Chicago transforms into a winter wonderland in December. Holiday lights, festive markets, and cozy experiences await first-time visitors.
Don’t let the cold weather keep you inside all day. The city’s best attractions shine brightest during the holiday season.
This Chicago December itinerary covers everything you need for your trip. From free activities to can’t-miss experiences, we’ve got you covered.
Christkindlmarket: Chicago’s Beloved German Holiday Market
No December visit is complete without Christkindlmarket. This German-style Christmas market is a Chicago holiday tradition.
Three locations operate during the 2025 season. All markets offer free admission with paid food and gifts.
Christkindlmarket Chicago at Daley Plaza
Address: 50 W. Washington St., Chicago
Dates: November 21 through December 24
Hours: Sunday through Thursday, 11 AM to 8 PM. Friday and Saturday, 11 AM to 9 PM.
This is the original and largest Christkindlmarket location. Expect wooden huts, roasted nuts, and hot spiced wine.
The famous boot-shaped souvenir mugs return this year. Glühwein tastes better when sipped from a collectible mug.
https://www.christkindlmarket.com/
Christkindlmarket Wrigleyville at Gallagher Way
Address: 3635 N. Clark St., Chicago
Dates: November 23 through December 31
Hours: Monday through Thursday, 3 PM to 9 PM. Friday and Saturday, 11 AM to 10 PM. Sunday, 11 AM to 7 PM.
This location offers a more relaxed experience overall. It runs through New Year’s Eve for extended enjoyment.
Any Chicago December itinerary should include at least one Christkindlmarket visit. The Wrigleyville location pairs perfectly with neighborhood exploration.
Christkindlmarket Aurora at RiverEdge Park
Address: 360 N. Broadway, Aurora, IL
Dates: November 21 through December 24
Hours: Thursday, 11 AM to 7 PM. Friday and Saturday, 11 AM to 9 PM. Sunday, 11 AM to 6 PM.
The Aurora market features over 60 vendors this year. It’s perfect for families avoiding downtown crowds.
Budget tip: Bring your own mug from previous years for refills. Plan to spend $40 to $50 per person for food and small gifts.
Millennium Park: Chicago’s Winter Centerpiece
Millennium Park becomes magical during the holiday season. The 112th Annual Chicago Christmas Tree anchors the celebration.
Chicago Christmas Tree
The 68-foot Norway spruce stands near Michigan Avenue and Washington Street. It’s decorated with 39,250 feet of glimmering lights.
The tree remains illuminated through January 11, 2026. Visit after dark for the most spectacular photo opportunities.
https://www.chicago.gov/city/en/depts/dca/supp_info/tree0.html
McCormick Tribune Ice Rink
Dates: November 21, 2025, through February 1, 2026
Sessions: 11 AM, 1 PM, 3 PM, 5 PM, 7 PM, and 9 PM
Admission: Free with reservation; skate rentals start at $17
This is Chicago’s version of Rockefeller Center skating. The Bean and Christmas tree provide a stunning backdrop.
Free skating lessons are available on weekend mornings. Register online for Saturday and Sunday 9 AM sessions.
Reservations are required for all skating sessions. Book online at least two weeks in advance.
Ice skating at Millennium Park belongs on every Chicago December itinerary. It’s the city’s most iconic winter experience.
https://www.chicago.gov/city/en/depts/dca/supp_info/millennium_park10.html
Millennium Park Holiday Sing-Along
Dates: Fridays, December 5, 12, and 19 at 6 PM
Location: Grainger Plaza near Cloud Gate
This free event features live performances of holiday classics. Gather under the glow of The Bean for caroling.
https://www.chicago.gov/city/en/depts/dca/supp_info/tree0.html
ZooLights at Lincoln Park Zoo
Dates: November 21, 2025, through January 4, 2026
Hours: 4:30 to 9 PM Sunday through Thursday. 4:30 to 10 PM Friday and Saturday.
Address: 2001 N. Clark St., Chicago
This beloved tradition features over 3 million LED lights. Festive displays illuminate the zoo’s walkways and exhibits.
Tickets cost $7 to $12 depending on the date. Free admission is available on select Mondays with reservations.
The Ferris wheel offers stunning views of the lights below. Carousel rides and the Light Maze cost extra.
Santa visits through December 23 for photos. S’mores, hot chocolate, and churros are available for purchase.
Sensory-Friendly Night: November 25 features static lights and quieter music. This is ideal for visitors sensitive to stimulation.
https://www.lpzoo.org/event/zoolights/
Winter WonderFest at Navy Pier
Dates: December 5, 2025, through January 4, 2026
Location: Festival Hall, Navy Pier
This indoor holiday experience stays warm and dry. Rides, slides, and ice skating await inside Festival Hall.
Every ticket includes a ride on the Centennial Wheel. Views from 200 feet showcase the pier’s holiday lights.
Attractions include bumper cars, the Zero Gravity ride, and inflatables. The Verizon/Google Pixel Ice Rink offers skating indoors.
Santa visits on select dates through December 23. Professional photos are available for purchase.
Bonus: Winter WonderFest tickets include free child admission to Chicago Children’s Museum.
Winter WonderFest is essential to any family Chicago December itinerary. Kids stay entertained for hours inside the heated venue.
https://navypier.org/winterwonderfest/
CTA Holiday Train and Bus
Dates: Train runs November 29 through December 22. Bus runs November 28 through December 21.
Cost: Free (regular CTA fare for riders)
The CTA Holiday Train is a Chicago tradition. Six vintage train cars are decorated with twinkling lights.
Santa and his reindeer wave from outside the train. Spot the festive locomotive at CTA stations throughout the city.
The Holiday Bus cruises city streets spreading cheer. You might randomly encounter it on your travels.
Check CTA’s website for route schedules and timing. The train makes appearances across multiple lines daily.
https://www.transitchicago.com/
Holiday Theater and Performances
Chicago’s theater scene delivers spectacular holiday shows. Book tickets early as performances sell out quickly.
The Nutcracker by Joffrey Ballet
Dates: December 5 through 28, 2025
Location: Lyric Opera House, 20 N. Wacker Dr.
This production is set at Chicago’s 1893 World’s Fair. Tony Award-winning choreographer Christopher Wheeldon created this version.
The Joffrey’s Nutcracker is Chicago’s top holiday tradition. Tchaikovsky’s score accompanies breathtaking choreography and costumes.
Adding a show elevates any Chicago December itinerary from good to unforgettable. The Nutcracker sells out fast, so book early.
A Christmas Carol at Goodman Theatre
Dates: November 15 through December 31, 2025
Location: Goodman Theatre, 170 N. Dearborn St.
This cherished Chicago tradition brings Dickens to life annually. Stunning performances and enchanting sets capture the holiday spirit.
The production is perfect for all ages. It’s been running at Goodman for nearly 25 years.
https://www.goodmantheatre.org/
It’s a Wonderful Life at American Blues Theater
Dates: November 21 through December 28, 2025
This unique production unfolds as a 1940s radio broadcast. George Bailey’s timeless story resonates with audiences every year.
Merry, Merry Chicago! at Symphony Center
Dates: December 19 through 23, 2025
Location: Symphony Center, 220 S. Michigan Ave.
The Chicago Symphony Orchestra performs holiday classics annually. Expect beloved carols and high-energy medleys throughout.
World-Class Museums (Many with Free Days)
Chicago’s museums offer perfect escapes from December weather. Many offer free admission for Illinois residents this month.
Art Institute of Chicago
Address: 111 S. Michigan Ave.
Free Days: Weekdays, December 1 through 18 (Illinois residents)
The Art Institute houses an extraordinary collection of masterpieces. Impressionist and post-impressionist works are particularly stunning.
Reserve free tickets online in advance for December weekdays. The museum is always free for children under 14.
Griffin Museum of Science and Industry
Address: 5700 S. Lake Shore Dr.
Special Exhibit: Christmas Around the World and Holidays of Light
The four-story Grand Tree anchors the holiday exhibit. Over 50 trees represent Chicago’s diverse communities and traditions.
The Holidays of Light exhibit celebrates global traditions. Chinese New Year, Diwali, Kwanzaa, and Hanukkah are featured.
Museum days balance outdoor activities in your Chicago December itinerary. They provide warm escapes when temperatures drop.
Shedd Aquarium
Address: 1200 S. DuSable Lake Shore Dr.
Free Evenings: December 2, 9, and 16 (5 to 9 PM, Illinois residents)
Over 32,000 sea creatures call Shedd Aquarium home. Beluga whales, sea otters, and sharks await your visit.
Reserve free tickets online in advance for December evenings. Regular admission uses plan-ahead pricing for savings.
https://www.sheddaquarium.org/
Field Museum
Address: 1400 S. DuSable Lake Shore Dr.
Free Days: Wednesdays throughout December (Illinois residents)
Sue the T-Rex is the museum’s most famous resident. Ancient Egypt exhibits and natural history collections fascinate visitors.
Chicago’s Essential Winter Foods
No visit is complete without trying Chicago’s iconic foods. These dishes warm you up from the inside out.
Deep Dish Pizza
Chicago’s signature dish features a buttery, flaky crust. Layers of cheese and chunky tomato sauce pile high.
Top spots to try: Lou Malnati’s (multiple locations), Pequod’s Pizza (Morton Grove and Lincoln Park), Giordano’s (multiple locations, including Navy Pier), Gino’s East (multiple locations), and Pizzeria Uno (29 E. Ohio St., the original location).
Plan for 45 minutes to an hour of baking time. Order drinks and appetizers while you wait.
Deep dish pizza is a must on any Chicago December itinerary. The hot, cheesy meal warms you after cold outdoor adventures.
Chicago-Style Hot Dogs
A beef frank in a steamed poppy seed bun. Yellow mustard, relish, onions, tomatoes, pickle spear, sport peppers, and celery salt complete it.
Portillo’s and Gene & Jude’s are local favorites. Never ask for ketchup on a Chicago hot dog.
Italian Beef Sandwiches
Thinly sliced, seasoned roast beef piles onto crusty Italian bread. Order it “wet” for extra jus or “dry” for less mess.
Al’s #1 Italian Beef and Mr. Beef are iconic spots.
Garrett Popcorn
The Chicago Mix combines sweet caramel and tangy cheddar. This addictive snack makes a perfect souvenir.
Multiple downtown locations offer quick service. Lines move faster than they appear.
https://www.garrettpopcorn.com/
Ice Skating Beyond Millennium Park
Chicago offers several unique skating experiences. Each location provides a different atmosphere and view.
Maggie Daley Park Skating Ribbon
Dates: November 14, 2025, through March 8, 2026
Address: 337 E. Randolph St.
The Skating Ribbon meanders through the park’s landscape. It’s twice the length of a traditional skating rink.
Skyscrapers and snow-dusted pine trees provide the backdrop. Reservations are required; book online in advance.
The Peninsula Sky Rink
Dates: November 21, 2025, through February 16, 2026
Address: 108 E. Superior St. (4th floor terrace)
This rooftop rink overlooks Michigan Avenue below. It’s the only hotel ice skating rink in Chicago.
Skate rental proceeds benefit children’s charities. Festive music and snowflake lighting enhance the experience.
The Peninsula Sky Rink adds romance to any couples’ Chicago December itinerary. Views of the Magnificent Mile lights are stunning.
https://www.peninsula.com/en/chicago/
Jack Frost Winter Pop-Up
Location: Fulton Market District
This two-acre winter wonderland comes from Jack’s Pumpkin Pop-Up creators. Multiple activities and attractions fill the outdoor space.
Ice skating, bumper cars, and curling are available. Axe throwing provides an unexpected winter activity.
Photo opportunities abound throughout the Christmas tree walk. Boozy hot cocoa and holiday cocktails warm visitors up.
New Year’s Eve in Chicago
Chicago hosts the first-ever Central Time countdown this year. Dick Clark’s New Year’s Rockin’ Eve broadcasts live from downtown.
Dick Clark’s New Year’s Rockin’ Eve
Date: December 31, 2025
Location: Chicago Riverwalk at Wacker Drive (Wells to Lake Street)
Time: Broadcast begins at 7 PM on ABC
Chance the Rapper hosts the Chicago celebration. Live performances lead up to the midnight countdown.
THE MART transforms into the backdrop for the countdown. Fireworks launch from bridges along the Chicago Riverwalk.
This is a historic first for the 55-year-old program. Chicago joins New York and Puerto Rico for live broadcasts.
https://www.choosechicago.com/articles/holidays/new-years-eve-celebrate-in-chicago/
Navy Pier Fireworks
The annual fireworks light up Lake Michigan at midnight. Views are available along the lakefront and from the pier.
Offshore Rooftop and Bar Sol host ticketed viewing parties. Dinner cruises offer unique vantage points for the display.
Practical Tips for December Visitors
Weather and Packing
December temperatures range from the low 20s to high 30s (Fahrenheit). Snow is possible but not guaranteed.
Pack a warm coat with a hood for wind protection. Layers are essential since indoor spaces are heated.
Warm hats, scarves, and gloves are necessary for outdoor activities. Waterproof boots help navigate slushy sidewalks.
Getting Around
The CTA provides excellent public transportation throughout Chicago. The “L” train connects downtown to most attractions.
Rideshare services like Uber and Lyft are widely available. Surge pricing may apply during peak holiday times.
Efficient transportation makes your Chicago December itinerary smoother. Download the Ventra app for easy CTA fare payment.
Booking Tips
Reserve museum tickets and skating sessions well in advance. Popular restaurants require reservations, especially for deep dish.
ZooLights and popular shows sell out early. Book theater tickets as soon as you confirm travel dates.
Free Mondays at ZooLights
Tickets for free Monday admission release one week prior. Set a reminder and book immediately when they become available.
How to Plan Your Chicago December Itinerary
Use this sample schedule to maximize your December visit. Adjust based on your interests and travel dates.
Day 1: Downtown Holiday Magic
Morning: Art Institute of Chicago (free weekdays in December)
Afternoon: Millennium Park, Christmas Tree, and The Bean
Evening: Christkindlmarket at Daley Plaza for glühwein and shopping
Day 2: Lakefront Attractions
Morning: Shedd Aquarium or Field Museum
Afternoon: Ice skating at Maggie Daley Park Skating Ribbon
Evening: Deep dish pizza at Lou Malnati’s or Pequod’s
Day 3: North Side Adventures
Afternoon: Lincoln Park Zoo (free daily)
Evening: ZooLights at Lincoln Park Zoo
Day 4: Cultural Experiences
Matinee: The Nutcracker at Lyric Opera House or A Christmas Carol at Goodman
Evening: Christkindlmarket Wrigleyville and explore the neighborhood
Day 5: Navy Pier and More
Afternoon: Winter WonderFest at Navy Pier
Evening: Centennial Wheel for skyline views; dinner at Giordano’s
This Chicago December itinerary balances indoor and outdoor activities perfectly. Book reservations early and dress warmly for the best experience.
