40 Amazing Activities For An Unforgettable January In Chicago

Elliot McGowan Elliot McGowan

40 Amazing Activities For An Unforgettable January In Chicago

It’s time to finally say goodbye to 2021, and welcome in 2022.

January is here marking the end of another of the most turbulent years in our recent history. We start off a year anew with renewed hope, vaccines are in circulation, Chicago is alive and kicking and we’ve taken another step towards normalcy.

The Midwest’s icy winter has now begun settling in after the latest first measurable snowfall since records began finally arrived, and we’ve got a whole list of exciting things to do in the Windy City.

From escape rooms to rooftop soirées here’s a list of awesome activities for an unforgettable January in Chicago whether you’re a long-time local or an enthusiastic tourist.

1. Experience “alpine in the city” at Maggie Daley Park

Photo from Instagram / @borntoseephoto

There’s no better way to glide into 2021 than with some winter skating. 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 in January if you bring your own skates!

10-15. Be captivated by a Candlelight Concert

Chicago’s sublime Candlelight Concert series offers breathtaking spectacles throughout the year but this January there are some extra special concerts taking place including tributes to Amy Winehouse, Taylor Swift, ABBA and Stevie Wonder.

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.

16. 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.

17. 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.

18. 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!

19. 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.

20. Discover Chicago’s urban graffiti and murals with a local

If you’re not too familiar with Chicago’s art scene, worry not. There are many who pride themselves on their knowledge and love to rhapsodize about the wonderful murals of Chicago and if you’d rather seek out the best murals in Chicago with the help of a local the Offbeat Street Art Tour of Chicago is for you. No other tour takes guests out into the streets to showcase and highlight the vibrant street art scene which many people overlook on a daily basis. Join this experience that is truly unique to Chicago for a one-of-a-kind experience!

Tickets and more information can be found here.

21. Take a trip through time with a Gangsters & 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!

22. Savor a Secret Food Tour in the Loop

Photo: @musthavegonetojared

Only Chicago’s gastronomy scene is as revered as Chicago’s art scene and on a tour of the Loop, you’ll find some of the very best. If you prefer to hear from those in-the-know rather than navigate the streets yourself, this is for you. On this 3-hour tour of Chicago’s food scene, you’ll see what sets this friendly mid-western metropolis apart. A local guide will share with you some hidden gems of the ‘Chicago Loop’ and reveal some great stories about the city. Taste where the world-famous dipped Italian beef sandwich was invented, try some of the best deep dish Chicago pizza, and really appreciate how important the immigrants that built this town are to the food scene.

Tickets and more information can be found here.

23. Go on a self guided foodie adventure

Discover Chicago’s food scene under the magical cloak of winter. An all-inclusive organized tour will send you searching the hidden corners of Chicago for clues and riddles. These will help you find your way around the region collecting a delicious selection of gourmet food and drinks from small local businesses. There will be pre-paid picnic items to collect along the way with vegetarian, vegan, and gluten-free options all available so you can warm up with a hot drink and a tasty snack as you visit cozy local stores and gather the gourmet ingredients to make a lovely platter back in the comfort of your own home. Once you’ve put together your spread, enjoy some amazing games and conversation starters as well as additional activities and some special recommendations. Embrace the wonder of the season and we guarantee you’ll find a little winter magic at every stop!

Tickets and more information can be found here.

24. Enjoy a drag brunch with bottomless beermosas

There’s no better way to enjoy a weekend than with a brunch with friends, especially when entertainment is involved. Which is why the all-new Chicago Drag Brunches at Twisted Hippo offer the ultimate Sunday Funday! 

At Twisted Lemon’s Drag Brunches guests can choose from a range of delicious brunch options while enjoying 3 acts full of camp and sass starring Muffy Fishbasket and a rotating cast of Chicago’s Queens & Kings. 

More information and tickets can be found here.

25. Marvel at magic & music at Chicago’s newest speakeasy

If you head down to West Loop’s Grand Cabaret After Dark this month you’ll find a vintage evening of cabaret, jazz, and magic in Chicago’s newest speakeasy. Featuring live jazz music of classics and contemporary songs by the E-Line Organ Trio, and some mysterious magic by Mr. Jim Bergstrom! A delectable dinner and BYOB drinks rules ensure an all-round night of mystery and marvel.

Grab tickets to a Grand Cabaret experience here.

26. Attend an AirOtic Soireé cabaret dinner show

A number of fantastic burlesque shows offer an exhilarating night out in Chicago this year. Buckle up and prepare for a “Joy” ride at Chicago’s very own Joy District in River North! 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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27. 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.

28. Drink in a rooftop ski chalet

If you didn’t make it skiing this year and have missed out on those après ski vibes worry not because some little ski chalets have popped in Chicago and they are adorable. On a 3000-square-foot Wicker Park rooftop high above 1367 N Milwaukee Avenue, Whiskey Business has created a multifunctional space that will be running events throughout winter. Rooftop movie nights, weekend brunches, a curling rink, and MSU or Chicago Bears gameday packages offer something for everybody but it’s the ski chalets we’ve got our eyes on.

This year, the Wicker Park rooftop has some of the cutest little ski-chalets offering a cozy hideout for friends and family. The bar’s rooftop cabana huts have been decked out with fake fireplaces and alpine decorations so you can sink a few seasonal cocktails while snuggled up with your friends like you’ve just had a day out on the slopes!

More information can be found here.

29. Cool Off With Cocktails And Curling

If you’ve had enough snowglobes and hideaways for the season and are craving something competitive while socializing in style, The Gwen Hotel has the answer. You’ll find an array of igloos, firepits, and other outdoor dining spots all over Chicago but at The Gwen Hotel’s rooftop you’ll find a unique combination of curling and signature cocktails.

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.

30. Try a virtual whiskey tasting experience

If you’re not ready to go out and about just yet be it for the weather or the pandemic but are still keen to have a few drinks at home 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.

31. Cleanse your mind, body, and soul at L+A Healing Studio

Treat yourself to a soothing and revitalizing body treatment at L+A Healing Studio! L+A Healing Studio is a 21st-century new concept boutique and a leading therapy studio located in the South Loop. They combine massage, art therapy, acupuncture, yoga, and fitness – there’s something for everyone here. They strive to be a community of different ideas melded together and have combined their vast experience of massage therapy, jewelry-making, retail, western and eastern medicine training, art, dance, and fitness into a gathering place for the community so we can all heal together.

Tickets and more information can be found here.

32. Try out some virtual yoga and meditation classes

Image from Unsplash

We all need to chill after all the Christmas chaos, not to mention 2021 in general, and Wanderlust TV offers a way to do so from the comfort of your own home. Wanderlust TV provides live and pre-recorded yoga and meditation classes, DJ-mixed soundtracks, and enlightening talks. Bring expert teachers and speakers from Wanderlust’s festivals directly to your home virtually! 3-5 live yoga classes are held a day across multiple yoga genres. But Wanderlust TV is not just yoga — it also includes fitness, meditation, dance, sound baths, tarot & astrology, talks, & more. All to help you in your journey towards a healthy and inspired life!

More information can be found here.

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

If massages and meditation aren’t necessarily your thing but you wouldn’t turn down relaxing at a spa during these hostile months there is simply no better place than AIRE’s Ancient Baths. Located inside a historic River West factory restored to its original splendor you can now find optimum relaxation within the exposed brick, wooden beams, and industrial columns of the building. Inspired by the traditional Roman, Greek, and Ottoman ancient experience of bathing, there is nowhere offering more peace of mind in the Windy City.

34. Treat yourself to a beer bath

Another unique 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.

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. However, if you’re not one to recline in a bath and instead find your inner peace out and about surrounded by nature then heading out to the quiet of Illinois’ natural beauty is a great January. 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. Escape to a cabin in the woods

For an even more prolonged experience in nature. Getaway House is a chain of tiny cabin hideaways helping people in big, bustling cities like Chicago, DC, LA and NYC, disconnect from their busy city lives with restorative stays in the middle of nature. The city can at times become exhausting and we all need time to unplug ourselves from screens and technology, breathe fresh air and reconnect with nature.

Nestled in Grand Junction, Michigan, Getaway House’s stunning midwestern cabins are just a couple of hours away towards the beachside town of South Haven on the shores of Lake Michigan. With cabins with queens beds and queen-sized bunks spread out over 79-acres of beautiful forest, they are perfect for both romantic escapes and family adventures. They fully embrace the minimalistic lifestyle and all cabins feature floor-to-ceiling windows so you can wake up immersed in the wilderness.

More information can be found here.

37. Celebrate 100 years of the Morton Arboretum

Morton Arboretum- Autumn Foliage

Back in Chicago, the Morton Arboretum will this year celebrate its 100th birthday. To celebrate such an occasion, the 1,700-acre tree museum and research center is kicking off a yearlong centennial celebration building up to its 100th birthday. The popular Human+Nature exhibition will continue through March 2023 and two new large-scale sculptures and a commemorative centennial sculpture by artist Daniel Popper will be added to the exhibition in May bringing the total number of colossal sculptures to 8.

There will be events taking place at the Arboretum throughout the year including a dog admission day at the end of the month inviting members and guests the opportunity to visit the Arboretum with their dogs.

More information about the events taking place at the Morton Arboretum this month can be found here.

38. 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) are sharing their experiences with the iconic princess and her family throughout January 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.

39. 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.

40. Dine in total darkness with the Secret Society

If you missed it the first time round worry not because the ominous and delectable Dining In The Dark Experience is returning to Chicago in March. The mysterious secret society will be back at their residence in the 312 and quietly awaiting your attendance in total darkness. Combining a new mysterious plot and more culinary prowess, this enthralling dinner party is unlike any other and now each experience will come with a 5-course tasting menu and a welcome drink!

More information and tickets can be found here.

[Featured Image from Shutterstock]

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