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40 Magical Things To Do In Chicago This December

Elliot McGowan Elliot McGowan

40 Magical Things To Do In Chicago This December

There’s snow place like Chicagoland.

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 turbulent year is finally coming to an end. Make no mistake, winters can be as beautiful as they are brutal and despite the chilly weather, Chicago is heading back to normalcy and 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. Pick out a tree at Jacks’ Christmas Tree Farm

Christmas is December’s headline act and without all the lights, decorations, and Christmas trees it wouldn’t be the magical month it is. One of the first things many of us look to do is pick out a Christmas tree and there’s no place better than the Jack Frost Winter Walk and Christmas Tree Farm. As well as a wide selection of fresh Canadian Balsam Firs the interactive pop-up experience offers a larger than life, outdoor, multi-sensory adventure in the heart of Chicago.

Located on over 2 acres in Goose Island, you’ll also find a striking nighttime lights display, an outdoor Christmas-themed party with dozens of Holiday-themed Instagramable memories, and a full-sized Ice Rink.

Grab tickets to the Jack Frost Winter Walk and Christmas Tree Farm here.

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2. Check out Frosty’s Christmas Bar

While the Jack Frost Winter Walk and Christmas Tree Farm offers a 100% outdoor adventure perfect for a magical daytime experience, Frosty’s Christmas Bar is the place to be for late-night fun.

Back for the 2021 holiday season for the fourth year, the over-the-top Christmas pop-up has decked out four bars across 3 levels for the ultimate Christmas extravaganza. With sensational seasonal cocktails, dancing elves, singing Santa, live nutcrackers, wonderfully interactive holiday photo experiences, AND a 4 am closing time, you know you’re in for an eventful evening at Frosty’s Christmas Bar.

Grab tickets to Frosty’s Christmas Bar here.

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3. Go Christmas shopping in Rosemont

Despite the jubilance of the holiday season, it can also be stressful if you’re guilty of leaving your Christmas shopping to the last minute. It’s best to get it done early so that the stress doesn’t build as the month goes on. Luckily, Rosemont has the answer in the form of the award-winning Fashion Outlets of Chicago.

The 530,000 square-foot shopping center is home to over 130 designer outlets and a kids wing that makes it as efficient as it is plentiful. Cutting-edge amenities, concierge services, and unbeatable savings make for a shopping trip that checks all the boxes.

The best part, however, is that a stone’s throw from the Fashion Outlets of Chicago, you’ll find Rosemont’s entertainment district Parkway Bank Park. With over 40 amazing restaurants, 17 luxury hotels, and a jam-packed event calendar you can make it more than just a shopping trip this Christmas.

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4. Skate around an NHL-sized ice rink

Luckily for Chicagoans, Rosemont’s exquisite Chicago Wolves Ice Rink has also now opened for the winter season! An array of twinkling lights illuminate the sublime open-air rink in the middle of Parkway Bank Park’s entertainment district. From now through February 27th festive tunes will echo through the air as people of all ages lace up, take to the ice, and swirl and soar through the winter mist.

The climate-controlled NHL-sized rink is absolutely free if you have your own skates and just $8 to rent a pair onsite!

More information can be found here.

5. 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.

6. Enjoy curling and cocktails at Gwen Hotel

Another unique December experience can be had up on The Gwen Hotel’s luxury rooftop. Every winter the hotel kits out its rooftop out 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.

7. 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.

8. Board the CTA Holiday Train

Santa’s holiday train trip around Chicago is always one of the most eagerly anticipated Christmas events 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. The mere sight of the CTA Holiday Train or Holiday Bus is enough to brighten anyone’s day but jumping on board to be serenaded by jolly elves is the real experience.

This year guests will once again be able to jump on board after inevitable changes last year though face masks will be required this year no matter age or vaccination status. The CTA Holiday Train will travel all 8 lines from Friday, November 26 through Wednesday, December 22nd while the CTA Holiday Bus will travel 14 different routes serving all areas of the city from Tuesday, November 30th through Thursday, December 23rd.

You can find the full schedule here.

9. Sip Glühwein at Christkindlmarket

Chicago’s German-inspired annual Christmas market is another extremely popular Christmas event. After taking to the internet last year, the 25th edition of the beloved Christmas market has now returned and will run through to Christmas.

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.

10. Check out Blitzen’s holiday pop-up and winter market

On Dasher, on Dancer, on Prancer, on Vixen, on Comet, on Cupid, on Donner, on Rudolph and on…Blitzen! The most wonderful time of year is near and Blitzen’s holiday pop-up, a holiday market experience, has some jolly good times in store for you: Christmas lights and joyful bites, candy cane swings and festive things, kisses under an enormous mistletoe, and maybe even a bit of snow… In an illuminated multi-level venue decked floor to ceiling in holiday decor, you’ll get to immerse yourself in the magic of this Christmas season.

Get your tickets for this merry pop-up coming to Chicago on December 16!

11. Embrace Christmas in all its colors at Sleigh Bells

The holidays turn multicolor this December with “Sleigh Bells: A Kaleidoscopic Christmas” coming to Chicago’s historic Medinah Temple this December. The prismatic experience puts a trippy twist to the traditional Christmas pop-up. Sparkle along to twinkling LED tunnels—each as inspired from noel as the next. From large infinity mirror ice caves to immersive projection mapping, the fleeting store’s seasonal-themed art installations will make the yuletide gay.

You can grab tickets to Sleigh Bells: A Kaleidoscopic Christmas here.

12. Hit up the Hubbard Inn Holiday Pop Up

Tis the season and Hubbard Inn has fully transformed to The Christmas Inn to make your holidays on Hubbard Street merry and bright! Experience 3 levels of holiday bliss with festive cocktails, Instagrammable moments and live entertainment at this limited-time holiday pop-up! Each floor has its own Christmas theme, with the classic magical Christmas on the first floor, 60’s ‘Kitchmas’ vibes on the second floor, and the third floor Christmas apocalypse.

From brunches and mixology classes to holiday trivia nights and paint and sip classes, there is entertainment scheduled throughout each week at Hubbard Inn this holiday season!

You can grab tickets to Holidays on Hubbard Pop Up here.

13. 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 2021. 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.

14-17. Enjoy a light show or three

Photography by Alex Hewitt

Chicago’s many light shows are some of our most treasured winter traditions and they’re coming back thick and fast to the Windy City this year! In 2020 all light show experiences turned to drive-thru events or were heavily adapted hindering the real light show experience. This year they’ve returned to their true formats and in some cases expanded and evolved.

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.

Head to our list of 10 magical must-see light shows in and around Chicago for more.

18-22. Be captivated by a Christmas Candlelight Concert

Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but this Christmas there are some extra special holiday-themed concerts taking place. Flickering candles and melodic sounds combine phenomenally creating magnetic atmospheres and some of Chicago’s most unique venues. Wrap yourself in seasonal nostalgia with awe-inspiring renditions of classics across genres. Here are some of our favorite festive concerts taking place this month:

See the full list of candlelight concerts taking place in Chicago here.

23. 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 dining, drinking, and the magic of jazz in a truly vivacious venue.

Grab tickets for Immersive Live Jazz & Dinner for Two here and Immersive Live Jazz & Cocktails here.

24. Marvel at musical masterpieces in a repurposed landmark church

West Loop’s Epiphany Center for the Arts has announced a new Acoustic Music Series that will take place within the recently restored landmark venue and it looks like a match made in heaven.

Stepping inside the illustrious 19th-century national landmark is already an experience in itself. The fortress-like former church and its iconic bell tower have long towered above the West Loop skyline since it was first assembled back in 1885. What lies inside is a glorious architectural achievement with exposed beams and sweeping arched trusses.

Now, despite being decommissioned and listed as permanently closed a decade ago, the venue’s heart beats louder than ever before with an ongoing lineup of live performances that showcase the extraordinary acoustics found within.

More information and tickets can be found here.

25. Unleash your inner artist at Epiphany Center for the Arts

Acoustic music series isn’t the only form of art taking place at Epiphany Center for the Arts this month. Thanks to a collaboration between Epiphany Center of the Arts, Studio W.I.P. and local Chicago artists, a new series of interactive street art workshops invites you to exercise your inner creativity and learn the ins and outs of urban art in Chicago.

Taking place most Fridays through winter at the iconic Epiphany Center of the Arts, anybody and everybody can be enlightened and educated by some of Chicago’s tried and tested street artists. These interactice street art workshops provide the perfect setting in which to nurture an interest in street art while simultaneously offering a fun and laid-back experience. With your own canvas, a selection of professional-grade spray paints, a library of stencils, and Epiphany Golden Hour food and drink specials, guests can learn the tricks of the trade with a spray can in one hand and a drink in the other!

26. Peruse the magnificent street art murals of Chicago

If you’re needing some artistic inspiration you need not look far in the Windy City. The consequence of a thriving artistic community is not just a plethora of museums and stunning art installations. 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.

The many masterpieces in our great city can be even more spectacular in the winter snow and an adventure hunting down the very best creations will always be always time well spent.

27. Discover West Town street art with a local

One of the best places to see Chicago’s street art is known as the B_Line. The mile-long street art corridor under a historic train line in Chicago’s Fulton Market meatpacking district is an accessible immersive art experience. The B_Line began as a quest to resurrect one of Chicago’s most rare displays of public art. Now, the B_Line has evolved into an idyllic place for unique individuals to congregate just off the beaten path, in the backyard of the Fulton Market District.

This immersive street art tour is operated by a local guide with a passion for street art and an in-depth knowledge of the most remarkable murals and their history.

28. Take a trip through time with a Gangsters And Ghosts Tour

A walking tour might just have you wanting to really immerse yourself in the history of this great American city, right from the locations that started it all. Chicago’s Gangsters And Ghosts Tour is another brilliant walking tour that visits the locations frequented by some of Chicago’s most notorious gangsters along with many of the most haunted locations in Chicago!

You can get the best of both worlds with this 2 in 1, history-based guided walking tour of Chicago’s gangsters and ghost stories, right from the famous Chicago Loop Vice District!

29. Let Blue Man Group blow your mind

While this month will be filled with Christmas events of all kinds, the awe-inspiring Blue Man Group shows are truly in a category of their own. The global entertainment phenomenon has returned to the Briar Street Theatre in Chicago and presents an unmissable opportunity to see the renowned act at work. Known for its award-winning theatrical productions, iconic characters, and creative ingenuity, Blue Man Group performances promise a witty, roller-coaster-paced multisensory spectacle.

Fit for all demographics, be it couples, family, friends, and groups of any shape or form, these visually stunning performances guarantee you’ll be leaving with a grin from ear to ear and a spring in your step.

Grab tickets to these electric performances here.

30. See the largest official interactive ‘The Office’ experience in Chicago

The largest official interactive The Office experience has now opened in Chicago. Through January 17th, fans of the long-running hit series will be able to immerse themselves in the world of Dunder Mifflin Paper Company and celebrate their favorite characters and iconic moments from the hit show.

The interactive two-story experience will feature 17 rooms filled with original props, costumes, set re-creations, and more. Celebrating the series’ major characters and timeless charm there will be photo ops at places like Pam’s desk, Michael’s office, Ryan’s closet, Schrute Farms, and others as well as a themed retail store replicating the Warehouse

More information can be found here.

31. Have a good chuckle at a Drunk Shakespeare show

Another brilliant experience taking place this December 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.

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32. Enjoy an evening with Teatro ZinZanni

Of course, there are plenty of theatrical events taking place this month and you’ll find few that live as long in your memory as an experience with Teatro ZinZanni at the opulent Spiegeltent ZaZou.

Located on an entire floor of the Cambria Hotel in the heart of Chicago’s Downtown Theater District, a giant unique jewel box mirror tent now offers an eccentric escape from the day to day. The Spiegeltent ZaZou is an unabashedly extraordinary domain glimmering with mirrors, chandeliers, and grandiose glamour but it’s the kaleidoscopic contents of an evening with TeatroZinzanni that will have you forgetting all about the world outside.

Described as “dynamic, hilarious and delicious”, Teatro ZinZanni is a whirlwind of international cirque, comedy and cabaret served with a multi-course feast. As the fast-paced action unfolds around, above and alongside guests, they are invited to dine, drink and delight in the evening’s events.

Grab tickets to a night with Teatro ZinZanni here.

33. Be beguiled by a burlesque show

A number of fantastic burlesque shows offer an exhilarating night out in Chicago this December. Featuring world-class acrobats and unbelievable stunts the AirOtic Soireé Cabaret Dinner Show at Joy District provides another unforgettable night.

Prepare for a night of immersive entertainment, sharing a story of love, passion, sexuality and eroticism! Extravagant costumes, seductive choreography, Adonis physiques, unbelievable stunts and circus artistry are sure to leave you on the edge of your seat begging for more! But wait there is more…after the performance enjoy decadent cocktails and meet the performers from the show!

Grab tickets to here.

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34. Feast on a bottomless brunch at The Grand Cabaret

If Jazz and Cabaret are your thing but so too are bottomless brunches, Porkchop and the Grand Cabaret speakeasy have the ideal Saturday with their Boozy Jazz Brunch! Make every Saturday a brunch Saturday and start your weekend off with a bang! Choose a delicious brunch from the menu and tuck into some delicious cocktails. Songs, dance and so much more await—it’s the most fun you can have on a Saturday morning!

Grab tickets to a Boozy Bottomless Mimosa Brunch and Live Jazz here.

35. Head out of the city and see Illinois’ natural spectacles

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Ok, this last one isn’t strictly in Chicago we know. But with so much going on in the city it can be nice to escape to the quiet of Illinois’ natural beauty. Though our state may not boast wonders with the universal magnitude of the Grand Canyon nor the grandiose reputation of Niagra Falls, Illinois is teeming with diverse ecological landscapes that transform into incredible winter wonderlands this time of the year. From monolithic marvels covered in snow to cascading waterfalls frozen in time, here are 7 natural wonders of Illinois that you can visit while they’re a different beast in winter:

  • Garden Of The Gods: Saline County
  • Wildcat Canyon In Starved Rock State Park: La Salle County
  • Cache River State Natural Area: Johnson County
  • Cave-In-Rock: Hardin County
  • The Pomona Natural Bridge: Jackson County
  • Cascade Falls In Matthiessen State Park: La Salle County
  • Bork Falls In Ferne Clyffe State Park: Johnson County

More information can be found here.

36. Warm-up and revitalize at Chicago’s most unique spa

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 wellbeing into consideration during these hostile months. Especially if you’re spent 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.

37. Treat yourself to a beer bath

Another spa option comes in the form of PIVA Beer Spa where guests can sink back into a huge larch wooden tub filled with near 100-degree beer, herbs, and hops. Whilst swearing that soaking in beer can have numerous benefits, PIVA Beer Spa provides a variety of services both beer-related and non-beer related from rejuvenating salt room experiences to luxury massages.

More information can be found here.

38. Try a virtual whiskey tasting experience

Not ready to go out and about just yet? No worries! Why not enjoy a luxurious night-in with Rabbit Hole Distillery instead? This Virtual Tasting Experience is the ultimate at-home indulgence – you’ll get a tasting kit full of award-winning Rabbit Hole Whiskey delivered to your door. And you’ll get to take part in an intimate virtual guided tasting session from the stunning Rabbit Hole Distillery in Louisville!

Whether you’re a whiskey connoisseur or a total novice, you’re guaranteed a good time at this unique tasting experience. You’ll learn more about Rabbit Hole’s small-batch American whiskey as you enjoy a guided tasting of two award-winning expressions with a real Rabbit Hole Distillery Tour Guide. It’s the perfect way to treat a loved one (or yourself!) to a fascinating and delicious night-in.

Get your hands on tickets here.

39. Check out the Princess Diana Exhibit coming to Chicago

For the first time ever, world-famous royal photographers (Anwar Hussein and his two sons Zak and Samir) will be sharing their experiences with the iconic princess and her family throughout December and tickets are selling fast.

Princess Diana, by most accounts, is the most photographed human in history. She grew up in the public eye. One of the people that was there capturing the biggest and most important moments was Royal Photographer Anwar Hussein. Later, his sons Zak and Samir joined the family business.

The exhibition, now in Chicago, is told from their perspective: what they heard, what they saw, what they witnessed first-hand will all be shared. This is not a story you have heard before. Whether you are a hard-core fan or new to her legacy, you will be blown away by the fascinating depth and detail shared by the Hussein family.

Grab tickets to the Princess Diana Exhibit here.

40. Attend the Queen’s Ball

Talking of royalty, your presence is soon requested at the most exclusive ball of the season! Now is your chance to secure your invitation to an immersive experience transporting you straight to the Regency era. Prepare to mingle with other members of the Ton as you sip on cocktails and partake in an evening of music and dance. Rumour has it that Her Majesty Queen Charlotte is looking for the diamond of the season, but will you be the one to win her favor?

Grab tickets to the Queen’s Ball here.

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