28 Splendid Things To Do In Chicago During December

Charli Renken Charli Renken

28 Splendid Things To Do In Chicago During December

December in Chicago is cold AF, but that doesn’t mean we can’t have any fun!

December might come with chilly weather, but it also brings some incredible events and things to do with it. Here’s a list of _ things we think are worth braving the cold for.

1-12 Enjoy these twinkling holiday lights.

Photo: @ohheyloljaykay

One of our favorite things to do in Chicago during the winter is to experience all the magical holiday lights the city has to offer. Check out our guide to Chicago’s holiday lights here.


13. Get a unique gift for someone special at the Chicago Artisan Market, Dec 1.

If you’ve started looking for holiday gifts, we have the perfect place to find something truly unique. The Chicago Artisan Market features the Midwest’s best food, fashion, home decor, and art. The market is filled with incredible small businesses whose products are guaranteed to wow those on your gift shopping list this year. Get tickets now!


14. Eat boozy donuts at Chicago’s first Hanukkah Pop-Up Bar, 8 Crazy Nights, opening Dec 1.

Photo courtesy of 8 Crazy Nights.

If you’ve been wondering where the Hanukkah bar is in Chicago’s craze of Christmas pop-ups, we have some good news. Finally, a festive Hanukkah-themed pop-up bar named 8 Crazy Nights is opening at the Graystone Tavern in Wrigleyville next month. Mazel tov!


15. Attend a hysterical performance of The Buttcracker.

Photo by Karmen Elaine.

The Buttcracker: A Nutcracker Burlesque returns to the Den Theatre Dec 5 for a fourth year of Christmas-themed debauchery. A sexy twist on the classic tale, the live performance is filled with burlesque, magic, sword balancing, circus, dance, and more! Tickets for this raunchy, holiday spectacle are on sale now.


16. Stroll through a winter wonderland at Winter Wonderfest, Dec 6.

Winter Wondertown
Photo: Navy Pier

If you’re looking for thrills without the chills this holiday season, Fifth Third Bank Winter Wonderfest promises exactly that, with a forest of 500 trees decorated with 25,000 ornaments to enjoy. There’ll be over 20 rides and attractions to experience, including the new-for-2019 ‘Wind Chill’, which promises to take visitors soaring 50 feet above the central Festival Hall.

If you prefer your Christmas turned down a few notches, Winter Wonderfest hosts a ‘sensory-friendly’ version as well. More information. 


17. Start the Holidays off right with a full glass at the Chicago Wine Fest, Dec 7.

Indulge your senses by sampling premium varietals from some of Chicago’s best wineries, eat delicious food, and enjoy live musical performances. Featured wineries include PRP Wine International, Fenn Valley Vineyards, Vin 312 Winery, Rosé Bubbles and more! Get 35% off VIP tickets here!


18. Or enjoy your booze at Zoolights as part of the Ugly Christmas Sweater & Holiday Lights Bar Crawl, Dec 7.

If you love ugly Christmas sweaters and watching holiday lights, we’ve got the perfect bar crawl for you. Coming to Chicago Dec 7 is the Ugly Christmas Sweater and Holiday Lights Bar Crawl! Pull on your favorite ugly holiday sweater and experience Zoolights in Lincoln Park for this year’s boozy Christmas crawl. Tickets are on sale now!


19. Party for an important cause at the Unicorn Ball, Dec 13.

Photo: @colectivomultipolar

The Trans Liberation Collective will host its 3rd annual Unicorn Ball fundraiser at the Brave Space Alliance. People of all identities and gender expressions are welcome to drink, dance, eat and enjoy a number of fun performances! Proceeds go to the Brace Space Alliance and Trans Liberation Collective. More information.


20. Hit all the best bars in Wrigleyville during TBOX’s 24th Annual Twelve Bars of Xmas bar crawl and costume party.

Photo courtesy of TBOX

TBOX throws the largest, longest-running Christmas bar crawl in Chicago. This year kicks off with live music from Hairbanger’s Ball at 9 a.m. and continues all day, visiting some of the best bars in Wrigleyville. Tickets include free breakfast, $12 gift cards, great drink specials, TBOX swag, and much more festive fun! TBOX is Chicago’s best costume party and Christmas celebration. Don’t miss it on Dec 14. More information.


21. Enjoy the magic of classical music by Candlelight, Dec 18 and 19.

Coming to Chicago in Dec is Candlelight, a stunning performance of classical music by twinkling candlelight. Tickets to the first show, which features Vivaldi’s Four Seasons, are sold out, but you can still get tickets for Candlelight’s holiday special, Dec 19. Buy tickets here.


22. Eat incredible German food or find the perfect gift at the Christkindlemarket.

Photo: @pedrazaa

If you’re still looking for that perfect gift or have the munchies for sausages, pretzels, or German chocolate, look no further than the Christkindlmarket. The unique German fair comes to Chicago every year to spark joy for thousands of Chicagoans (we may have gone twice already.) Check out our complete guide of everything you need to know about this classic Chicago tradition.


23. Toast with fellow rebels at the Anarchist Tea, Dec 21

Photo: Pixabay

The PO Box Collective hosts a monthly social gathering for anarchists, abolitionists, anti-capitalists and like-minded folk. Practice some activist self-care with various teas, coffee, and vegan snacks. Attendees are encouraged to bring something delicious to share. More information.


23. Bring home a plant buddy at the Plant Shop Pop-Up, Dec 22

Photo: Pixabay

Bring home a new plant (or two, or three, or… okay, fine, we’ll put one back) at the Plant Shop Chicago Pop-Up. Most of the plants will be hard-to-kill cacti, so if you don’t exactly have a green thumb, that’s okay! There’s a plant for everyone. Chicago artist Bird Milk (Diego Aguilar) will also be painting clay pots for you to take your new plant friend home in! More information.


24. Try curling on Whiskey Business’ rooftop all month long.

Photo: Whiskey Business

Always wanted to try the popular winter sport of curling? Love hot chocolate and rooftop bars? Check out Whiskey Business’ Rooftop Curling! You can learn a new sport (or ice them competition if you’re an old pro) and enjoy one of Chicago’s best rooftop bars. More information.


25. Get cultured for free at the Art Institute of Chicago, Dec 26

Photo: @onthe.bl

Museums can be expensive to visit, but luckily many Chicago’s have free admission days. The Art Insitute offers free admission to Illinois residents Dec 26. Relax after the holidays by taking a walk through one of Chicago’s finest art collections. More information.


26. Crawl ‘Til the Ball Falls at this Chicago NYE Bar Crawl, Dec 31.

This is a bar crawl like no other. Celebrate 2019’s best moments and kick off 2020 with a golden ticket to some of Chicago’s best bars. Your bar crawl wristband gets you free entrance into any of the participating bars as well as special drink prices like $4 beers, $5 well mixed drinks, and $6 shots! More information. 


27. Make your 2020 goals count at the Annual Resolution Gala, Dec 31.

Ring in the new year in style at the 8th Annual Resolution Gala at The Aon Grand Ballroom. This incredible party has 30 bars, a bountiful buffet, superb DJs, and a spectacular fireworks show over Lake Michigan! Dance all night and toast to the new year with champagne at midnight. Happy New Year, indeed! Buy tickets here.


28. Attend any of these other epic NYE parties to end the decade.

Photo: Shutterstock

Chicago’s NYE scene is enormous! We’ve put together a guide of all the best parties, performances, and firework displays worth going to. Check it out here!

Looking for more festive celebrations? Check out our guide to things to do over the holidays in Chicago for more inspiration.

Photo by Bryan Rodriguez on Unsplash.

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