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20 Awesome Activities For An Unforgettable January In Chicago

Elliot McGowan Elliot McGowan

20 Awesome Activities For An Unforgettable January In Chicago

It’s time to finally say goodbye to 2020, and welcome in 2021.

January is here marking the end of one of the most turbulent years in our recent history. We start off a year anew with renewed hope, the distribution of new vaccines, and a possible return to normality visible on the horizon. There are still some months to go, however, until we can safely resume the life we knew pre-2020, but that doesn’t mean we can’t enjoy a fun-packed January.

The Midwest’s icy winter is settling in but we’ve got a whole list of exciting things to do in the Windy City for those snow-lovers and winter-hibernators in equal measure. Here’s a list of 20 awesome activities for an unforgettable January in Chicago whether you’re a long-time local or an enthusiastic tourist.

1. Kick Back At OGs Heated Holiday Hideout

When indoor dining was first banned the popular Old Grounds Social in Lincoln Park quickly adapted by winterizing their outdoor space taking no half measures in the process. A new and improved heated patio is now hosting a series of January events to get us through the winter and OGs and Chef Josh Scheid are bringing back their sublime bottomless brunches. 2 hours of bottomless specialty winter cocktails, mimosas, and beers will be available with brunches every Saturday and Sunday providing the perfect way to clock out of our weekly responsibilities.

Truth be told you’ll struggle to find a day when there’s not something exciting happening at OGs. Trivia, Drag Bingo, and DJ Nights are taking place weekly all with complimentary specialty cocktails included. Enjoy a Holiday-Themed Trivia Night on Tuesdays, Holiday Drag Bingo on Thursdays, and live DJs every Friday and Saturday night.

2. Embrace The Chill At A West Loop Winter Pop Up

Another extraordinary winter escape can be found down in Fulton Market at Recess’s 14,500-square-foot patio. There you will find an amalgamation of interesting bars, food stands, and cabanas houses nestled within 30 shipping containers that create a truly unforgettable vibe. Recess has now revamped its patio offering a completely transformed West Loop winter pop-up and the perfect place to embrace the January chill. Ice sculptures and winter photo ops provide a feast for the eyes and the perfect Instagram material whilst fire pit tables, S’mores kits and boozy hot chocolates provide the perfect recipe to enjoy a toasty trip outside! Each ticket to Recess’s Fire & Ice Winter Pop Up gets you a Recess peanut butter boozy hot chocolate, a specialty cocktail, a S’mores kit and pretzel stick, and 1-hour admission to view ice sculptures & winter photo ops.

3. Jump Into 2021 With Indoor Skydiving

With every new year comes new dreams, new objectives, and fresh New Year’s resolutions. Of course; diets, workouts, quitting smoking, and the usual suspects will be encouraged even more so this year after the global pandemic further emphasized the importance of our health. But 2020 also reminded us that we should be active, try new things, and make the most of outdoor adventures and experiences available to us. One thing that always finds itself on bucket lists worldwide is skydiving.

Now, we’re not saying jump out of a plane in the freezing skies above Chicago, but we are saying give it a go in one of Chicago’s indoor centers to get a taste of what it is like and why it is such a popular ‘do before you die’ activity. With a state-of-the-art iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, Chicago is home to two conveniently located cutting-edge centers where kids and adults can get the same sensation you’d get 12,000 feet up in the sky. If the experience has you wanting more you can always test your vertigo above Chicago’s skyscrapers at one of the world’s largest skydiving resorts in Skydive Chicago and boast that you’ve jumped out of a plane above the Windy City.

4. Take To The Ice At Maggie Daley Park

Chicago's Maggie Daley Ice Rink

There’s no better way to glide into 2021 than with some winter skating. The ice skating ribbon at Maggie Daley Park is one of Chicago’s best winter-time activities. Experience “alpine in the city” skating down a quarter-mile winding ribbon of ice that curves up and down around a 40-foot climbing wall with the city’s stunning skyline in the backdrop. It’s a must for your winter bucket list. Reservations cost $5 for those who have skates and $16 for those who rent.

6. Check Out Joy District’s Winter Wonderland

With winter’s arrival in Chicago and the safety measures restricting indoor dining, we have turned to Chicago’s outdoor spaces for socializing and evening drinks. Usually, many of Chicago’s rooftops go into hibernation and wait out the cold but with the circumstances this year many have reinvented themselves to offer cozy ‘outdoor’ winter hideouts. Joy District’s rooftop is no doubt one of Chicago’s favorite rooftop escapes. Sparkling lights, comfortable patterned couches, and impeccable views of Chicago’s skyline create a stunning setting but it’s the magic of vibrant murals and cascading greenery that truly makes Joy District’s rooftop stick out from the rest.

Joy District’s Heated Winter Wonderland Rooftop And Holiday Cocktails offers an iconic winter experience where you can sip on mouthwatering cocktails on a warm rooftop while taking in the dazzling city lights with your quarantine crew. You can also rent a Rooftop Ski Lodge or a Rooftop Winter Igloo, but you’ll want to hurry as dates are filling up fast.

7. Cool Off With Cocktails And Curling

If you’ve had enough snowglobes 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 you’ll  The Gwen Hotel’s rooftop offers a unique combination of curling and signature cocktails.

The luxury hotel has kitted its rooftop out with not igloos, not ice skating, but an outdoor curling rink high in the sky. 45-minute curling sessions are $30 per person and come with a complimentary round of cocktails meaning you can sip away on your favorite tipple while battling your buddies.

8. 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!

9. Peruse Chicago’s Sublime Street Murals

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.

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 events of 2020 motivated many, many, astounding and poignant new murals. With coronavirus limiting our freedom, now is a great time to wrap up warm and hunt down the many street art masterpieces in our great city that prove Chicago’s art scene is legendary.

10. Discover West Town Street Art 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. 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. Over the years the B_Line has evolved into an idyllic place for unique individuals to congregate just off the beaten path. An immersive Chicago street art tour operated by a lively local guide is the best way to dive into the history of Chicago’s art scene. Tours of Fulton Market’s many murals promise passion and first-hand in-depth knowledge of the most remarkable murals and their inspiration.

11. Unleash Your Inner Street Artist

If all that street art’s got you feeling creative, at The Chicago Kedzie Plaza you’re invited to grab some spray paint and unleash your inner street artist on a 50ft mural! This interactive workshop will turn you into the artist and teach you all the steps along the way as you learn the ins and outs of working with spray paint and other elements of Urban Art. Not the most creatively inclined person? Have no fear, you’ll have two private instructors helping you out. Get your group together and create your very own painted mural!

12. Savor A Secret Food Tour In The Loop

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.

13. Host A BYOB Private Interactive Gameshow

In this fun-filled private event, you can enjoy a Black Mirror-esque modern-day gaming experience. Grab up to 8 of your friends and compete in video gaming across a cage-match setting to determine the ultimate winner. GUIX is your show, your games, and your friends with the fast-paced chaos of a cage-match battle! But that’s not all. The difficulties each team faces is controlled by the online audience. Anyone watching your show online will be able to vote during the live stream and influence what challenges and obstacles you and your friends face. GUIX is also BYOB so you can grab your buddies and some beer and let the games begin!

14. Unleash Your Inner Disc Jockey

2020 has given us plenty of time to learn something new and there’s still a lot of time to find new hobbies and discover new talents. Coronavirus restrictions have stopped many of us from visiting our favorite watering holes and evening haunts so why not start 2021 off with testing your disc jockey potential. Are you often trusted with the aux and often wow your friends with your musical wisdom? Lessons with Legends offers live, one-on-one sessions at PRYSM, a top nightclub in the world where you live out your DJ dreams and experience the adrenaline of musical stardom. Guests can select from a line-up of instructors including Gene Farris, DJ Heather, Anthony Attalla, and many more. The private sessions allow fans to feel the fervor of a festival headliner by pairing direct-guidance from pioneers of their craft while being on-stage and in-the-booth with state-of-the-art production and lighting.

15. Learn To Brew From Home

If you’re keen to learn a new skill but you’re more the type to sit and chat over a good beer than hit up a nightclub we’ve got you covered. Why not start the year off by understanding exactly what goes into your favorite tipple and learn a treasured skill in the process. The Live HomeBrew Experiencewill lead you through the process of brewing your own beer via live streaming with humor and history, from inside your own kitchen! They’ve curated the perfect kit for beginners with only the essential equipment to get the job done. Providing ease of use and safety, with minimum investment, shipped right to your door!

16. Enjoy A Speakeasy Cocktails & Burlesque Home Experience

We completely understand if heading outside isn’t appealing to you at the moment and we have a few at-home activities to keep you excited and entertained during Chicago’s chilly first months of 2021. With a Speakeasy Cocktails and Burlesque Experience, decadence is delivered to your door so you can enter a world where tipsy temptation awaits. This new entertainment-mixology experience delivers ten finely crafted cocktails to your door so you can sip away while watching electrifying performances. Featuring some of the top cirque, burlesque, illusion and theatrical performers in the world Speakeasy on Demand brings a naughty rendezvous to you and lets your imagination run wild.

17. Cleanse Your Body After Christmas Indulgence

Beer and cocktails aren’t the answer for everybody, of course, and if one of your New Year’s resolutions is to improve your diet and lifestyle a New Year’s Juice Cleanse and Unlimited Yoga Fitness Classes might be for you. South Loop’s L+A Healing Studio, a new concept therapy studio, combines massage, art therapy, acupuncture, yoga, and fitness to create a healing gathering place for the community. Unlimited yoga and fitness classes, massage therapy, and dance can be combined with jewelry-making, art-classes, and eastern medicine training to exercise your mind, body, and soul this January. Meanwhile, at Lincoln Park’s newest neighborhood Juice Bar you can try a 1, 2, or 3-day juice cleanse featuring nutrient-dense cold-pressed juices, whole-food health smoothies, and a menu crafted with natural and organic ingredients for the perfect post-workout meal that is proven to increase beneficial gut bacteria, promote weight loss and improve heart health.

18. Calm Your Mind With Meditation

We all need to chill after all the Christmas chaos, not to mention 2020 in general, and there’s nothing better for your soul than some meditation. If classes aren’t your thing, or you’d rather stay at home given the current circumstances, Wanderlust TV is your answer. Wanderlust TV offers live and pre-recorded yoga classes, meditation classes, and enlightening talks bringing 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. Wanderlust TV also includes fitness, meditation, dance, sound baths, tarot, astrology, and more.

Why not commit to meditation so you can find serenity, improve your quality of sleep, and make the most out of life with a one-year subscription that will grant you unlimited access to over 400 mindfulness sessions. One Year of Unlimited Meditation with Namatata was voted the best meditation app in 2020. It gives you access to over 400 themed sessions created with the help of doctors and psychologists to better manage your emotions and help you let go easily.

19. Take A Magical Journey

If you’re a tried and tested yoga veteran or just simply seek something a little different timeline healing is an intense guided meditation that aims to allow you to access a deeper connection with your past, future, and higher self. The workshop is approximately 1h 30 and combines shamanic journeying practices to guide you on a magical journey. The sessions are split between with time dedicated to the astrological energy of the week, guided meditations, and sharing mystical self-care practices.

If you want to take it a step further A Little Zen Box that includes crystals, candles, tarot cards, and at least 5 rituals to add to your wellness routines offers something to regularly look forward to and a new experience. Each month, curated items and instructions comprise A Little Zen Box that is sent to your door to help you with a monthly self-care routine. You can expect to try new items and learn new rituals all aimed at connecting you with your inner magic.

20. Book Tickets For The Little Mermaid-Themed Cocktail Bar

It’s always good to have something to look forward to and this unique mermaid cocktail party is a one-of-a-kind event. What are you willing to give up for the chance to drink with mermaids? Your voice, your heart’s desire… maybe your very own human form? Luckily, all your nautical fairytale dreams can come to life without having to sacrifice anything you hold dear to your heart. The Little Mermaid Cocktail Experience has plans of splashing its way to Chicago in March 2021, and you’re invited to witness this timeless tale like never before! Get your presale tickets here, and be the first to enjoy the iconic event!