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40 Magical Things To Do In Chicago This December

By Elliot McGowan

40 Magical Things To Do In Chicago This December

There’s snow place like Chicagoland.

Autumn has passed us by and the Midwest’s icy winter is now at our doorstep. More importantly, though, festive time in Chicago is in full swing and the turbulent year of 2020 is finally coming to an end. Make no mistake, winters can be as beautiful as they are brutal and despite the chilly weather and surreal situation we find ourselves in, there is still plenty to do.

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 that you can safely do from the comfort of your own home.

1. Take To The Ice At Maggie Daley Park!

Chicago's Maggie Daley Ice Rink

There’s no better way to glide into December 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 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 for your winter bucket list. Reservations cost $5 for those who have skates and $16 for those who rent, while the most sought-after dates like Christmas and New Year’s Eve will cost you $20.

2. Soar Around Rosemont’s Chicago Wolves Ice Rink

3. Make An Early Start On Christmas Shopping

4. Reserve An Igloo In The Sky

After a shopping spree, it’s time to sit back, relax, and sink a few much-needed drinks. Of all the magical outdoor dining options in Chicago, Joy District’s rooftop is an undisputed frontrunner. 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.

Rooftop Igloos and Rooftop Ski Lodges can now be rented, guaranteeing a unique evening beneath the Chicago stars and skyscrapers with your chosen quarantine crew.

5. Revel In A Rooftop Winter Wonderland

An equally stunning rooftop bar and igloos to boot can be found over at The Godfrey Hotel’s rooftop. Chicago’s largest indoor-outdoor rooftop with a retractable roof has the versatility to transform into any type of venue it desires. Luckily that means that retracting the roof officially makes it an outdoor space where fine dining and extraordinary views can be enjoyed. Heated igloos of various sizes have been erected for a winter wonderland that includes fire pits, fire dancing, live DJs, s’mores, and, of course, themed cocktails.

6. 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 only find curling and cocktails on The Gwen Hotel’s rooftop.

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.

7. Get Boozy With Peanut Butter Cup Spiked Hot Chocolates

Another unique Christmas activity can be had down at Recess’s Bar and Patio. An amazing winter wonderland has been created where you can capture some of your end-of-year festive memories!

Gather your besties, try the 12 Drinks of Blitzen, roast S’mores around one of the bonfire pits, and capture your holiday moments at the 6 different photo ops. You’ll even get a DIY cookie decorating kit, Recess Peanut Butter Cup spiked hot chocolate, and 1 Blitzen Cocktail all included in the entry fee! Happy Holidays!

8. Be Blown Away By Wrigleyville’s Santa Baby Pop-Up

Talking of Christmas pop-ups, few can rival Wrigleyville’s Santa Baby Pop-Up when it comes to decorations and extravagance. The immersive Christmas pop-up has once again taken over Deuce’s Major League Bar and covered a revamped patio head-to-toe and wall-to-wall with an exorbitant amount of Christmas decorations.

But it’s not just the surroundings that will have you stunned, the food and drinks are equally as impressive. Mega-Merry-Milkshakes like the “Red Velvet Cakeshake” and “Gingerman” are as colorful as they are tasty while you won’t want to share any of the cocktails on offer such as an Elf Fashioned,  a Merry Manhattan, nor a Jingle Juice. “Atomic Yule Logs” and “Christmas Dinner Sliders” round off the menu and we’ll let you discover exactly what goes into those sensational snacks yourself.

9. Hit Up A Hannukah-Themed Pop-Up

It’s not just Christmas pop-ups you’ll find in Wrigleyville. Back by popular demand, The Graystone Tavern has resurrected its “8 Crazy Nights” for 2020. 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.

10. Experience A Gorgeous Candlelight Concert

Of all the events happening in Chicago, few are as enchanting as the wildly popular Candlelight concert series. Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most unique locations. There are holiday dates throughout December offering both Jazz & Soul concerts, traditional classical music concerts, and your favorite festive classics. More info and tickets can be found here.

11-13. Head Down To OGs For A Snow Day Social

With indoor dining off the table, the popular Old Grounds Social in Lincoln Park has adapted to the times and surpassed our expectations. A new and improved heated patio hosting a series of events to get us through the winter, providing us all with a shining light in these trying times.

OGs and Chef Josh Scheid have long provided a unique weekend haven and a killer breakfast to boot. Thanks to the heated outdoor patio the bottomless brunches are back on and better than ever! 2 hours of sublime breakfasts, bottomless specialty holiday cocktails, mimosas, and beers will be available every Saturday and Sunday providing the perfect way to clock out of our weekly responsibilities and kick off a winter weekend the right way.

Brunches are far from the only thing taking place at OGs, however, every Saturday the heated patio will host a cozy cocktail event where everybody is encouraged to wear their most retro neon skiwear. Log cabin vibes in downtown Chicago is perfect for those Instagram snaps.

In all seriousness, you’ll struggle to find a day when there’s not something exciting happening at OGs. Holiday events are taking place throughout the week and all with complimentary specialty cocktails included. Holiday-Themed Trivia Nights on Tuesdays, Holiday Drag Bingo on Thursdays,live DJs every Friday and Saturday night  ensure a season of holiday fun to get us through the winter.

14. Test Your Luck With Forbidden Online Bingo

If bingo is your thing but you’d rather sit safely and comfortably at home, worry not, we’ve got the answers. Here is your opportunity to have some fun with a live, online version of bingo where you’ll get to socialize and make new friends from the safety and comfort of your home. Play DJ Rockstar Aaron’s original Forbidden Bingo Online Party from anywhere. Receive a complimentary gift and win naughty prizes while playing bingo with a twist!

15. Escape Reality With A Private VR Party

Get your family or quarantine crew off the couch with private gaming at Redline Virtual Reality. Private packages guarantee one hour of totally private playing time for just one hundred dollars. You’ll be the only ones in the building! Redline VR has packages perfect for kids seven and up, and others with plenty of zombies. Plus, parties can do premiere escape rooms completely in virtual reality!

16. Enjoy A Chilled Rooftop Movie Night

Whiskey Business has created the perfect movie night set up on its Wicker Park rooftop so you can continue those beloved movie nights with friends or family while feasting on some sublime snacks and fantastic beverages. On specific nights of December, Christmas classics will be shown on two 120-inch screens at the 3,000-square-foot rooftop drinking haven turning it into a cozy cinema-viewing theater. There will be showings of popular festive flicks like ElfBad Santa, and It’s A Wonderful Life.

17-21. Check Out Chicago’s Light Shows

Morton Arboretum Illuminations 2020- Drive Through

Let there be light! While many parts of Illinois have closed down due to Covid-19 health and safety restrictions Chicago’s annual outdoor light shows are one of the few beloved seasonal events that have been largely unaffected. Every year more dazzling light shows pop up in extraordinary locations around Chicago. Gorgeous natural backdrops, cutting-edge light art installations, and festive cheer all combine this December in some magical multi-sensory events like no other.

  • After a complete sell-out in its debut season, Chicago Botanic Garden’s Lightscape returns through January 3, 2021.
  • Illumination: Tree Lights at The Morton Arboretum will feature unique light displays and a customized soundtrack in the nonprofit public garden and outdoor museum through January 3, 2021.
  • Following its phenomenal 25th anniversary last year, Lincoln Park Zoo returns with a stunning array of light displays for Zoolights 2020. There will be four free days on December 9, 17, 21, and 29. The enchanting annual event will run through January 3, 2021.
  • Let It Shine is taking place not far from Chicago Botanic Garden at North Shore’s Northbrook Court. Claiming to be the largest drive-thru light show guests are invited to drive through an immense wonderland of dazzling archways, glowing snowmen, and more through January 9, 2021.
  • Lincoln Park Zoo isn’t the only zoo in Illinois throwing a party of lights. It will be Brookfield Zoo’s 39th year making Holiday Magic Chicagoland’s largest and longest-running lights festival. Holiday magic will feature over a million twinkling LED lights, a giant 20-foot-lit orb ideal for Instagram selfies and holiday photos, a 600-foot-long light and music tunnel, and, of course, a stunning 41-foot-tall tree to celebrate the holidays. Holiday Magic finishes on December 31, 2020!

22. Keep An Eye Out For The CTA Train

Of all the dazzling lights that glisten around Chicago during the winter season, there is one that is more eagerly anticipated than others, and that’s because it features Santa himself. 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.

Though this year the CTA Holiday Train will be “out of service” with no passengers in order to keep the event safe and socially distanced. Santa and his elves will still be showing up all across Chicago with Santa and his reindeer upfront in his open-air sleigh so excited onlookers can still safely greet Santa from afar! The holiday train will travel all 8 lines through December 21. More information can be found on the Chicago Transit Authority’s website.

23-24. Don’t Miss December’s Astounding Astronomical Spectacles

With the great variety ofmagical light shows that winter brings, it’s easy to forget that the sky provides some stunning celestial light shows of its own. Aspiring astronomers will know that the blazing fireballs of the Leonid Meteor Shower last month were only a warm-up to an even more incredible meteor shower that takes place in December.

  • The Geminid Meteor Shower usually occurs from around December 4 until December 16. This year it is expected to peak after nightfall on Sunday, December 13, and into dawn on Monday, December 14, with the optimum time to look to the skies said to be around 2 am. This year astronomers have predicted that the Geminids will bring up to 150 visible meteors per hour and luckily, with a New Moon expected around December 14th, the extra-dark skies will help illuminate the stars and meteors.
  • The second great astronomical event of December is the “great conjunction” when the two gas giants, Jupiter and Saturn, align. The two planets will come extremely close to one another on Monday, December 21, and shine brightly as a “double planet.” The orbits of Earth, Jupiter, and Saturn cause this phenomenon to happen once every 20 years. But to find the last time the planets were this close together in the night sky you’ll have to look all the way back to medieval times nearly 800 years ago, on March 4, 1226.

25. Admire The Art On The MART Visuals

A light show of a sort, and absolutely free, Art On The MART, is certainly a spectacle to behold. Having fired up all 34 digital projectors Art On The MART once again breathes life into the 25-story-tall face of the Merchandise Mart. Projections are displaying an all-new program that knits together dynamic moving images with a unique soundscape. The 30-minute shows feature a debut of The Joffrey Ballet’s The Nutcracker accompanied by the famous score from Tchaikovsky and works from the Art Institute of Chicago’s exhibitions “Monet and Chicago” and “Bisa Butler: Portraits”.

There will also be a debut of “City Circle Heart” from local nonprofit Arts of Life which features moving images created by five artists with physical and intellectual disabilities. Art On The Mart takes place each night at 7:00 pm and 7:30 pm through Wednesday, December 30, 2020.

26. Peruse The Magnificent Street Murals Of Chicago

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 2020 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.

With coronavirus limiting our freedom, now is a great time to wrap up warm and hunt down the many masterpieces in our great city created by both notable artists and up-and-coming talent.

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. 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!

29. 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. On this 3-hour tour of Chicago’s food scene, you’ll see what sets this friendly mid-western metropolis apart.

On this tour, 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. Really appreciate how important the immigrants that built this town are to the food scene.

30. Take A Trip Through Time With A Gangsters And Ghosts Tour

Chicago has a more fascinating history than even its mesmeric mix of architecture depicts. Any 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. The Gangsters And Ghosts tour 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!

31. Explore The Most Instagrammable Locations Of Chicago

Looking for a mix of everything but especially photo opportunities? This Chicago Walking Instagram Tour is for those who want a little bit of culture, some amazing architecture, and plenty of photo opportunities at the most Instagrammable spots in Chicago. After meeting your friendly local guide at a designated meeting point you will begin a day walking throughout Chicago and exploring the most famous locations in the city. The tour is fully packed with famous landmarks, vintage architecture, secret spots, romantic locations, and much much more!

32. Discover The Love Stories of Chicago

If the mention of romantic spots has piqued your interest and you’re looking for a unique date, this exclusive tour is perfect for all the romantics of the world! Together with the professional local guide, you will visit the most romantic places in the city and learn of the best places for dates in the city and where to take the most romantic photos. You will be surprised how many historical love stories are hidden in the streets, buildings, parks of the city. From heartbreaking and tragic tales to hilarious and spicy anecdotes.

33. Attend The World’s Largest Virtual Speed Dating Event

Don’t have a partner to accompany you on a romantic date? Worry not. The most magical time of the year is also the most romantic and this year the largest online singles event in the world is taking place on Christmas Eve – brought to you by the one and only Matzoball!

They’ve been hooking singles up since 1987! Don’t let Covid stop you from meeting your soulmate, because on December 24th they could just be a click away. Get dressed up and join the virtual speed dating experience for a night filled with the hottest singles in Chicago!

34. Learn To Brew From Home

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 bars and watering holes for some time. While things look like they will improve in 2021 there’s no time better to learn a new skill, and why not start with understanding exactly what goes into your favorite tipple.

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!

35-36. Calm Your Mind With Meditation And Magic!

Beer isn’t the answer for everybody, of course, and if all the Christmas chaos is getting to you, not to mention 2020 in general, there’s nothing better for your soul than some meditation. Let go of stress and anxiety and connect with the now.

  • Timeline healing is an intense guided meditation that will allow you to access a deeper connection with your past, future, and higher selves. The meditation and magic workshop is approximately 1h 30 starting at 6 pm EST on Fridays. Shereen combines shamanic journeying practices to guide you on a magical journey. There is a lot we cannot control at the moment, but one thing we can is our ability to access our inner magic.
  • If you’d rather discover your best self at your own pace and whenever it suits, Wanderlust TV is your answer. Wanderlust TV offers live and pre-recorded yoga classes, meditation classes, 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. Wanderlust TV also includes fitness, meditation, dance, sound baths, tarot & astrology, and more. All to help you in your journey towards a healthy and inspired life!

37. Give Your Hand A Go At Palmistry 101

Talking of a deeper connection with your past, future, and higher selves, few people foresaw the tumultuous ride that 2020 provided. It is most certainly a year we want to put behind us and instead, look ahead to pastures new. So what if you could peek behind the curtain and look into 2021 and beyond? What if a detailed analysis of the topography of your own hands could offer an esoteric glimpse into the unknown?

A new interactive experience known as Palmistry 101 invites you to discover the art of palmistry from the safety of your own home. With the virtual guidance of an expert, you can learn how to interpret the complex network of lines and contours that make up your own palm.

Whether you’re convinced you’ve inherited a third eye or you just want to develop a new party trick, this interactive event is a one-of-a-kind experience that can be enjoyed for just $10 on any Wednesday, Thursday, or Friday night throughout December.

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

Regardless of what your future holds it’s always good to have something to look forward to and this 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 get your hands on tickets!

39. Be Ahead Of The Chicago Crowd

We’ll also let you in on a little Chicago secret. With all the igloos being erected around Chicago their magic will soon be lost in the wind and businesses are striving to create something unique. What if we told you that an igloo village where each igloo has been customized by talented local artists is in the works?

Imagine. The snow beats down outside as the Midwest’s winter breezes mercilessly through Chicago. A numbing chill fills the air and ice cloaks the curb but inside a prismatic urbanized arctic igloo, you find you and your chosen accomplices snug and well-fed, each clutching your favorite cocktail. This is what awaits you down at HVAC’s Winter Igloo Dining & Drinks Experience, where you will find a fantastic fusion of Chicago’s revered art and gastronomy scenes, not to mention the potential for some iconic Instagram moments. The eye-catching collection of cozy winterproof domes is in the works, and you can be a trailblazer by reserving an artist’s igloo long before the secret sweeps through Chicago.

40. Look Beyond Winter

2021 will hopefully be a far better year than 2020. With a vaccine on the horizon, fingers crossed, it looks as though life will gradually return to the normality we were used to before the global pandemic. We’re all dying for an escape but it’s unclear when in 2021 holidays and international travel will once again be allowed. Luckily, a luxurious Illinois answer has presented itself.

Camp Aramoni is a first-of-its-kind brand new luxury campground in Illinois. The 96-acre space has been work-in-progress for a few years and will finally open in spring. Guests can expect a five-star luxury experience in a natural paradise where disconnecting is easy with hiking trails, yoga, boozy picnics, and other on-site activities along the lush Vermillion River. Famed chef Cleetus Friedman has officially joined the Camp Aramoni team meaning the secluded natural valley offers luxury living in lavish safari-style tents and now also world-class cuisine.