31 of The Best Things To Do in Chicago and the North Shore This December

The holiday season asks a lot of us. From shopping, to holiday events, to get-togethers — how do we squeeze the most out of this festive time before it passes us by? To help solve this seasonal problem, Better has conjured up a list of the best 31 things to do in Chicago this December — from caroling to the symphony, from Hanukkah events to holiday markets. Whether you’re looking for family fun or grown-up holiday merriment, we’ve got you covered.

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The Nutcracker

Joffrey Ballet, The Nutcracker | Choreographer: Christopher Wheeldon, Music: Peter Ilyich Tchaikovsky | Photo courtesy: © Todd Rosenberg Photography 2021


The ballet that has captivated seasonal and devotee audiences for decades, The Nutcracker, comes to The Joffrey Ballet this month, Dec. 3-27. This two-hour, iconic performance will be held at the Lyric Opera House and has been described as “pure winter magic.” Interested parties can visit The Joffrey Ballet website to purchase tickets and learn more about the performances.

20 N. Upper Wacker Dr.

Macy’s Holiday Celebrations


If you love the holidays in Chicago, chances are you’ve been waiting all year for the Macy’s Holiday Window Display in all its good cheer — running until New Year’s Day. The classic State Street store also welcomes parents and kids alike to pop up to the 5th floor for Macy’s 2022 Santaland, where kids can visit and take a photo with Santa. Reservations are required and should be made at least five days in advance, but not to worry, Santa and his elves will be around until Dec. 24 — leaving plenty of time to still book. Visit the Macy’s Holiday Celebration website for registration and more information.

111 N. State St.

Ornaments For All

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Buddy is a store within the Chicago Cultural Center dedicated to showcasing the work of over 200 local artists and small manufacturers. With exhibitions, workshops, launches and so much more, Buddy seeks to spread roots of creativity across the city, for both visitors and locals alike. This holiday season, they will host their second annual “Ornaments for All” — an ornament show featuring one-of-a-kind work from 30-plus Chicago artists. The exhibit ends Dec. 31 with an opening reception on Dec. 6. Additional information can be found on the Chicago Cultural Center website.

78 E. Washington St.

Hershel and the Hanukkah Goblins

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Based on the book “Hershel and the Hanukkah Goblins,” this production follows a traveling troupe of actors who find a town void of people celebrating Hanukkah. Can they bring back the spirit of of the holiday? Find out in Strawdog Theatre Company’s rendition, held at The Edge Theater in Edgewater, Dec. 11 through Jan. 1. Tickets, both for in-person and virtual streaming, can be reserved on the Strawdog Theatre website.

5154 N. Broadway

FORTS! Build Your Own Adventure


Looking for a unique experience for your kids? Or ready to revive your inner child? Look no further than FORTS! Build Your Own Adventure — a play space where visitors can build new worlds using objects like cardboard boxes, bed sheets and more; perfect for children with a penchant for creation. Adults can get in on the fun, too, with FORTS! Adult Night, a BYOB evening of play. FORTS! Build Your Own Adventure — put on by Filament Theatre — is open now through Jan. 8, and FORTS: Adult Night until January 6. Specific dates and more information can be found on the FORTS! Website.

4041 N. Milwaukee Ave.

Shark Feeding Tour

Photo courtesy of Shedd Aquarium


Be transported 8,000 miles away to the Indo-Pacific reef as the Shedd Aquarium gives guests from ages six and up an in-depth look at sharks and their lifestyle. This 75-minute behind-the-scenes experience allows visitors to witness meal time, learn how to prepare a meal fit for a shark, all while picking up facts from Shedd experts. Don’t miss this opportunity — available weekends only, now through the end of December. Event specifics can be found on the Shedd Aquarium website.

A Christmas Carol

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Charles Dickens’ classic holiday tale, “A Christmas Carol,” is alive on the stage again this winter at the Goodman Theatre. The show will run at the Loop-based theater all throughout the month of December. Audiences can grab their tickets now by visiting the Goodman Theatre website.

170 N. Dearborn St.

December 1-4:  One of a Kind Show + Sale 


Returning for its 21st year, the One of a Kind Show + Sale is bringing together 500 artists and makers of different mediums for one big holiday sale. Hosted at The Mart, thousands of annual shoppers secure “unique and meaningful” gifts that range from niche to must-haves. From accessories to home goods; pet products to bath and beauty, this showcase has it all. Check out more details on the One of a Kind website.

222 W. Merchandise Mart Plaza

December 2: Southport Holiday Stroll & Cocktail Crawl


From 5-9pm, crawl along Southport for an evening of cocktails, carolers, photos with Santa and much more. Strollers can also take advantage of special deals at participating local businesses from cafes to corner stores. View the full list of businesses and what other holiday surprises await you at the Lakeview Roscoe Village website.

Down Southport, from Belmont to Irving Park

December 2-3: Pre-Kwanzaa Marketplace


This Kwanzaa-inspired marketplace will host many vendors for attendees to peruse and shop from, but that is only the beginning. The Pre-Kwanzaa Marketplace also has a weekend full of programming from poetry to workshops to music and more — with acts including Maggie Brown and Al Smith. Visit the African International House website for a complete line up of acts and opportunities at the marketplace.

December 2-3: RomaDrama Christmas


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Hallmark Christmas movie lovers gather ‘round! Some of your on-screen favorites are coming to the Windy City for a weekend of meet-and-greets, screenings and photo-ops. Join them for a swanky cocktail party; grab “grown up brunch” with Santa and his elves; or catch exclusive movie previews — all available at varying price packages. Want to be immersed in the world of holiday rom-coms? Visit the RomaDrama Christmas website for more information.

December 2-4: Andersonville Winter Market


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Back for its second year, the Andersonville Winter Market, hosted by the Andersonville Chamber of Commerce, will be in full swing offering shoppers a variety of treasures from handcrafted goods to vintage finds. While perusing 20+ vendors, enjoy daily live entertainment and a warm cup of Glögg courtesy of Simon’s Tavern. Daily hours vary, visit the ACC website for more information and a full lineup of participating businesses.

Catalpa and Clark

December 3: Santa Hustle 5K


Head over to Soldier Field this weekend for a 5K race devoted to ole’ St. Nick. This fan-favorite race — and Kids Dash — brings together the fun of a Chicago-based 5K and the hilarity of dressing up like Mr. Clause himself. Deck out head to toe in the iconic, Santa-red clothes and kick-off this holiday season on the right foot. More information and registration can be found on the Santa Hustle website.

December 3: Too Hot to Handel: The Jazz-Gospel Messiah


For 17 years, the “exuberant, jazz-gospel makeover” of Händel’s classic Messiah — “Too Hot to Handel: The Jazz-Gospel Messiah” — has brought jazz lovers to Auditorium Theatre. The awe-inspiring performance features world-class musicians comprising a chamber orchestra, jazz combo, choir in addition to three soloists. Dubbed “not your grandmother’s” choir performance, it is an experience worth turning out for. Visit the Auditorium Theatre website for more details.

50 E. Ida B. Wells Dr.

December 3-4: Wreath Making Workshops


Want to add a touch of seasonal decor to your home? Than you might be interested in attending the Wreath Making Workshop at Gallagher Way’s Winterland, hosted by Indigo & Violet Studio. The workshop lets guests “make a fragrant, one-of-a-kind holiday decoration,” whether they follow an instructor-led design or make something unique. Tickets are $55, visit the Indigo & Violet Studio website for class specifics.

3635 N. Clark St.

December 3-4: A Christmas Carol at The Community House Winnetka


Another rendition of this Christmas classic is showing for a limited time this month, held at and in support of Community House Winnetka — a center that provides public programming for everyone in the larger-Winnetka community. To reserve tickets or for more information, visit the Community House webpage

620 Lincoln Ave., Winnetka

December 4: Annual Crèche Exhibit at Loyola University Museum of Art

“Chicago Nativity” by R. Michael Palan commissioned for The James and Emilia Govan Crèche Collection, on display in LUMA | Photo by Lukas Keapproth


This annual tradition, hosted by the Loyola University Museum of Art, returns for another triumphant year, boasting an impressive lineup of 60 different nativity-inspired crèches from over 50 countries. Visitors to this free attraction are encouraged to bring a new hat, socks or mittens to be donated to Loyola Labre and other homeless ministries. If you can’t witness the exhibit now, you can still catch it Dec. 9-11. Additional information located on the LUMA webpage.

December 4: Holiday Sale at The Book Stall


Known across the North Shore for its wide selection of literature and knick knacks as well as a space for community programs, The Book Stall is having a Holiday Sale! Shoppers can enjoy 20% off select items such as cards, puzzles, journals and other gift items. If you want to shop and support local this holiday season, this is a great place to start. Sale specifics can be found on The Book Stall website.

811 Elm Street, Winnetka

December 5: Walt Disney’s Birthday Celebration


The Walt Disney Birthplace will host a celebration of Walt Disney’s birthday at Walt’s birthplace home in Chicago’s Hermosa neighborhood, in partnership with the YMCA of Greater Metropolitan Chicago.

Dorri McWhorter, President and CEO of YMCA of Metropolitan Chicago, said, “We are thrilled that the YMCA is joining the celebration at The Walt Disney Birthplace this year to honor the birth of Walt and his continuing legacy of fostering creativity and innovation.”

This year’s Miss Illinois USA, Angel Reyes, who was born and raised in Hermosa, will also be in attendance at the event, which will include a candle-lighting ceremony, holiday songs by Nixon Elementary students, and holiday treats for all who attend. The free event begins at 5:30pm.

2156 N. Tripp Ave. Chicago, IL 60639

December 5-6: Michelle Obama at the Chicago Theatre


Former First Lady Michelle Obama returns to her hometown for a two-day stopover as a part of her new book tour, “The Light We Carry.” The discussion, held at The Chicago Theatre, will be moderated by David Letterman on the 5th and Heather McGhee on the 6th. Interested parties can find tickets and more on The Light We Carry webpage.

175 N. State St.

December 6-11: A Magical Cirque Christmas


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These daring and dazzling acts will thrill audiences of all ages at this live event. What’s more, performers and cirque artists will be joined by live holiday music thanks to Broadway In Chicago. Held at the CIBC Theatre in the Loop’s Theatre District, it makes for a great family night out or even a date night. Visit the Magical Cirque website for tickets and event specifics.

December 10: The Holly Jolly Holiday Market


We can’t forget that the holidays are also a time for connection with people in our community. To that end, The North Center Neighbors Association is hosting the Holly Jolly Holiday Market which will be a time for not only shopping local vendors or enjoying music, but eating and drinking with neighbors as you get to know them. Visit the NCNA website for specifics about the market and its lineup.

4100 N. Damen Ave.

December 10: Heart of the Holidays


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The final installment of the City of Highland Park’s four-weekend holiday series, Heart of the Holidays, brings Santa and Mrs. Claus for kids and parents to enjoy; gingerbread house making courtesy of Renaissance Place; holiday carolers; a Klezmer band; dreidel making; a Toys for Tots drive and more. Head over to the City of Highland Park website for more.

December 10: Center Days at the Hyde Park Art Center



One of the many jewels of Chicago is its art scene, from North to South, East to West, the city is crawling with creation. Including at the Hyde Park Art Center, where this December they are offering Center Days — a day of free admission to the center that includes “immersive art exhibitions” and activities. These days only come around quarterly, don’t miss your chance to see all of the museum’s contemporary wonder! Visit the Hyde Park Art Center website for more details.

December 11: 10th National Vigil to #EndGunViolenceChicago


Gun violence continues to plague our nation — even in 2021, Chicago saw more than 800 homicides. To combat this, survivors, families of victims and concerned citizens are banding together for the 10th Annual National Vigil to #EndGunViolenceChicago. The vigil will be held at Augustana Lutheran Church of Hyde Park starting at 6pm. Come with nothing but an open heart to support the community with. More information available thanks to Chicago Survivors — a crisis and support organization for those facing violence or grief.

5500 S. Woodlawn Ave.

December 11: Holiday Cheer Challenge


The Honeycomb Project will host its second annual Holiday Cheer Challenge in Millennium Park this year, where more than 200 Chicagoans of all ages will participate in a scavenger hunt. The hunt infuses “giving back” with adventure and will send participants on a race downtown, performing acts of cheer all while raising funds for Honeycomb’s mission. To get involved, visit The Honeycomb Project website.

December 13: St. Lucia Festival of Lights

Photo courtesy of Andersonville Chamber of Commerce


St. Lucia Day is celebrated annually in December, and this year the Swedish American Museum will host their annual crowning ceremony for all to enjoy. The “traditional candle-lit procession” will begin in Andersonville at the Swedish Museum and work its way down Clark St. — though the procession may vary depending on which performance you attend. The streets will be filled with children singing “The Lucia Song,” donned in long white robes as well. Whether you share in this rich history or not, this event is unlike any other and will melt the hearts of anyone who appreciates the beauty of the holidays. Visit the Andersonville Chamber of Commerce page for more details.

Starts at Nordic House, 400 N. Michigan Ave.

December 14: Hoppy Holidays Movie Trivia


The Cinema/Chicago Associate Board welcomes cinephiles to their Hoppy Holidays Movie Trivia night. Hosted at Midwest Coast Brewing Co., the evening will test your holiday movie knowledge, while also enjoying some tasty brews and potentially winning some prizes — not to mention all the yuletide cheer! This event starts at 6:30pm and can even be enjoyed from home with their virtual option. See the Cinema/Chicago website for all the details.

2137 W. Walnut St.

December 16: A Night at the Museum


Chicago-native, Grammy-winner Chance The Rapper’s organization, SocialWorks, has done so much in regards to connecting with Chicago youth and community outreach. And that continues this year, as they bring back their 4th annual Night at the Museum event — the first one since the onset of COVID. Youth and their families will join SocialWorks for an after-hours tour of the Museum of Science and Industry, including 50+ event-only vendors, activities, performers, “unique Chance opportunities,” and the entire museum! But this night is about more than just fun, it is also a chance for participants to donate warming items like coats, scarves, gloves, toys and hygiene items — which will all be donated to our neighbors experiencing homelessness. See how you can get involved with this event or their mission by visiting the SocialWorks website.

December 16-23: Merry, Merry Chicago!

christmas symphony Photo courtesy of Chicago Symphony Orchestra
Photo courtesy of Chicago Symphony Orchestra


Music is an integral part of holiday celebrations — from carols to classic tunes, they are synonymous with this time of year. There are few better ways to experience this music than live with the Chicago Symphony Orchestra, who will host their show “Merry, Merry Chicago!” from Dec. 16-23. Perfect for a night out on the town or for the whole family to enjoy. You can reserve tickets now by heading over to the Chicago Symphony Orchestra website.

December 18-25: 8 Nights of Hanukkah with JCC Chicago

8 Nights of Hanukkah from years past | Photo courtesy of JCC Chicago


As Hanukkah approaches, JCC Chicago invites folks — both in-person and virtually — to join them as they celebrate each of the eight nights of Hanukkah with a different activities. Night to night, enjoy dreidel competitions, live entertainment, an ice cream social, singalongs and more. No better way to bring in this holiday than in the presence of others — visit the Jewish Community Center Chicago for more details about nightly events.

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Margaret Smith is a Chicago-based writer and editor with a passion for socio-political storytelling about their community. They are a graduate of Columbia College Chicago.

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