25 Exceptionally Jolly Ways to Celebrate The Holidays In Chicago

Charli Renken Charli Renken

25 Exceptionally Jolly Ways to Celebrate The Holidays In Chicago

Get into the holiday spirit with these festive events, restaurants, and things to do in Chicago!

Dec is just around the corner and with it comes a myriad of holiday festivities. We know it’s not even Thanksgiving yet, but it’s never to early to put the holidays on your calendar. Here’s our list of things to do in Chicago this holiday season. (Our favorite has to be Zoolights, though.)


1. See Santa early at Chicago’s Thanksgiving Day Parade

Photo: @michele.marvin

Chicago’s Thanksgiving Day Parade always has a little sneak peek of Santa. Kick-off your holiday festivities by watching the parade to celebrate Thanksgiving, then launching right into Christmas as Santa’s sleigh floats down State St. Check out our full guide to the parade here. 


2. Experience spectacular Christmas lights at these popular viewing locations.

Here at Secret Chicago, we love this time of year when Christmas lights start to go up around the city. The dazzling lights are so beautiful against Chicago snow. It makes us feel all warm and fuzzy inside. Here are 12 of our favorite spots to see Christmas lights in Chicago. (Spoiler: Zoolights is our top pick)


3-9. Have a festive drink at one of these holiday pop-up bars.

Photo: @christmasclubchicago

There’s seems to be a new holiday bar popping up every day in Chicago this season. Have a drink and enjoy the festivities at any of these jolly pop-up bars.

3. The Christmas Club at the Country Club, 3462 N Clark St, Chicago, IL
4. Winter Wonderland Rooftop Igloos at Joy District, 112 W Hubbard St, Chicago, IL
5. Santa Baby Christmas Bar, 3505 N Clark St, Chicago, IL
6. Elf’d Up at Deuces and The Diamond, 3485 N Clark St, Chicago, IL
7. Frosty’s Christmas Bar, 809 W Evergreen Ave, Chicago, IL
8. 8 Crazy Nights Hanukkah Bar at Graystone Tavern, 3441 N Sheffield Ave, Chicago, IL
9. Reindeer Room at Tack Room, 1807 S. Allport, Chicago, IL


10. Catch a showing of The Buttcracker: A Nutcracker Burlesque for a hilariously jolly time.

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.


11. Wear your ugliest sweater to Chicago’s Ugly Christmas Sweater and Holiday Lights Crawl

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!


12. Or hit all the best Wrigleyville bars at TBOX’s 24th Annual Twelve Bars of Xmas.

Photo courtesy of TBOX

TBOX throws the largest, longest-running bar crawl in Chicago. This year kicks off with 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!

The theme this year is memes, so come dressed up as your favorite internet sensation. Twelve Bars of Xmas is Chicago’s best costume party and Christmas celebration. Don’t miss it on Dec 14. More information.

13. Listen to Holiday classics by candlelight at the Newberry Library.

Experience an intimate holiday concert hosted by Candlelight, Chicago’s newest classical music series. Just in time for the holidays, Candlelight is performing a special holiday show featuring the Metropolis String Quartet and music by Vivaldi, Mozart, Bach and more. Tickets are selling fast, though, so act fast. More information.


14. Create your own granite Menorah over drinks at the Chabad Jewish Center of the South Loop.

Photo: Chabad Jewish Center of South Loop

Prepare for Hanukkah with the Chabad Jewish Center of the South Loop’s Menorahs and Martinis event at NEMA Chicago. This event will teach you how to create and decorate your own granite Menorah while socializing over delicious cocktails. The decoration begins Dec 8 at 7:30 p.m. More information. 


15. Celebrate the first night of Hanukkah at the West Lakeview Manorah Lighting.

Image by kevindvt from Pixabay

Head to Lakeview Dec 2 at 6:30 p.m. for the lighting of a community Menorah. The lighting will take place outside at the Lincoln Hub intersection of Lincoln/Southport/Wellington. Afterward, enjoy music, games and traditional food at Golden Apple Restaurant. More information. 


16. Go Caroling at Cloud Gate (AKA The Bean)


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Bundle up and head downtown for a holiday part concert, part sing-a-long. Gather in front of the Cloud Gate sculpture (AKA The Bean) in Millennium Park and listen to a talented choir perform holiday classics and join in with songbooks provided at the event. Caroling will take place Fri Nov 29 – Dec 20. More information.


 17. Find the perfect gift at the Christkindlmarket.

Photo: @chicagodiaries20

As Dec quickly approaches, now’s a good time to start gift shopping. There’s nowhere better to get a handmade, unique present than the Christkindlmarket, a popular German fair that comes to Chicago every winter. Check out our complete guide of everything you need to know about this classic Chicago tradition.


18. Celebrate St. Lucia Festival of Lights in Andersonville.

Photo courtesy of the Andersonville Chamber of Commerce.

For those of you who are more inclined to celebrate the Winter Solstice than Christmas, the St. Lucia Festival of Lights in Andersonville is a great, illuminated event. While the St. Lucia festival is a relatively modern tradition in Sweden, it’s incredibly popular and with a large Swedish community in the city, it’s no wonder Chicago celebrates. The event begins Dec 13 at 4:45 p.m. with a torch-lit procession lead by specially chosen “Lucia girls” in long white robes. Afterward, participants are invited to a celebration at the Chicago Waldorf School. More information.


19. Celebrate Yule with the Covenant of Earth and Sky

Photo: Covenant of Earth and Sky – CUUPS Chapter

Another festive occasion for the Winter Solstice, the Covenant of Earth and Sky (COVES) will host a Yule ritual and celebration Dec 22. Come together at the Second Unitarian Church of Chicago to embrace winter and celebrate renewal, peace, re-birth, and inter-connectedness. COVES is a multidenominational Pagan-based group, but all are welcome to join in the festivities. More information.



20. Walk through a wonderland of snow at the Winter Wonderfest.

Photo: Navy Pier

If you’re looking for thrills without the chills this holiday season, the Fifth Third Bank Winter Wonderfest promises exactly that, with a forest of 500 trees decorated with 25,000 Christmas ornaments to enjoy. Check out our guide here.

For those of you looking for a quieter Christmas stroll, the festival also has a sensory-friendly day where things are turned down a bit. More information here.


21. Experience holidays internationally at Christmas Around the World & Holidays of Light at the Museum of Science and Industry.

Photo: @bunmi_ishola

What began with one single tree has exploded into a four-story celebration of holiday lights. The Grand tree in the center is surrounded by a forest of more than 50 other trees decorated with glittering lights and ornaments. Displays representing holiday traditions from cultures around the world are decorated by volunteers every year, and on the weekend visitors can enjoy live performances. Go international with your Christmas lights viewing at the Museum of Science and Industry. More information.


22. Ride the CTA Holiday Train & Bus

Photo: @bushelled

Possibly the most Chicago of Christmas lights events, the CTA Holiday Train & Bus brings the spirit of the holidays to thousands of riders every year. With two festively decorate trains and a bus, CTA holiday transit serves two very important purposes: to get Chicagoans hyped up for the season and also to deliver food to various charities throughout the city. Santa waves boarding riders onto the train from his sleigh (open-air flatcar) carrying his reindeer and holiday trees. The holiday transit service starts Nov 29 and ends Dec 23. Find the full holiday transit schedule and more information here.


23. Watch the Wreathing of the Lions at the Art Institute of Chicago.

Photo: @onthe.bl

The day after Thanksgiving, the Art Institute places wreaths around the necks of their famous lion statues. The Gay Men’s Chorus leads a celebration at the museum steps for the special occasion and everyone in attendance gets free hot chocolate! More information.


24. Take part in or cheer from the sidelines at the Santa Speedo Run in Boystown.

Possibly one of the silliest of Christmas events, the Santa Speedo Run is an annual one mile run through Boystown in which runners can only wear a Santa’s hat and speedo. Entrance is a suggested $25 donation to the Center on Halstead, an LGBTQ+ community center. Santa Speedo Run will take place Dec 7 at 12 p.m. More information.


25. Dine at the Walnut Room under the Great Tree at Macy’s

Photo: @ohheyloljaykay

The Walnut Room at Macy’s on N State St. is known for its spectacular holiday decor. The restaurant has a giant, 45-foot Great Tree and a special holiday menu that can’t be beat. Celebrate Christmas in style by booking a reservation any time in Nov through early Jan. More information. 


Find more festive ways to celebrate on the Fever app. 

Feature photo by Jill Wellington from Pixabay.

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