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.
Don’t forget to tag us in your posts on Instagram @betterchicago!
All Month Long
Lost in Lake Forest Suite Experience at the Deer Path Inn
255 East Illinois Rd., Lake Forest
“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
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
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
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
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 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
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
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
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 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
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
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
View this post on Instagram
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.
More from Better:
- Where to See Holiday Lights Around Christmas This Season
- 2021 Holiday Gift Guide: The Best Gifts for Everyone on Your List
- 2021 Gift Guide: The Best Jewelry Gifts to Dazzle Your Loved Ones
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!
