50 Fun Things to Do in Chicago in December From a Local

There’s no denying the magic of Chicago in December. While the days are shorter and temperatures may drop, the city is bustling with holiday cheer. Chicago glows with Christmas lights as people shop for gifts, attend seasonal events, and soak in the holiday spirit.

I’ve lived in Chicago for nearly two decades, and I’ve written two books about Chicago. I find that December is a great time to visit Chicago if you want to enjoy the festive cheer. Sip on mulled wine at a Christmas market, be dazzled by a holiday performance, or twirl on ice skates with a skyline backdrop. Whether you’re visiting Chicago in December or you live in Chicagoland, here are 50 fun things to do in Chicago in the winter from a local.

If you’re looking for more holiday activities, don’t miss my article on 20 favorite Chicago Christmas traditions!

Some articles on this site contain affiliate links. If you purchase something through one of these links, I may earn a small commission, at no additional cost to you.

Fun Things to Do in Chicago in December

1. Festive Food and Walking Tour

If you want to taste your way through Chicago while taking in the holiday highlights, the Festive Food and Walking Tour is the ticket. You’ll experience holiday traditions like the Christkindlmarket and holiday windows on State Street while sampling deep dish pizza, Italian beef, a Chicago-style hot dog, brownies, and hot apple cider across the three-hour tour.

2. Volunteer to Spread Cheer with Chicago Cares

Lend a hand in the community this holiday season with Chicago Cares. Check out their Holiday Cheer volunteer opportunities to support our neighbors and spread joy.

3. Trace Rudolph’s Roots at Lincoln Park Zoo

Get in the holiday spirit by visiting the deer at Lincoln Park zoo who inspired the creator of Rudolph the Red-Nosed Reindeer! The zoo is always free to visit, so why not? Learn more about Rudolph’s Roots in Chicago.

4. Hear Handel’s Messiah by Music of the Baroque – December 1 and 5, 2025

Who better than Music of the Baroque to perform the heavenly “Messiah” by Handel? Two Grammy-winning artists will be among the performers delivering this homage to hope, faith, and triumph at Symphony Center downtown.

5. Lincoln Park Zoo Holiday Market – December 2, 2025

Lincoln Park Zoo teams up with Nowhere Collective for a festive holiday market. Shop for handcrafted wares like art, home goods, garden gear, fashion, wellness items, and more made by local artisans from reclaimed materials.

6. Elf the Musical – December 2-14, 2025

See Buddy the Elf take the stage at the Auditorium Theater in the Loop for Elf the Musical. Discover the true meaning of Christmas along with Buddy in this hilarious holiday performance. 

Need more information on what to do while you’re in Chicago? Check out all of my Chicago articles and don’t miss my Chicago books Secret Chicago: A Guide to the Weird, Wonderful, and Obscure and Chicago Scavenger!

7. Cheer at the Pier – December 4, 2025

Be part of the grand opening of Winter Wonderfest at Navy Pier with early access to rides, attractions, and ice skating. Enjoy appetizers, a winter cocktail, hot chocolate, and holiday cookies as carolers and a DJ perform. Cheers at the Pier is a fundraiser that supports Navy Pier’s free programming for schools and community groups.

8. One of a Kind Show and Sale – December 4-7, 2025

Shopping for the perfect holiday gifts is as much fun as giving them at the One of a Kind Show and Sale. Hit up the Merchandise Mart in the Loop to browse locally made jewelry, housewares, art, and more. 

9. Happy’s at the Chicago Athletic Association – December 4 – January 16, 2026

The ground floor of the Chicago Athletic Association transforms into a holly jolly dive bar called Happy’s. The nostalgic space transports you to a Midwestern basement bar complete with an animatronic Santa.

10. Go on a Chicago Christmas Tree Crawl

Get into the holiday spirit on this joyful tour of downtown Chicago’s most famous Christmas trees. The 1.5-mile Christmas Tree Crawl will take you to merry locations like the old Marshall Field’s as well as lesser-known locations featuring stunning holiday decor. It’s the perfect way to snap your seasonal selfies! 

11. Winter Wonderfest at Navy Pier – December 5, 2025 – January 4, 2026

If you’re looking for all the magic of the season without having to brave the cold outdoors, find it all under one roof at Winter Wonderfest. Glide on an indoor ice rink, ride Chicago’s Centennial Ferris Wheel, and snap a family photo at holiday displays and attractions. 

12. Millennium Park Holiday Sing-Along – December 5, 12, and 19, 2025

What’s more magical than meeting your neighbors at the Bean to sing holiday carols? A fun Chicago holiday event for families, the free Millennium Park Holiday Sing-Along takes place Fridays between December 5 and December 19 from 6-7 p.m.

13. Cruise the Chicago River in a Hot Tub Boat 

Chicagoans know how to embrace the winter, like partying in a Hot Tub Boat on the Chicago River. The self-captained Hot Tub Boats cruise at one mile per hour for four to six passengers as everyone watches from the shore with envy. It’s one of the most unique Chicago winter activities for friends!

14. The Art Deco Nutcracker – December 6, 2025

The classic holiday performance gets a glitzy twist in the Art Deco Nutcracker. Two performances at the Athenaeum Theatre in Lakeview bring Tchaikovsky’s score to 1920s America in a glamorous rendition.

15. The Music Box Theater’s Christmas Sing-A-Long – December 6-24, 2025

Let your holiday spirit roar while singing along to your favorite Christmas movies. The Music Box’s tradition features screenings of White Christmas and It’s A Wonderful Life complete with a visit from Santa and organ-led carols in the Lakeview theater. 

16. Take A Private Tour Through Chicago’s Festive Lights

If you’re not into the holiday crowds, book this private tour for you and your favorite people. Chicago’s Festive Lights: A Magical Christmas Journey guides you to holiday displays from a downtown skyscraper, down the State Street shopping corridor, and through an outdoor holiday market. It’s a fun way to share the joy of the holidays in Chicago.

17. The Beatrix Potter Holiday Party – December 6 – 28, 2025

If you’re looking for a Chicago holiday event for kids, enjoy a magical performance of the Beatrix Potter Holiday Party. Four favorite characters come to life in this interactive puppet show with original music at the Chicago Children’s Theatre in the West Loop.

18. Mariachi Herencia De México – December 7, 2025

Celebrate Christmas with the sounds of Mexicao at Mariachi Herencia De México.
The Grammy-nominated La Nueva Generación combines classic holiday songs with mariachi traditions for a vibrant Christmas concert at Thalia Hall in Pilsen.

19. Andrew Bird Christmas Concerts – December 8 – 12, 2025

Andrew Bird’s Christmas concerts at the Fourth Presbyterian Church in the Gold Coast. The Grammy-nominated multi-instrumentalist’s Gezelligheid concerts have become a modern Chicago Christmas classic.

20. Enjoy A Charlie Brown Christmas Live – December 9, 2025

The Jody Nardone Trio brings a Christmas classic to live at City Winery Chicago in the West Loop The trio will play music from Vince Guaraldi’s classic album, “A Charlie Brown Christmas,” along with other Christmas favorites. 

21. Adults Night Out at Lincoln Park Zoo – December 11, 2025

Leave the kids at home for Lincoln Park Zoo! Adults Night Out: Holidaze Presented by Grey Goose Vodka and Patrón Tequila. The after-hours holiday party offers glowing holiday lights, free carnival rides, and a DJ spinning holiday tunes. 

22. Kwanzaa Our Way – December 12, 2025

Africa International House hosts an all-day celebration for Kwanzaa Our Way at the Grand Ballroom in Hyde Park. The event is curated for seniors, but attendees of all ages will enjoy lively performances of dance and music.

23. Shop at Sauced Night Market – December 12-13, 2025

The historic Chicago Athletic Association hotel in the Loop is a festive venue for the holiday edition of Sauced Night Market. Pick up unique gifts from local artists and artisans while enjoying bites and cocktails at this free event.

24. Manual Cinema’s Christmas Carol – December 12 – 28, 2025

Enjoy a magical puppet performance retelling this classic holiday story at the Studebaker Theater in the Loop. Manual Cinema’s Christmas Carol brings Dickens’ ghostly tale to present-day Chicago.

25. Go on a Christmas Bar Crawl with TBOX – December 13, 2025

Ah, TBOX, short for the twelve bars of Christmas. It’s a rite of passage for Chicagoans in their twenties to dress in ugly sweaters and bar hop their way through Wrigleyville while carrying boxes of cereal to snack on.

26. Randolph Holiday Market – December 13-14, 2025

Randolph Street Market brings its holiday market to Plumbers Hall in the West Loop. Shop for vintage home wares, clothing, and art as well as holiday décor from more than 125 vendors.

27. Aloft Holiday Market – December 14, 2025

Christmas shopping can be a circus, so why not shop in a circus school? Aloft Circus Arts in Logan Square hosts its Holiday Market from 5-8 p.m. Shop for holiday gifts while sipping a drink and admiring their talented performers. Bring the whole family to this Chicago holiday event as you pose for holiday photos on a trapeze and snap your kids walking a tightwire. Learn more about Aloft in my book Secret Chicago!

28. Enjoy Holiday Caroling at JW Marriott Chicago – Through December 19, 2025

JW Marriott Chicago in the Loop welcomes you to a free live caroling performance in its historic lobby from 3–4 p.m. on December 5, 12, and 19. Drop off your kids’ wish lists at the Letters to Santa Station and check in to themed suites like Winter Wonderland or Classic Christmas.

29. Merry, Merry Chicago! with the Chicago Symphony Orchestra – December 19-23, 2025

What is more moving than hearing a world-renowned orchestra and chorus play your favorite holiday songs in a setting like Orchestra Hall? From “Carol of the Bells” to “Hark! The Herald Angels Sing,” Merry, Merry Chicago! will give these Christmas classics the lavish orchestra treatment.

30. The Chicago Philharmonic Performs The Holiday – December 20, 2025

The modern romcom The Holiday gets the orchestral treatment with music from the Chicago Philharmonic at the Auditorium Theatre in the Loop. Enjoy Hans Zimmer’s score performed live while the film plays in a memorable Chicago holiday event for the whole family.

31. Chanukah Winter Wonderland – December 21, 2025

Celebrate the festival of lights at the Chanukah Winter Wonderland. Newcity in Lincoln Park is transformed into a winter wonderland for the Festival of Lights as folks gather for a free Menorah Lighting at 5:30, kosher treats, hot chocolate, kids’ activities, and a live DJ.

32. Santa’s North Pole Brunch at the Four Seasons – December 21, 2025

Join Santa for a decadent meal at the Four Seasons that is also a magical Chicago Christmas event for kids. The Gold Coast hotel will feature seasonal face painting and balloon art along with a visit from Santa Claus himself at Santa’s North Pole Brunch.

33. Ice Skate at the Peninsula Sky Rink

Chicago’s chicest ice skating experience is found in the Gold Coast on the terrace of The Peninsula Chicago—one of the city’s most exclusive hotels. Show off your moves on the 2,100-square-foot Sky Rink offers while overlooking Michigan Avenue before warming up with a hot drink in the chalet.

34. Try Curling at the Gwen

Try a new activity on the luxurious Gwen Hotel’s cozy rooftop terrace. Winter Curl & Chill invites you to check out the curling lanes with your crew before curling up at a fire pit with a hot cocktail.

35. Be Dazzled by Winter Fireworks – Through December 27, 2025

Fireworks at Navy Pier are synonymous with summer in Chicago. Yet Navy Pier’s Winter Fireworks bring the free, breathtaking display back every Saturday at 8 p.m.

36. It’s A Wonderful Life at the American Blues Theater

The story of a man looking for a miracle has resonated with audiences from film to state. See why It’s A Wonderful Life has been a tradition at American Blues Theater in West Ridge for almost 25 years.

37. Book Swissôtel Chicago’s Santa Suite – Through December 28, 2025

Swissôtel Chicago offers enviable views of the Chicago River and skyline all year, but its Presidential Suite transforms into the Santa Suite for the holiday season. The 2,000-square-foot suite’s halls are decked with enough holiday cheer to make Santa himself jealous.

38. Who’s Holiday! At Theater Wit – Through December 28, 2025

An adult Cindy Lou Who spills the tea from her trailer home for Who’s Holiday. Learn her sordid story, complete with vodka, weed and profanity at Theater Wit in Lakeview. 

39. Chateau Carbide’s Winter Garden

Cozy up on the rooftop of the Pendry Hotel in a chalet with fake furs and a tableside fireplace. The Winter Garden offers a whimsical holiday setting for groups with a menu of seasonal drinks.

40. Visit a Christmas Pop-up Bar

Christmas bars abound all across Chicago. Frosty’s in Lincoln Park claims to be the first—think life-size Nutcrackers and a cocktail inspired by the Grinch. In Wrigleyville, Big Star’s Holiday Honky Tonk puts a Tex-Mex spin on the holiday season with a Rhinestone Rita and Winter Old Fashioned. Around the corner, Santa Baby offers a big space for groups complete with Jingle Juice and Grinch milkshakes. Also in Wrigleyville, Elf’d Up has 1,000 elf figurines on display and a menu with Buddy’s breakfast pasta of spaghetti topped with maple syrup, chocolate fudge, and mini marshmallows.

41. Gatsby’s Prohibition New Year’s Eve Gala – December 31, 2035

If you want to get dolled up and party like it’s the Roaring Twenties, buy a ticket for Gatsby’s Prohibition New Year’s Eve Gala. Dress in your Prohibition-era best and head to Morgan Manufacturing in the West Loop for drinks, desserts, and a midnight celebration.

42. New Year’s Eve Fireworks at Navy Pier – December 31

What better way to welcome 2026 than with a free Chicago New Year’s Eve event? Enjoy a magical fireworks display at Navy Pier synchronized to music as you celebrate with friends and family.

43. Dick Clark’s New Year’s Rockin’ Eve – December 31, 2025

Be part of the very first Chicago’s broadcast on ABC’s Dick Clark’s New Year’s Rockin’ Eve.  The free public event features live performances by artists like Chance the Rapper and Shemekia Copeland, a midnight countdown, and a dazzling fireworks display on the Chicago River.

44. 8 Crazy Nights – Through January 2, 2026

Celebrate the Festival of Lights at Chicago’s first and only Hanukkah-themed pop-up bar. Head to the Greystone Tavern in Lakeview for 8 Crazy Nights complete with a blue-and-white light display, a lighted menorah,  and a Hanukkah sweater wall.

45. Winter Flower Show at Garfield Park Conservatory – Through January 4, 2026

Lush plants and colorful plants greet you at Garfield Park Conservatory’s “Merry & Bright” show. Admire poinsettias with cheery names like ‘Viking Cinnamon’ and ‘Candy Wintergreen’ and see Christmas lights glow on the Frasier Fir trees.

46. BYOB Holiday Lights Trolley

Enjoy Chicago’s holiday lights from the comfort of a vintage trolley for the BYOB Holiday Lights Trolley. Bring your own beverages and hop between Chicago’s holiday landmarks from Matilda to the Christkindlmarket, Magnificent Mile, Millennium Park’s Christmas Tree, and Lincoln Park ZooLights.

47. The Real Housewives of the North Pole  – Through January 3, 2026

Hell in a Handbag Productions presents the Real Housewives of the North Pole at the Clutch in Lincoln Square. When the North Pole is in trouble, the holiday divas try to claw their way to fame with reality TV.

48. Jack Frost Pop-Up Market

Deck the halls at Jack Frost in in Fulton Market for Chicago’s biggest outdoor Christmas pop-up market. The family-friendly Chicago Christmas event offers ice skating, curling, Christmas chalets, axe throwing, and more.

49. Winter Wonderland at the Godfrey Hotel

Discover a magical world waiting for you on the rooftop at the Godfrey Hotel in River North. Winter Wonderland offers cozy igloos for up to eight friends to share cocktails while admiring Chicago’s skyline views.

50. Holiday Fashion Tea at the Waldorf Astoria – Through January 12, 2026

Admire the latest couture from local designers while sipping and snacking at the Waldorf Astoria in downtown Chicago. Holiday Fashion Tea at Brass Tack delivers premium tea and champagne in a chic fireplace setting while you get inspired by the latest in design.

Visiting Chicago in December FAQ

Is December a Good Time to Visit Chicago?

December is a delightful time to visit Chicago. There is always the chance of a snowy wonderland in December, but the magic of the holiday season is guaranteed. There is no shortage of holiday events, performances, and pop-ups to maximize your festive feelings. Many people visit Chicago to enjoy its Christmas traditions in December, but you can still find cheaper flights and hotel deals than you can during other busy times. I recommend booking ahead, especially around the Christmas holiday, for popular restaurant reservations and tickets to Chicago’s top attractions like the Field Museum, 360 Chicago Observation Deck, or the Art Institute, to skip the lines.

What is Chicago Weather like in December?

December in Chicago can deliver sunny winter weather or blizzard conditions. According to the National Weather Service, the average temperatures in Chicago in December range from a high of 36 degrees to a low of 24 degrees. With shorter days and less sunshine, you should maximize your daylight hours. Snow is always a possibility, and chilly winds are always present. The weather can shift rapidly, so be sure to check the forecast before you visit Chicago in the fall so you can pack accordingly.

What Should I Wear to Chicago in December?

If you’re wondering what clothes to wear to Chicago in December, I recommend packing layers. The weather will be chilly and maybe even snowy, and you may experience a cold breeze off Lake Michigan. Check the weather before you visit Chicago in December so you can pack appropriately.

After nearly two decades of living in Chicago, here are my recommendations for what to wear in Chicago in the winter.

• Chicago is a walking town, so pack comfortable shoes like sneakers or boots. A lug boot will keep women’s feet warm. If it’s snowing, consider a duck boot for men and for women.
• Wool socks for men and women.
• Thermals to wear under your jeans for men and women.
• Dress in layers so you can adjust to the different temperatures indoors and outdoors. Merino wool makes a great base layer for men and women. You may want to layer with a women’s flannel or a men’s flannel.
• A classic button-down Oxford or chambray shirt is great for traveling, and I’ve never met a striped Breton shirt that I didn’t like.
• If the forecast calls for winter weather, pack a long jacket, preferably one made with down.
• It doesn’t hurt to pack a windproof travel umbrella for rainy days.
• Bring a beanie and my favorite merino wool gloves for winter weather. Don’t forget a scarf!

Where to Stay in Chicago in December

Wondering where to stay overnight in Chicago for the holidays? I love the views of Grant Park from the Blackstone Hotel and the iconic pool at the InterContinental. The Chicago Athletic Association has a rooftop fire pit and great views of Millennium Park’s Christmas tree, while the LondonHouse boasts beautiful views of the Chicago River from its rooftop bar.

Click here for a full list of Chicago hotels!

If you want to research hotels and vacation rentals for your Chicago visit, this map can help you compare the available options. It’s set to show hotels and rentals in downtown Chicago, but you can view any neighborhood where you’d like to stay.

I hope this helps you get excited to visit Chicago in December!

Find out what to do in Chicago throughout the year:

• Fun Things to Do in Chicago in January
• Fun Things to Do in Chicago in February
• What to Do in Chicago in March
• Fun Things to Do in Chicago in April
• Fun Things to Do in Chicago in May
• What to Do in Chicago in June
• Fun Things to Do in Chicago in July
• What to Do in Chicago in August
• Fun Things to Do in Chicago in September
• What to Do in Chicago in October
• Fun Things to Do in Chicago in November

Like this story? Pin it for later.