Looking for the best things to in Chicago during the holiday season? Here are the best things to do in Chicago for Christmas and during the entire holiday season that are guaranteed to get you into the holiday spirit!
Things to Do in Chicago During Christmas
I think that Christmas and the holiday season is one of the best times of the year in Chicago. Many festive events and activities take place in Chicago during the holiday season including holiday lights, tree lightings, holiday shopping, christmas markets and more!
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Visit an Outdoor German-Style Christmas Market
Christkindlmarket is an authentic German-style outdoor market. Visitors can shop for Christmas ornaments and products from around the world and try various German food and drinks such as roasted nuts, fresh pretzels, bratwurst, and hot spiced wine. You can also purchase a limited edition souvenir mug to remember your trip. There are two locations in the city (downtown and Wrigleyville) and there is also a location in the suburbs in Aurora, Illinois.
Where: Daley Plaza, 50 W Washington St, Chicago, IL 60602 and Gallagher Way, 3635 N Clark St, Chicago, IL 60613.
When: Daley Plaza: November 21 – December 24, 2025; Wrigleyville: November 23 – December 31, 2025.
Cost: Admission is FREE.
See the Giant City of Chicago Christmas Tree
See Chicago’s “official” Christmas tree at Millennium Park during the holiday season. The best time to see it is in the evening when it is lit up.
Make sure to stop by The Bean – a must on any Chicago bucket list. The Bean is located a few feet away from the tree and can even take photos of The Bean with the Christmas tree in the background.
When: The tree will be lit up on November 22, 2025 and will stay at Millennium Park until early January
Where: Millennium Park, near the intersection of Michigan Ave. and Washington St.
Cost: Free.
Join a Christmas Eve Gourmet Dinner Cruise on Lake Michigan
Looking for a unique meal on Christmas Eve? Join a Christmas Eve gourmet dinner cruise on Lake Michigan. Enjoy a gourmet 3-course plated dinner with views of Chicago’s skyline, creative cocktails and DJ entertainment.
Attend a Christmas Themed Candlelight Concert
Chicago’s Candlelight Concerts is a series of special classical music concerts that take place in beautiful venues bathed in candlelight. Some of the concerts taking place this holiday season include:
Christmas Carols on Strings
Holiday Carols on Strings
Christmas Pop Classics
Christmas Special Featuring “The Nutcracker” & More
You can find the full list of candlelight concerts in Chicago here.
AirOtic Naughty Noël
This holiday season, treat yourself to a night like no other with Naughty Noël, the sensual Christmas spectacular from Airotic Soirée. Combining world-class acrobatics, hypnotic burlesque, and festive fantasy, this one-of-a-kind cirque cabaret transforms the holiday spirit into an intoxicating celebration of desire, joy, and playfulness. Step into a wonderland of sensual snowflakes, daring elves, and gravity-defying performers who will dazzle you with passion and power. 21+ with valid ID.
When: December 6, 2025 – January 3, 2026
Where: Experience 868, 868 N Franklin St, Chicago, IL 60610
Cost: Price varies. Click here for full prices and to purchase tickets in advance.
Santa’s Secret Immersive Holiday Experience
At Santa’s Secret Immersive Holiday Experience, you’ll make your way through a winter wonderland with immersive holiday installations along a winding path into Santa’s secret speakeasy. Enjoy Christmas-themed cocktails, food, a live band, and a variety of performances (including aerial acts, ballet, burlesque and more), all with a holiday twist. Must be 18+ to enter and 21+ with a valid ID to drink.
When: November 28 – December 31, 2025 (select dates)
Where: Pioneer Court, 401 N Michigan Ave, Chicago, Illinois 60611
Cost: Prices start at $45 per person for general seating. Click here to see prices and purchase tickets.
Passport to Santa
Step into the North Pole with Passport to Santa, an interactive holiday adventure where every child becomes a traveler on a festive quest. Along the way, they’ll sign the Naughty or Nice List with Mrs. Claus, build toys in Santa’s Workshop, train with Rudolph, race in the Gingerbread Tower Challenge, test their strength in Nutcracker Kingdom, dunk the Grinch, and write wishes with the Christmas Angel. Each completed activity earns a stamp in their passport, which can be redeemed during a personal visit with Santa himself for exclusive access to his Christmas Carnival — complete with obstacle courses, bounce houses, festive arts & crafts, and an array of holiday carnival games.
When: November 29 – December 31, 2025 (select dates)
Where: Pioneer Court, 401 N Michigan Ave, Chicago, Illinois 60611
Cost: Prices start at $35 per person. Click here to see prices and purchase tickets.
Take a Holiday Tour
If your time in Chicago is short, there are a few tours that focus on Chicago’s holiday attractions:
Guided Holiday Walking Tour and Food Sampling
Seasonal Stroll Walking Tour of Holiday Attractions
BYOB Party Bus Holiday Lights Tour
ZooLights at Lincoln Park Zoo
ZooLights Presented by Invesco QQQ and ComEd at Lincoln Park Zoo is a cheerful, family-friendly holiday event in the heart of the city. Zoolights features hundreds of luminous LED displays and seasonal experiences, all under the glow of millions of lights.
Where: Lincoln Park Zoo, 2400 N. Cannon Drive, Chicago, IL
When: November 21, 2025–January 4, 2026
Cost: $7–$12 depending on the day (free admission on Mondays)
See the Crèche and Wreathed Lions at the Art Institute of Chicago
The Art Institute of Chicago is a must on any Chicago bucket list year round but there are more reasons to visit during the holiday season.
Beginning Friday after Thanksgiving the museum’s lions will be decked with their evergreen wreaths for the holiday season.
Through January 5, 2026, you can also see the Art Institute’s spectacular 18th-century Neapolitan crèche, or Nativity scene, telling the story of Jesus Christ’s birth through more than 200 painted terracotta figures staged in an elaborate environment inspired by 18th-century Naples.
Hours: Monday and Friday–Sunday from 11 a.m.– 5 p.m. Thursdays from 11 a.m.– 8 p.m. The museum is closed on Tuesdays & Wednesdays as well on Thanksgiving, Christmas, and New Year’s Day.
Where: 111 S Michigan Ave, Chicago, IL 60603
Cost: Price varies by age; members and children under 14 are always free. There are discounts for Chicago and Illinois residents. Click here to buy a skip the line ticket if you want to avoid long lines.
Christmas Around the World and Holidays of Light
The Christmas Around the World and Holidays of Light at the Griffin Museum of Science and Industry annual celebration began in 1942 and features a four-story, floor-to-dome Grand Tree, surrounded by a forest of more than 40 trees and displays which represent the holiday traditions from cultures around the globe.
Where: Griffin Museum of Science and Industry, 5700 S Lake Shore Drive.
When: Through January 5, 2026
Cost: Christmas Around the World and Holidays of Light is included in regular museum admission. You can purchase a skip the line ticket here.
Tip: If you are visiting a few museums, consider purchasing a Chicago CityPASS or Go Chicago Card to save money on entrance fees.
Winter WonderFest at Navy Pier
Winter WonderFest at Navy Pier is an indoor holiday experience, complete with dazzling décor, thrilling rides, ice skating, and seasonal fun for all ages.
Other fun attractions at Navy Pier include the (large Ferris wheel, Flyover Chicago and the Chicago Children’s Museum.
Where: Navy Pier (600 E Grand Ave, Chicago, IL 60611)
When: December 5, 2025-January 4, 2026
Go Outdoor Ice Skating
One of the best and picture perfect spots to go ice skating in Chicago is the McCormick Tribune Ice Rink right in front of The Bean. Admission is free, but online reservations are required.
Another popular option is the skating ribbon at Maggie Daley Park which has a path twice the length of a lap around a traditional skating rink. Tickets will be released on a rolling basis at (noon) every 2 weeks.
Here is a list of the best outdoor ice skating rinks in Chicago with hours, prices and other information.
Ride the CTA Holiday Train and Bus
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The CTA Holiday Train is a holiday tradition unique to Chicago. As the train pulls into each station, Santa waves to riders from his sleigh on an open-air flatcar carrying his reindeer and decorated holiday trees. Each car of the train is wrapped with holiday and seasonal images. Thousands of twinkling lights outline the shape of the train and windows, with even more lights running across the tops of the cars. (The video above is from one of my favorite Chicago photo spots.)
The CTA Holiday Bus is 60-foot bus turned into a winter wonderland with holiday music playing and Santa waving and from the roof-hatch of the bus. The exterior of the bus features Chicago’s skyline one snowy evening with “Ralphie the Reindeer” leading the way, his nose aglow and Santa’s sleigh in tow. Festive strings of lights outline the bus and its windows, along with sparkling snowflakes that light-up at night.
When: The holiday bus runs from November 25-December 20, 2025 and the holiday train runs from November 29-December 22, 2025. See transitchicago.com/holidayfleet for full details on routes, dates and times.
Cost: Regular CTA fare. See transitchicago.com for prices. You can see the bus pass by for free from the street.
Dine at the Walnut Room
Dining at the Walnut Room is a legendary Chicago holiday tradition. Located on the 7th floor of Macy’s State Street (formerly Marshall Fields), the Walnut Room was the first restaurant ever opened in a department store. During the holiday season diners can enjoy the view of the Macy’s “Great Tree” in the middle of the restaurant while feasting on holiday classic dishes such as Mrs. Hering’s 1890 Original Chicken Pot Pie.
If you cannot get reservations, there is a selfie spot located right outside of the restaurant with a view of the tree that makes for a good photo opportunity.
Where: 7th floor at Macy’s State Street at 111 N. State Street, Chicago, IL
Go Holiday Shopping (or Window Shopping)
Chicago is a great city for shopping with every type of store you can imagine. Many shopping centers and departments stores have holiday decorations and attractions to put you in a festive mood. Make sure not to miss Macy’s State Street (formerly Marshall Fields) – the building is a National Historic Landmark and it is known for its holiday window displays.
The major shopping areas in downtown Chicago include State Street (where you can find Macy’s, Target and many smaller stores) and The Magnificent Mile (where you can find three shopping centers, luxury designers and labels, several departments stores and popular brands).
If you are looking for unique and/or handmade items, check out these holiday markets: Millennium Park Holiday Market (November 21-22, 2025), Chicago Artisan Market @ Ravenswood (November 29-30, 2025), One of a Kind Show (December 4-7, 2025), Sauced The Night Market Before Xmas (December 12-13, 2025), Chicago Artisan Market @ Fulton Market (December 14, 2025) and Renegade Craft Fair (December 20-21, 2025).
Drink Glogg at Simon’s Tavern
Drinking the signature glögg (mulled wine) at Simon’s Tavern is a holiday tradition for Chicagoans.
The long standing neighborhood dive bar in Andersonville is packed every year during the holiday season.
Where: Simon’s Tavern, 5210 N Clark St
Drink at a Christmas Themed Pop-Up Bar
Chicago has several holiday pop-up bars that open just for the holiday season. These bars offer holiday decorations, themed cocktails and snacks and more festive touches. Advance reservations are recommended as they tend to be very popular. Some of the best holiday themed bars include:
Nutcracker Bar & Hotel (100 E Chestnut St)
Frosty’s Bar (809 W Evergreen Ave)
Santa Baby Bar (3505 N Clark Street)
Elfd’d Up (Stretch Bar & Grill, 3485 N. Clark Street)
See a Christmas Show
Get in the holiday spirit with a Christmas show. There are many holiday shows you can see in Chicago this year, including:
Elf the Musical
‘Twas the Night Before… by Cirque du Soleil
Joffrey Ballet – The Nutcracker
Ballet Chicago’s The Nutcracker
A Christmas Carol at the Goodman Theatre
The Holiday in Concert
Chicago Symphony Orchestra – Home Alone in Concert
This is a great list of all the holiday shows in Chicago.
Walk the Illuminated Light Trail at Lightscape
Lightscape is an after-dark, illuminated trail with thousands of twinkling lights at the Chicago Botanic Garden. Ok so this is technically not in Chicago but it is in the suburbs only a 30 minute drive from downtown.
When: Through January 4, 2026
Where: Chicago Botanic Garden, 1000 Lake Cook Road, Glencoe, IL 60022 (24 miles north of downtown Chicago)
Illumination: Tree Lights at The Morton Arboretum
Illumination: Tree Lights at The Morton Arboretum is a one-of-a-kind, interactive spectacle of color, light, and sound that has been delighting audiences since 2013. Be surrounded by color as you walk a one-mile paved path amid interactive lighting effects that highlight the beauty of trees in winter.
When: Through January 3, 2026
Where: Morton Arboretum, 4100 Illinois Route 53, Lisle, IL 60532 (28 miles west of downtown Chicago)
Millennium Park Holiday Sing-Alongs (previously “Caroling at Cloud Gate”)
Join the Millennium Park Holiday Sing-Along (previously “Caroling at Cloud Gate”) to sing out and celebrate Chicago’s diverse holiday traditions on Friday evenings in December.
When: December 5, 12 & 19, 2025, 6pm
Where: Millennium Park, Grainger Plaza, Cloud Gate
Cost: Free Admission.
Chicago Christmas and Holiday Events
City of Chicago Christmas Tree Lighting Ceremony
The City of Chicago Christmas Tree Lighting Ceremony kicks off the holiday season.
When: The lighting ceremony takes place Friday, November 21, 2025. Pre-show at 5 p.m.; Tree lighting around 6:25 p.m. (Plan to Arrive Early)
Where: Millennium Park, Near Washington St. & Michigan Ave. Enter Park through the South Promenade on Monroe Street.
Cost: Free.
Magnificent Mile Lights Festival
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The Magnificent Mile Lights Festival is a popular family friendly live parade (the largest nighttime parade in the US) when one million lights are illuminated on the trees along The Magnificent Mile. Led by Mickey Mouse and Minnie Mouse of The Walt Disney World Resort, the parade features fabulous floats, giant helium balloons, marching bands, celebrities, musical performances, Santa Claus, fireworks and more. This year’s holiday event will feature a new Chicago River lighting spectacle and the tallest balloon ever.
Tip: Streets around the parade route close to car traffic a few hours before the parade, so prepare to take the train or book a hotel nearby.
When: Saturday, November 22, 2025
Where: The parade is on North Michigan Avenue from Oak Street to Wacker Drive.
Cost: Free.
More Chicago Holiday Themed Events 2025
In addition to the events mentioned above, other festive holiday themed events and activities include: Chicago Thanksgiving Parade (November 27, 2025), A Flamenco Christmas – The Newberry Consort (December 5-7, 2025), Ravenswood Light Up Nights Festival & Holiday Market (December 6, 2025), Chicagoland Toys For Tots Motorcycle Parade (December 7, 2025), Santa Hustle 5K (December 6, 2025), Adults Night Out: Holidaze at Lincoln Park Zoo (December 11, 2025) and TBOX (Twelve Bars of Christmas) Bar Crawl (December 13, 2025).
As you can see there are many things to do in Chicago during Christmas and the holiday season.
Planning a trip to Chicago? Check out my Chicago guides and itineraries:
- 3 Days in Chicago Itinerary + Travel Tips From a Local
- The Perfect Itinerary for One Day in Chicago
- Most Instagrammable Places in Chicago
#chicago #holidays
