December 2025 in Chicago: Holiday Lights, Cultural Celebrations & Festive Neighborhood Events

December is one of the most vibrant months to live in or explore Chicago. Across every neighborhood — from Lincoln Park and Lakeview to West Loop, Andersonville, and the Loop — the city comes alive with holiday traditions, multicultural celebrations, concerts, markets, and family-friendly events.

Here’s your curated guide to the best things to do in December 2025, including Christmas classics, Hanukkah celebrations, pop-ups, and places to ring in the New Year.

This year marks the 34th year of the Chicago CTA Holiday Train! The schedule was released, and today starts service to the north side! Use the CTA Tracker to know when it’s near you!

🟢 Green Line: Nov 28 & 29, Dec 2
🟠 Orange Line: Nov 28, Dec 2-6
🟤 Brown Line: Dec 3-6
🔵 Blue Line: Dec 11-13
🔴 Red Line: Dec 16, 18 & 20
🟣 Purple Line: Dec 17, 19 & 20
🟡 Yellow Line: Dec 22
💗 Pink Line: Dec 9, 10 & 13

Holiday Music, Concerts & Sing-Alongs

Caroling at the Bean
December 5, 12, 19 • 6–7 PM
Chicago’s most joyful December tradition returns with local choirs leading a community sing-along in front of Cloud Gate.

Music Box Christmas Sing-A-Long
December 6–24
A Chicago classic featuring an organ-led sing-along, Santa appearance, and screenings of It’s a Wonderful Life and White Christmas.

Holiday Lights, Family Favorites & Seasonal Traditions

ZooLights at Lincoln Park Zoo
November 21 – January 4
4:30–9 PM (Sunday–Thursday) · 4:30–10 PM (Friday–Saturday)
One of Chicago’s most beloved holiday traditions with millions of lights, displays, rides, and seasonal treats.

Winterland at Gallagher Way + Christkindlmarket Wrigleyville
November 23 – December 31
Winter rides, ice skating, Santa’s Workshop, and a full European-style holiday market with mulled wine, ornaments, and seasonal food.

Santa Hustle Chicago 5K
December 6 · Montrose Harbor
Costumes, cookies, hot cocoa, and an upbeat seasonal run.

Photos with Santa

Gallagher Way
Weekends in December

Wonder City at New City
December 21, 10 – 6

Santa at the Driehaus Museum
December 6 and 13, 9 – Noon

Ice Skating

Millennium Park Rink

Maggie Daley Ribbon

Shop Small: Holiday Markets & Neighborhood Events

Southport Holiday Cocktail Crawl: December 5th, 5 – 9 PM *tickets required
Boutiques stay open late with festive treats, live music, and neighborhood cheer.

Late Night Andersonville: December 12th, hours vary
One of the best nights of the season for supporting local makers, boutiques, and cafés.

Christkindlmarket Wrigleyville: Open daily through December
Mulled wine, handmade ornaments, artisanal treats, and an energetic neighborhood atmosphere.

Jack Frost Holiday Pop-Up — Fulton Market
A festive mix of ice skating, rides, light mazes, bumper cars, and Santa visits.

Hanukkah: Celebrations & Community Events

Chicago’s Hanukkah celebrations welcome all ages and backgrounds.
Community Menorah Lightings
Andersonville
December 14, 4 – 5 PM

Lakeview
December 14, 6 – 7:30 PM

Daley Plaza
December 16, 5:30 PM

West Loop
December 23, 4 PM

Holiday Sparkling Events

Le Sud Holiday French Bistro Classics
December 9, 6:30 PM

Le Sud Champagne & Sparkling Wines Tasting
December 11, 6:30 – 9:30 PM

Eataly Sparkles & Sweets
December 18, 5:30 – 6:30 PM

Ella Elli 20 for $20 Glitter & Bubbly Holiday Sparkling Spectacular
Multiple dates & times. Tickets on Tock

Binny’s Veuve Clicquot PopUp Bar and much more!
December 20, Noon – 3 PM

Chicago will be center stage for
Dick Clark’s New Year’s Rockin’ Eve for the first time ever!

NYE: Where to Ring in 2026

LondonHouse Rooftop Igloos or the Ballroom

Four Seasons

Navy Pier Aon Gala

Chicago River Fireworks

New Year’s Day Brunch in Chicago

🧇 Adorn, Four Seasons

☕ Beatrix

🥞 Summer House Pajama Brunch

🍳 Café Ba-Ba-Reeba

🍣 Miru (St. Regis)

December in Chicago offers something truly special — from cultural celebrations and holiday lights to family outings, shopping local, and ringing in a fresh new year. Whether you’re exploring the city with visitors, planning a festive date night, or enjoying the season close to home, there’s so much to experience in our neighborhoods.

✨ For more monthly guides, neighborhood events, and Chicago real estate insights, follow along at Chicago Dream Home.

🖤 Thanks for following along each month as we share Chicago’s best local experiences. If you’d like neighborhood updates, market insights, and curated event guides straight to your inbox, subscribe to Dream Home Press—it’s your local’s pass to all things Chicago.