It’s not too soon to start making a list and checking it twice for what’s happening in Chicago this holiday season. Here are some suggestions from Choose Chicago.
HOLIDAY MARKETS
The Chicago Christkindlmarket is delighted to announce the return of its cherished holiday tradition for its 29th season at Daley Plaza in Chicago, its 4th year at RiverEdge Park in Aurora, and its return to Gallagher Way in Wrigleyville. The Chicago and Aurora locations will open on November 21, 2025, while Wrigleyville will welcome visitors starting November 23, 2025. All three markets are admission-free, featuring authentic vendors, live entertainment, and special events to create a festive holiday atmosphere.
HOLIDAY POP-UPS
- Jack Frost’s Pop Up – Returning November 2025
- Frosty’s – Returning November 2025
- Santa Baby – Returning November 2025
- Elf’d Up– Returning November 8, 2025
- Château Carbide Winter Garden at The Pendry Chicago (Launching Nov. 20 | 5 pm-12 am) – Château Carbide is launching their rooftop winter haven for another season with an all-new twist you won’t want to miss! Make a reservation for a private lodge and enjoy winter-inspired small bites and seasonal cocktails while taking in the stunning city-wide views of Chicago and all its snowy splendor.
HOLIDAY SHOWS & PERFORMANCES
- A Magical Cirque Christmas – November 25 – 30, 2025
- Holidazed and Amused: Naughty, Nice, and Everything In-Between at The Second City – November 26 – December 31, 2025
- Rudolph Runs Wild! at The Second City – November 28 – December 31, 2025
- It’s A Wonderful Life: Live in Chicago, American Blues Theater – Starts Friday, November 28, 2025
- A Black Ensemble Holiday Spectacular – Black Ensemble Theater – November 29 – December 24, 2025
- Elf The Musical – December 2 – 14, 2025
- Joffrey Ballet’s The Nutcracker – December 5–28, 2025
- Rocky Mountain High Experience®: A John Denver Christmas – December 12 – 14, 2025
- Manual Cinema’s Christmas Carol at the Fine Arts Building and Studebaker Theater – December 12-28, 2025
- Christmas with C.S. Lewis – December 16 – 21, 2025
- MANNHEIM STEAMROLLER CHRISTMAS BY CHIP DAVIS – December 20, 2025
- A Christmas Carol returns to the Goodman Theatre from November 15 – December 31, 2025
- Merry, Merry Chicago! – December 19-23, 2025, a series of concerts performed by the Chicago Symphony Orchestra
TOURS & ACTIVITIES
Bobby’s Bike Hike Holiday Hike: Season Sampling Food & Walking Tours begin at the end of November and run through Christmas Eve. See the lights of the Magnificent Mile, the ice skating rink and Christmas tree in Millennium Park, enjoy a warm and filling deep dish pizza, experience the German-inspired festivities of Christkindlmarket, and toast to a joyful season over a seasonal beverage! This 3 hour Chicago holiday tour is perfect for families, friends, holiday parties, and anyone looking to celebrate the season in an exciting new way. All food & non-alcoholic beverage samples included in ticket price. (Pricing starts at $74.99.)
Chicago Boat Company’s Hot Tub Boats, returning this winter with their launch in November (exact timeline and hours to come). Departing from Marina City (300 N. State St.), guests can take out a Hot Tub Boat for up to 90 minutes with as many as six guests per boat. They’ll cruise along the Chicago River, taking in iconic skyscraper views and, in December, the city’s festive décor and holiday cheer from river level. Each boat comes equipped with a Bluetooth speaker and is BYOB, with plenty of cooler space and floating cup holders. Hot chocolate, hot apple cider, mulled wine, you name it!
The Christmas Tree Crawl: The Magic of Chicago at the Holidays – Let Inside Chicago Walking Tours take you on an enchanting stroll through the heart of the city at its prettiest time — during the winter holiday season. On this nostalgic and educational tour, we will lead you on a “Christmas treasure hunt” through downtown Chicago in search of the most stunning and impressive Christmas trees and other holiday decorations — and we know where they are! This tour includes not only visits to well-known stops like the Christkindlmarkt and the old Marshall Field’s, but also to little-known stops that contain some of the best holiday decorations downtown. You’ll learn about the origins of some world-famous Christmas characters — some of them from Chicago, some not — as well as the history behind Christmas traditions practiced by people around the world. [November 28 – December 20, 2025; available Thursdays-Saturdays]
- We call this tour a “pop-up tour” because it’s offered for a limited time, because we want to show off the city’s beauty at this time of year. You won’t find a boat, a bus, or even a segway where we’re going.
It’s the most wonderful time of the year! Chicago’s most unique and beloved holiday tradition is here: The Allstate CTA Holiday Fleet. Now in its 33rd year of operation, we are excited to be delivering holiday cheer throughout Chicago’s neighborhoods and welcome you aboard our decked-out and dazzling Allstate CTA Holiday Train and the popular Allstate CTA Holiday Bus!
About Choose Chicago
Choose Chicago is the official sales and marketing organization responsible for promoting Chicago as a global visitor and meetings destination, leveraging the city’s unmatched assets to ensure the economic vitality of the city and its member business community. Follow @choosechicago on Facebook, Instagram, Twitter, LinkedIn, and TikTok. For more information, visit choosechicago.com.
