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Chicago Winter Bucketlist! ☃️🧣
10
items Here’s a top 10 winter bucket-list for Chicago — many of these are perfect for your lifestyle covering food, experiences, travel, and lifestyle!
Sections
3
Markets
Experiences
Food & Drink
Markets
The iconic Christkindlmarket: with 3 different locations (Daley Plaza, Aurora, and Wrigleyville)
The Christkindlmarket Chicago is a German-style outdoor holiday market held each winter in downtown Chicago at Daley Plaza (50 W Washington St). It features vendor huts selling artisan gifts, German-inspired food (bratwurst, pretzels, etc.), hot spic...
Christkindlmarket Chicago
Experiences
Make the most of Chicago’s winter season with unforgettable experiences that bring the city to life — sparkling lights, ice skating under the skyline, and cozy indoor escapes. These are the must-do moments that define winter in the city.
ZooLights at Lincoln Park Zoo is one of Chicago’s most magical winter traditions, transforming the historic zoo into a sparkling wonderland of over 2.5 million lights. From late November through early January, visitors can stroll through glowing tunn...
Lincoln Park Zoo Lights
Opens November 21st!
One of the most iconic winter experiences in Chicago: the outdoor rink in Millennium Park, right by the skyline and the famous “Bean”. It’s free admission (you pay for skate rental and just need a reservation) and well-set for ...
Millennium Park Ice Rink
Opens November 14th!
A more playful, scenic ice-skating alternative: the Skating Ribbon in Maggie Daley Park offers curves, gentle elevation changes and great city views. 
Content tip: Show the motion of the ribbon, maybe a POV clip of skating th...
Maggie Daley Park Ice Skating Ribbon
On November 21st! Pre-show at 5 p.m.; Tree lighting around 6:25 p.m.
The City of Chicago Christmas Tree Lighting Ceremony marks the official start of the holiday season in the heart of Millennium Park. On Friday, 11/21, join locals and visitors alik...
City of Chicago Christmas Tree Lighting Ceremony
The Wintrust Magnificent Mile Lights Festival is one of Chicago’s most anticipated holiday celebrations, returning on Saturday, November 22, 2025. Festivities begin at 11 a.m. at Lights Festival Lane in Pioneer Court, where guests can enjoy family-fr...
The Wintrust Magnificent Mile Lights Festival
The CTA Holiday Train is one of Chicago’s most joyful and unique holiday traditions, bringing festive cheer to every corner of the city. From late November through December, the “L” trains are transformed with thousands of twinkling lights, holiday m...
Allstate CTA Holiday Train & Bus - Chicago
Food & Drink
Discover Chicago’s most delicious spots — from cozy winter rooftops and festive pop-ups to hidden gems and must-try seasonal menus. Whether you’re craving comfort food, a picturesque brunch, or elevated cocktails with skyline views, these are the pla...
The Winter Igloos at LondonHouse Chicago are one of the city’s most enchanting cold-weather experiences. Set high above the skyline on the rooftop terrace, these cozy, clear-domed lounges offer panoramic views of the Chicago River, the Wrigley Buildi...
Rudolph's Rooftop Winter Igloos at LondonHouse Chicago
The Butch McGuire’s Christmas Pop-Up is a Chicago holiday institution, transforming the classic Gold Coast pub into a festive wonderland each winter. Starting in late November, the entire bar is decked out with thousands of twinkling lights, ornament...
Butch McGuire's
The Walnut Room at Macy’s on State Street is one of Chicago’s most cherished holiday traditions, offering an elegant and nostalgic dining experience beneath its iconic 45-foot Christmas tree. Established in 1907, it was the first restaurant ever open...
The Walnut Room
