the most magical time of the year and what pop-up could be more magical than one that allows you to revel in the wizarding world? Witches, wizards (and even muggles!) can finally embark on an incredible journey to Hogwarts™ at the worldwide premiere of Harry Potter™: Magic at Play, exclusively in Chicago.
The massive Harry Potter™: Magic at Play experience has finally arrived in Chicago, taking over three floors at the Water Tower Place on Michigan Avenue, where guests of all ages can interact, explore, play, and climb their way through the most iconic moments at Hogwarts™.
Don’t miss this magical adventure for wizards, witches, and even muggles (gasp!)—Accio tickets!
5-10. Check out a holiday light show or three
Chicago’s many light shows are some of our most treasured winter traditions. In 2020 all light show experiences turned to drive-thru events or were heavily adapted hindering the real light show experience and making us all realize just how much we took them for granted.
Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine providing some of Chicago’s most magical multi-sensory events and we’ve rounded up the best of them all.
- Lightscape at Chicago Botanic Garden
- Illumination: Tree Lights at The Morton Arboretum
- ZooLights at Lincoln Park Zoo
- Holiday Magic at Brookfield Zoo
- AMAZE Light Festival at Odyssey Fun World
- Shine Light Show at Northbrook Court & Schaumburg
11-15. Be captivated by a Christmas Candlelight Concert
Step into Chicago’s most exquisite spaces to experience some of the most treasured holiday classics. From Christmas 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.
Here are some of our favorite festive concerts taking place this month:
- Candlelight: Holiday Special feat. “Silent Night, “Jingle Bells,” and More at Oak Park Arts Center (Now with an extra concert due to demand!)
- Candlelight: Holiday Special featuring “Silent Night, “Jingle Bells,” and More at Stan Mansion
- Candlelight: Latin Christmas featuring Luis Miguel, Celia Cruz, Jose Feliciano at Salvage One
- Candlelight: A Tribute to Queen and More at Oak Park Arts Center
- Candlelight: A Tribute to Queen and More at Theater on the Lake
See the full list of candlelight concerts taking place in Chicago here.
16. Gift a loved one a Candlelight Concert
Struggling to think of a present for somebody? Gift somebody an exclusive concert illuminated with thousands of candles. Choose from concerts featuring jazz, rock, pop, classical music, and even movie soundtracks in spectacular venues around Chicago.
Candlelight gift cards are really easy to use and valid for any Candlelight event making it a unique and exciting gift for friends or family!
Get your Candlelight gift card valid for any Candlelight concert in Chicago or any other city in the U.S. here.17. Enjoy an intimate live jazz show at Le Piano
When it comes to live music, few places offer a better jazz experience than Chicago. There are so many wonderful places to see live jazz in its rawest form here in the Windy City. Alongside esteemed venues like South Loop’s The Jazz Showcase, and Uptown’s Green Mill Cocktail Lounge, Le Piano has emerged as a phenomenal new jazz hideout.
In the middle of Le Piano sits a magnificent grand piano where some of Chicago’s most talented pianists and jazz performers come to play. Here you will find a mind-blowing musical experience merging dinner and intimate performances. Immersive Live Jazz & Dinner for Two and Immersive Live Jazz & Cocktails both ensure memorable nights of fine dining and drinking cocktails in a truly vivacious venue.
Grab tickets for an unforgettable live jazz experience here.
18. Indulge in the exorbitance of Chicago’s Christmas 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 at times 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 Deuce’s Major League Bar in Wrigleyville every year.
Here you’ll find a wide selection of decadently garnished drinks and mouth-watering cocktails as well as a food menu from ‘Santa’s Snack Shack’ providing more than 20 different Christmas-themed bites.
More information can be found here.
19. 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, The Graystone Tavern has resurrected its “8 Crazy Nights” for the third year running. The bright blue bar has emerged from the swarms of red and green with the objective of giving Wrigleyville’s festive season a vibrant new identity.
The bar is commemorating the Jewish holiday in its spacious and enclosed new weatherproof patio with over 8,000 blue and white lights and Hanukkah ball lanterns hanging from the ceiling. The food menu includes favorites like Latkes, Matzo Ball Soup, Brisket Platter, as well as decadent Boozy Jelly Donuts made with housemade vodka-infused jelly.
Make sure to order the 18-foot giant menorah “shotski,” starting at $24, so all your friends can take a shot at once. There will also be a photo booth with Hanukkah Props where you can mark your crazy night out with hilarious snapshots.
You can find more information here.
20. Drink in a personal snow globe
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. The clear-domed igloos cover the rooftop’s portico and offer the perfect place to cozy up with a cocktail, s’mores, and sweeping skyline views.
More information can be found here.
21. Head up to London House Chicago’s famed 22nd-level terrace
The luxury hotel’s elegant tri-level rooftop bar is 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.
More information can be found here.
22. Enjoy curling and cocktails at Gwen Hotel
While many rooftops decorate their spaces with igloos and cozy escapes, The Gwen Hote does things a little differently each year. Every winter the hotel kits out its rooftop with an outdoor curling rink high in the sky for the hotel’s annual Curling & Cocktails experiences.
Curling sessions come with small bites and a complimentary round of cocktails meaning you can sip away on your favorite tipple while battling your buddies on the state-of-the-art curling rink.
More information can be found here.
23. Check out Chicago’s extravagant new mini golf cocktail bar
If those kinds of competitive leisurely activities are up your alley, you might want to check out Chicago’s brand new mini golf concept bar, Puttery, which fuses high-tech gameplay with craft cocktails and curated cuisine!
The exciting new mini-golf and cocktail experience transports guests to wholly unexpected locations while motivating competitive socializing.
According to an official release, the new 23,000-square-foot venue in the heart of Fulton Market District features “uniquely themed putting courses, stunning bars and swanky lounge spaces within a lively atmosphere to provide an unmatched immersive experience.”
24. Immerse yourself in The Art of the Future at Holographic Art Gallery
Another incredible December event taking place this month can be found at Navy Pier. At Verse: The Art of the Future art and technology come together allowing you to step right into the metaverse in a digital art exhibition featuring augmented reality holograms and artwork by top-selling artists from the burgeoning world of NFTs.
With the help of an AR headset, smartphone, or tablet, each guest will experience their own reality in the same activation area (like a silent disco for holograms!). Verse provides an introduction to the people, technology, and stories that are shaping this disruptive evolution of the art world.
Get your tickets for Verse: The Art of the Future in Chicago here!
25. Immerse yourself in the mind of Vincent Van Gogh
Have you ever dreamt of stepping into a painting? Though a little out of the way in Michigan’s Grand Rapids, we can’t help but strongly suggest you take the short drive and do just that.
At Van Gogh: The Immersive Experience guests can take an awe-inspiring journey into the incomparable universe of one of the greatest artistic geniuses of the 19th century. Explore his life, his work, and his secrets as never before through cutting-edge 360-degree digital projections, a one-of-a-kind VR experience, and a uniquely atmospheric light and sound show.
This unique experience brought to you by Exhibition Hub has already thrilled 2 million visitors in the USA, in New York, Atlanta, Washington DC, and Boston, among other cities like London. Become completely immersed in the works of art around you, and feel the shift in reality as you dive deep into the world created by Van Gogh’s brush strokes.
Grab tickets to Van Gogh: The Immersive Experience here.
26. Revel in the raucous The Roar: A Prohibition Era Speakeasy
If Prince has you recalling your bygone days, go back in time even further to Chicago’s Prohibition Era at The Roar on Rush! A lively Speakeasy that lights the way to a hidden 4-room cocktail experience where you will meet vibrant figures from the elaborate web of a Roaring Twenties bootlegging operation. Each room tells a story and is paired with a cocktail tasting from Prohibition times! Afterwards, take a seat in the Speakeasy for more cocktails, food, and live music with special performances. Break out your best flapper dresses and linen jackets, this cocktail party at The Roar is not to be missed!
27-29. Head down to the Grand Cabaret After Dark speakeasy
If you really want a buzz we suggest you head down to Porkchop’s speakeasy “Grand Cabaret After Dark” in West Loop this month for a roster of rip-roaring revelry.
On Fridays’s STRIPPED provides a decadent and debaucherous night of burlesque while on Saturdays the dynamic burlesque performances continue courtesy of BimBamBoom for Peep Show Burlesque.
Both action-packed shows are no-holds-barred adult fun that makes for the weekend night adventure and then Boozy BBQ Drag Brunches on Sundays are there to help you soothe the Sunday scaries.
Check out all the chaos going on at Porkchop’s Grand Cabaret After Dark here!
30. Chuckle away at Chicago comedy show
We could all do with a chuckle after the tumultuous last couple of years and luckily there’s no place better for that than at a Chicago comedy show.
At Laugh Factory Chicago some of today’s biggest names and local comedians are delivering something for every taste and style throughout November.
Grab tickets to a show at Laugh Factory Chicago here.
31. Drink cocktails at the new 360 CHICAGO bar up in the clouds
Talking of cocktails, a new bar has opened 1,000 feet above Chicago up on the 94th floor of the former John Hancock Center. European design meets Chicago’s neighborhoods at 360 CHICAGO’s CloudBar. The 18-seat lounge bar celebrates the 77 boroughs with a locally inspired menu, and illustrations from renowned Chicago street artist— Lauren Asta.
Sip on an Orange Line or opt for the Gold Coast Manhattan and take in the breathtaking views at the $2 million lounge this month.
32. Embrace the holiday magic at Gallagher Way’s activity-filled Winterland experience
This year, Winterland is extending onto the iconic Wrigley Field. Step foot on the infamous greenery for a fantastic winter wonderland experience featuring a series of engaging games, like ice bumper cars, and carnival rides. There’s so much fun to be had at the annual event! Bundle up and embrace adventure with a trip down the ice slide, or cozy up and enjoy a perfect treat with a make-your-own s’mores kit!
Winterland is filled with on-field games, and new rides like the Winter Tube, the Infield Express, and the Winter Whirl. Don’t miss out on a scenic view of the field with a nostalgic train ride on the brand-new holiday train. Embrace heights with a trip around the nostalgic carousel, then lace up a pair of skates and hit the ice for a whirl around the iconic rink!
33. Get your shopping done at a one-of-a-kind holiday market
It’s only officially the holiday season when the beloved Merchandise Mart is back in town! Here in Chicago until the 4th, the inventive market features endless unique handmade offerings in one place. The annual holiday market has become a staple with over 21 years of events! Filled with over 500 individual artists, makers, and designers selling everything from ceramics to home goods to to photography, ensuring you’ll find something for everyone on your list.
34. Catch an Art on the MART winter projection
We’ve been treated to many months of stunning art spectacles on the facade of the Merchandise Mart since they returned earlier in 2022 for a climate change-themed spring program in collaboration with Shedd Aquarium.
Now the “largest permanent digital art projection in the world” has begun showing some sensational new shows for its winter program. “Chicago Design Through the Decades” by Daria Tsoupikova, Sharon Oiga, and Guy Villa Jr and The Nutcracker by Joffrey Ballet of Chicago will light up the 2.5-acre river façade at 7:30 & 8 pm nightly, changing from the 8.30 and 9 pm summer and fall showing times.
More information can be found here.
35. Peruse the magnificent street art murals of Chicago
The consequence of a thriving artistic community in Chicago does not stop at its many museums and visual creations like Art on the MART. Today the street art and graffiti scene in Chicago is alive and kicking more than ever before with new pieces popping up all over the city every week. Some of these are so esteemed that they’ve embedded themselves in the very fabric of Chicago and are now part and parcel of the Windy City’s identity.
With more formality and respect from the local community street art has thrived in Chicago over the last decade and with the events of the last two years many, many, astounding new murals have gone up of late. Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for racial equality, celebrate different heritages, and honor the essential workers of our societies during turbulent times.
Hunting down the many masterpieces in our great city is a rewarding experience any time of the year. Many of these wonderful murals reside in West Town in the mile-long street art corridor in Chicago’s Fulton Market meatpacking district known as the B_Line. With the West Town Street Art Walking Tour run by Tours By Native you can enjoy an immersive tour that will engage the senses like never before!
Grab tickets to the West Town Street Art Walking Tour here.
36. Savor sensational food samples on a food tour
For foodies who prefer to sample tasty delicacies over perusing extraordinary street art, there is a range of fantastic food tours for all manner of foodies.
Taste all of Chicago’s classic eats on a four-hour guided bicycle tour courtesy of America’s longest-running city bicycle tour company with Bikes, Bites, and Brews: Chicago’s Signature Dishes Bike Tour. The journey is 14 miles in total (traversed at a nice leisurely pace) and includes a slice of deep-dish pizza, a gourmet brownie, a Chicago-style hot dog, and a few samples of Chicago’s legendary craft beer!
Despite having a kaleidoscopic food scene offering all manner of savory and sweet treats, nothing in Chicago has truly celebrated donuts in all their glory, until now. The Underground Donut Tour is Chicago’s first-ever donut tour and was born to give those who truly enjoy donuts the perfect excuse to sample the Windy City’s very best. Tours include such favorites as Do-Rite Donuts, Firecakes, Stans, and Doughnut Vault as well as some lesser-known spots.
Grab tickets to the Bikes, Bites, and Brews tour here or a donut tour here.
37. Revel in the pandemonium of a Drunk Shakespeare show
Another brilliant Chicago experience comes in the form of a live Drunk Shakespeare show. Taking place on a stage in a hidden speakeasy located 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 5 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 here.
38. Enjoy an incredible holiday aerial performance
Everything turns to jolly cheer this time of the season including Broadway in Chicago. Performing a routine of spectacular numbers from December 6th through December 11th, Magical Cirque Christmas is a holiday show with stunning aerial feats and the classic tunes of beloved holiday music that will be sure to startle and surprise.
Grab tickets to a Magical Cirque Christmas show here.
39. See a live rendition of ‘Herschel and the Hanukkah Goblins’ this season
As soon as Magical Cirque Christmas comes to a close Herschel and the Hanukkah Goblins begins.
From December 11 through the 31, head to the Strawdog Theater for a rip-roaring family-friendly performance. The show is based on a popular book by Eric Kimmel and tells the story of a traveling troupe of actors, who bring the Hannukkah magic to life in a riveting, unmissable show.
Adapted for the stage by Mike Dailey with music and lyrics by Jacob Combs, this exciting live performance is as riveting as it is memorable.
More information can be found here.
40. Sing your heart out at the Millennium Park Holiday Sing-Along
If all the talk of live performances has you feeling theatrical you can celebrate the joy of the holidays with a 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 ongoing until December 16th.
More information can be found here.
41. Embrace “Christmas Around the World” at the Museum of Science+Industry
Delight in the spectacle of light at this year’s Christmas around the world, an annual tradition featuring over 50 trees to highlight a variety of countries and cultures. Now in its 80th year, this annual tradition offers museum-goers a cool bit of insight into customs celebrated by people around the world.
Decorated by volunteers, the stunning exhibits showcase global traditions, including the main centerpiece: a towering four-story Grand Tree!
Tickets are included with general museum admission.
42. Get the scoop on the sweetest holiday tradition at The Museum of Ice Cream’s incredible ‘Pinkmas’
Another museum you’ll want to check out is this season is one dedicated to all things ice cream. Add an extra sprinkle of joy to your holidays at the Museum of Ice Cream’s annual Pinkmas celebration– open now for all to enjoy!
Explore over 13,000 square feet of engaging interactive exhibits like a themed enchanting tree forest and a towering snow globe. There’s plenty to do outside of the exhibits themselves, like festive arts and crafts where you can a make-your-own gingerbread house.
Don’t miss out on the giant red and pink sprinkle pool, either. It’s the perfect place to wash your holiday stress away with a dip in the sugar-coated extravaganza.
43. Enjoy the legacy of a music icon at Prince: The Immersive Experience
The Purple One’s fans can rejoice and party like it’s 1999 because this jaw-dropping Prince experience has been extended, but not for long. You’ll be able to step into Prince’s universe in Chicago until the end of December.
Journey through 10 multidimensional spaces of musical genius in downtown Chicago before the experience leaves for good. If you have a Prince fan on your list, this journey through his universe won’t disappoint. Plus, a gift shop on the ground floor is filled with exclusive merch.
Lose yourself in Prince’s enigmatic universe and get your tickets now!
44. Create a cozy winter hideout at these magical Chicago rooftop bars
The wintertime can really get the better of you. Stay warm this month at any number of incredible igloos, ski lodges, fire pits, and various inventive solutions at a cheerful rooftop bar in the city. The rooftop view ensures it’s a memorable night up among the Chicago skyline that can still be had in the months to come.
We’ve put together a list of the most unique rooftops around Chicago that are still open through winter! From mouthwatering Mediterranean food in cute greenhouses to curling competitions with complimentary cocktails. Check out these awesome Chicago rooftop spots.
45. Gaze at the stars at the Adler Planetarium for free on a Wednesday
If looking up at the skies has you in awe of what’s out there there’s no place better to feed your curiosity than at Chicago’s Adler Planetarium. The planetarium recently reopened after a two-year hiatus and now boasts a brand new telescope in the Doane Observatory which holds the title of the largest public telescope in the Midwest.
As well as a new observation park, guests will notice the planetarium’s shiny new dome roof which has been restored with brand-new copper tiles giving the 80-year-old dome an iconic new glow. The best news, however, is that Illinois residents can enter for free every Wednesday evening from 4-10 pm provided they bring proof of residency.
More information and tickets can be found at adlerplanetarium.org.
46. Head out of the city and see Illinois’ natural spectacles
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47. Stay in a Starved Rock Getaway cabin
One magical natural escape, Starved Rock State Park, has just opened a selection of minimalistic cabins with floor-to-ceiling windows allowing guests to wake up fully immersed in the wilderness.
Located in lush landscapes and with minimalistic yet comfortable designs, they offer the perfect escape for those wanting to disconnect from busy city lives with restorative stays in the middle of nature.
Undoubtedly one of our state’s most impressive natural spectacles, Starved Rock offers over 13 miles of hiking trails, numerous cascading waterfalls, and 18 different canyons.
More information can be found here.
48. Try an indoor skydiving experience
If you’re the outdoorsy type who likes a thrill you might be the type who would be interested in testing your skydiving skills in one of Chicago’s state-of-the-art indoor skydiving centers. With an iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, there are two conveniently located cutting-edge centers to choose from.
Kids and adults can both experience the same sensation you’d get 12,000 feet up in the sky and if you feel you have what it takes, you can test your vertigo above Chicago’s iconic skyline at Skydive Chicago, one of the world’s largest skydiving resorts.
Grab tickets to an indoor skydiving experience here.
49. Warm-up and revitalize at Chicago’s most unique spas
Christmas is full of magic but it can also be stressful. Add to that Chicago’s unforgiving frostiness and you’ve got to take your well-being into consideration during these hostile months. Especially if you’re spending time outdoors exploring nature. Luckily Chicago is full of answers to combat both 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.
50. Give the best gift experiences this holiday season
There’s so much to experience this holiday season, from a themed party bus to endless light shows, and other exciting holiday traditions. As the season is bustling with activity, and you can’t think of a physical gift this year, why not gift them an unforgettable experience?
You can find the full list here.
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