31 of the Best Things to Do in Chicago and the Suburbs This December

This December, prepare to celebrate the best Chicago and its suburbs have to offer, as the weather gets colder and 2022 draws closer. Whether it’s a holiday-themed performance or a chance to learn something new, you won’t struggle to find something to do this holiday season. Here are 31 of the best things to do and see in Chicago and the suburbs this December.

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All Month Long

Lost in Lake Forest Suite Experience at the Deer Path Inn

255 East Illinois Rd., Lake Forest

Courtesy of Deer Path Inn

“Home Alone” fans, this is for you! Book a night at Lake Forest’s Deer Path Inn in their holiday “Lost in Lake Forest” suite, complete with pizza, the classic holiday film, and souvenir robes. Room service will also deliver local candy, boozy milkshakes and you even go home with gift cards to local stores. Thru Jan. 2, 2022.

Luft Balloons: Santa Wonderland Immersive Holiday Experience

2300 W. Fullerton, Chicago

Photo courtesy of Luft Balloon Store

Luft Balloons Santa Wonderland experience has returned in their new location. The immersive experience will run until Dec. 23. “At Luft Balloons, we are known for creating big and bold balloon displays at our showroom and all across the city,” said Elaine Frei, founder of Luft Balloons. “The holidays are no exception, and our new and improved location allows us the space to get over-the-top creative!”

WNDR Museum Celebrates Holiday Season with “Winter WNDRland” Experience

1130 W. Monroe St. Chicago

WNDR Museum, photo courtesy of Time Out

Beginning Nov. 27 and ending Jan. 2, Chicago’s original immersive art and technology experience is inviting guests to experience the holiday spirit at its inaugural Winter WNDRland event. “WNDR Museum is founded on inspiring childlike joy and curiosity within us all, and nothing has the power to bring us back to that quite like the holidays,” said Ryan Kunkel, president of WNDR Global. “Whether enjoying a cocktail at our Ugly Sweater Party or indulging in holiday treats at WNDRland of the Sweets, Winter WNDRland will be a festive experience for families, date nights and anyone seeking holiday cheer.”

Willow Hill Winter Magic Drive-Thru Christmas Lights

1350 Willow Rd, Northbrook

Willow Hill Golf Course will be hosting its first Christmas lights event right in Northbrook. Beginning Nov. 20 and ending on Jan 2, families can witness millions of beautiful lights from 4:30 pm to 10:30 pm. 

Chicago’s Historic Medinah Temple Transformed into Immersive Artist-Driven Holiday Experience

Medinah Temple, photo by John J. Kim

From Dec. 2 to Jan. 3, the Medinah Temple will be introducing Sleigh Bells—a trippy and immersive holiday pop-up full of color, sound, technology, art and Christmas spirit. Produced by Superfrüit, this event will be a unique and interactive experience for all. “Chicago is home to a variety of Christmas markets, holiday themed bars and pop-ups, but we wanted to present a totally unique experience that stands out from the rest by using lighting, technology, projection and art to put the spotlight on local Chicago culture,” says Superfrüit’s John Schroeder.

You’re a Good Man, Charlie Brown

300 S. Waukegan Road, Lake Forest

The Citadel Theatre will be hosting the live performance of “You’re a Good Man, Charlie Brown”. The play, according to Choose Chicago, is about Charlie Brown and the Peanuts gang exploring “(…) life’s great questions as they play baseball, struggle with homework, sing songs, swoon over their crushes, and celebrate the joy of friendship.” 

Pet Nights with Santa

220 Fashion Outlets Way, Rosemont

The Fashion Outlets of Chicago are inviting all pet owners to celebrate the holiday season with their furry friends. Every Monday from Nov. 29 to Dec. 20, from 6:00 to 8:00 pm, dog owners can get their dogs a photo with Santa. 

Game of Gnomes Scavenger Hunt

Downtown Wilmette is looking for the best seekers to participate in their weekly Game of Gnomes event. Participants will look in storefronts for 12 total gnomes for a chance to win a Shop Wilmette gift card.

Oil Lamp Theater Presents It’s a Wonderful Life

1723 Glenview Rd, Glenview

Photo courtesy of Chicago Plays

Prepare to enjoy the magic of this holiday classic. From now until Dec. 30, Oil Lamp Theater is reopening its doors for a live-action performance of It’s a Wonderful Life: A Live Radio Play in Glenview. 

‘Twas the Night Before… by Cirque du Soleil

175 N State St

This December, secure a set of tickets to The Chicago Theatre to watch Cirque du Soleil perform ‘Twas the Night Before…”. Tickets are now on sale and performances are happening all month long. 

Big Time Rush in Chicago

175 N State St

American pop band Big Time Rush is back and heading to the Chicago Theatre on Wednesday, Dec 15. The band consists of Kendall Schmidt, James Maslow, Carlos Pena Jr. and Logan Henderson. Originally the group aired on a popular self-titled Nickelodeon TV show, but now they’ve reunited for the first time in years. 

Dec. 1: Holiday Jazz Dinner

619 Howard St., Evanston

The Palmhouse

The Palmhouse in Evanston would like to invite guests for a Holiday Jazz dinner, as they work together with Rogers Park’s Le Piano. The event will occur from 7:00 pm to 9:00 pm, as people will enjoy a night of music and French-inspired meals. 

Dec. 2, 9, 16: Holiday Sewing Workshop

400 E Illinois Rd, Lake Forest

This sewing class is for anyone of any skill level, as people can “Get holiday-ready during this three-week sewing workshop. Students will make a holiday-themed project and will be able to give it as a gift to a friend, family member or keep it for themselves.” The event will occur on Dec. 2, 9, and 16 from 5:00-6:00 pm

Dec. 2-5: One of a Kind Holiday Show 

222 W. Merchandise Mart Plaza, Chicago

Considered Chicago’s most beloved holiday event, the official return of the One of A Kind Holiday Show is here. This event will feature 400 talented artists, artisans and makers from across North America. From fine art to handmade goods, gourmet cafes, bar areas and live entertainment, the One of a Kind Holiday Show will be celebrating its 20th anniversary this year. 

Dec. 3: Winnetka’s Annual Tree Lighting

541 Birch St., Winnetka

2018 Winnetka Tree Lighting

From 4:00 to 6:00 pm, the residents at Dwyer Park will have their annual event. Guests will be able to enjoy choir music, admire the beautiful tree lighting and enjoy a warm cup of hot chocolate. 

Dec. 3: Kids Only Holiday Shop

400 E Illinois Rd, Lake Forest

The Gorton Community Center will be hosting a kids-only holiday shop. From 2:00 pm to 6:00 pm, kids ages four to 10 will have a chance to be an independent shopper. Local vendors and artisans will be around with discounted items. 

Dec. 3-5: PASTA Peter Pan Performance

400 E Illinois Rd, Lake Forest

Nancy Hughes Theatre at Gorton Community Center

The Gorton Community Center is hosting a live performance of Peter Pan! “This superb musical adaptation captures all the magic and charm of Peter Pan.” 

Dec. 4: 3rd Annual Elf Invasion Pub Crawl

454 Sheridan Rd, Highwood

Celebrate Highwood is hosting both its third annual Elf Invasion Pub Crawl for those 21+ years old, as well as their Elf Invasion 5K Run, Walk, and Stroll. Things kick off at 9:00 am for the 5K and 7:00 pm for the crawl all in downtown Highwood. 

Dec. 4: Santa Hustle Chicago 5K

Santa Hustle 5k photo from 2018

Starting at Soldier Field, this will mark the 2021 Santa Hustle 5k in Chicago. Runners will be clad in red and the iconic Santa hat. The official 2021 charity for the event is Cal’s Angels, which is a pediatric cancer foundation with a mission of granting wishes, raising awareness and funding research to help kids fighting cancer.

Dec. 5: Sing in the Season with the Irish Heritage Singers

1930 Glenview Rd, Glenview

The Glenview Public Library will be hosting an event with the Irish Heritage Singers on Dec. 5 from 3:00 pm to 4:00 pm. According to the event details, “this all-ages choral group embraces the spirit of the season with a sparkling repertoire of traditional and contemporary Irish songs, including a selection of Irish Christmas carols.”

Dec. 7: Women In Leadership Chicago Chef Zoom Panel Discussion

On Dec. 7, a group of talented chefs will share their experiences and lessons they’ve learned in leadership positions. The money from this event will be donated to help women & children who are in refugee camps in Sudan. The charity is HPN4Tigray  (Health Professional Network for Tigray). Sarah Stegner of Prairie Grass Cafe assembled the following chefs to participate: Tigist Reda (Demera) , Lori Seay (Soul Veg City), and Mary Aregoni (Saigon Sisters

Dec. 9: Peanuts Jazz with the Chris White Trio

400 E. Illinois Rd., Lake Forest

The Chris White Trio

The Gorton Center Live Series will be hosting the Chris White Trio at the John & Nancy Hughes Theater. The event is from 7:00 to 8:30 pm. This local group is headed by jazz composer Chris White, who is also an instructor of jazz piano and theory at Lake Forest College, North Park University and North Central College.

Dec. 11-12: Comedian Sebastian Maniscalco

1901 W Madison St, Chicago

Sebastian Maniscalco

The weekend of Dec. 11 will feature comedian Sebastian Maniscalco at United Center at 7:00 pm on Saturday and 5:00 pm on Sunday, bringing his Nobody Does This Tour to Chicago.

Dec. 12: Annual Brunch with Santa

2901 West Lake Ave., Glenview

Come out and have brunch with Santa Claus. The Glen Club right in Glenview will be hosting this event. There will be both buffets for adults and kids to enjoy and soak up the holiday spirit.

Dec. 15: Pentatonix 

6920 Mannheim Rd, Rosemont

The iconic acapela group will be in Rosemont as a part of their Evergreen Christmas Tour on Wednesday, Dec. 15

Dec. 18: Chicago Holiday Market Extravaganza at Northbrook Court Mall

1515 Lake Cook Road, Northbrook

The Northbrook Court Mall is inviting guests for a whole day of holiday shopping. From 10:00 am to 7:00 pm, shoppers can interact with vendors, enjoy music and participate in giveaways.

Dec. 18: Santa’s Drive-Thru Visit

400 Hastings, Lake Forest

Families can head to Dickinson Hall to see Santa and his elves. The event will encourage safety measures in terms of social distancing while also allowing kids to still make their Christmas wishes. 

Dec. 19: Holly Jolly Concert with the Lake Forest Civic Orchestra

Lake Forest Civic Orchestra

The Lake Forest Civic Orchestra is teaming up with Gorton Community Center to share this holiday event. From 3:00 pm to 4:30 pm, families can come experience this musical event right in the Lake Forest community. 

Dec. 19: Skate and Create Gingerbread House Event

305 Randolph St, Glencoe

The Glencoe Park District is hosting a free ice skating event at the Watts Ice Center. Families will be able to enjoy hot chocolate and get a gingerbread house to build together. 

Dec. 23: Trans-Siberian Orchestra comes to Rosemont

6920 Mannheim Rd, Rosemont

 
 
 
 
 
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A post shared by Allstate Arena (@allstatearena)

The Trans-Siberian Orchestra will be putting on a live performance at the Allstate Arena in Rosemont on Dec. 23. From 3:00 pm to 8:00 pm, fans can witness this American rock band perform the best of their holiday music. 

Dec. 30: New Year’s Comedy Laugh Fest

1901 W Madison St, Chicago

On Dec. 30, the United Center will host a plethora of comedians, including Cedric the Entertainer, Eddie Goffin and Nephew Tommy, who are considered some of the best comedians in the industry. 

Dec. 31: Happy Brew Year

4901 Main Street, Skokie

End 2021 with Skokie’s first ever New Year’s celebration, hosted by the Sketchbook Brewing Company. Located in the taproom, guests will be able to enjoy good food and beer as well as live music as they count down the seconds to 2022.


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Sam Stevenson is a journalism and media communication major at North Central College in Naperville, IL. He is an editor in chief for his school’s newspaper and he freelance writes for several sites, including Fansided and 24/7 Sports. He lives in Lisle, IL where he enjoys spending time with his family and dog Sully, playing video games with friends, and writing on his own time!