YOUR CHICAGO GUIDE TO THE HOLIDAYS
There's no shortage of holiday cheer in Chicago, and Staypineapple Chicago puts you right in the middle of it! From festive events and seasonal experiences to local bars and restaurants serving up a little extra holiday spirit, there's plenty to explore just steps or a short ride away. Grab your favorite people (or enjoy a little solo time), check out our guide and get ready to make holiday memories worth sharing!
Photo by Rezal Scharfe on Unsplash
Experiences to Bring the Holiday Magic to Life
Lincoln Park ZooLights (12-minute drive from Staypineapple Chicago)
Where: 2400 N. Cannon Drive
When: November 20, 2026–January 3, 2027, from 4–9:30 p.m.
Explore dazzling light displays, glowing tunnels and festive decorations at the zoo.
Winter Flower Show (15-minute drive from Staypineapple Chicago)
Where: 300 N. Central Park Ave
When: November 25, 2026–January 3, 2027
Enjoy a colorful display of seasonal blooms at the Garfield Park Conservatory.
Christmas Around the World and Holidays of Light (20-minute drive from Staypineapple Chicago)
Where: 5700 S. DuSable Lake Shore Dr
When: November 7, 2026–January 3, 2027
See the Griffin Museum of Science and Industry’s beloved four-story Grand Tree surrounded by more than 50 trees and displays representing holiday traditions from around the world.
Music Box Christmas Sing-A-Long & Double Feature (15-minute drive from Staypineapple Chicago)
Where: 3733 N. Southport Ave
When: December 5–24, 2026
As one of the most popular and beloved Christmas traditions in Chicago, catch holiday classics It's a Wonderful Life and White Christmas on the big screen
Christkindlmarket at Daley Plaza | Photo by Olivia Lee
Christkindlmarket (4-minute walk from Staypineapple Chicago)
Where: 50 W. Washington St
When: November 20–December 24, 2026
Shop festive stalls filled with holiday gifts, ornaments, European treats and warm drinks at this joyful German-inspired Christmas market in Daley Plaza.
Millennium Park Chicago, Photo by Vincent Y @USA on Unsplash
City of Chicago Christmas Tree (5-minute walk from Staypineapple Chicago)
Where: Michigan Ave. & Washington St.
When: November 20, 2026–January 10, 2027
Admire Chicago’s iconic Christmas tree and snap a festive photo during your visit to Millennium Park.
Ice Skating Rink Chicago, Photo by Jeren Emlano on Unsplash
Ice Skating Ribbon (4-minute drive from Staypineapple Chicago)
Where: 337 E. Randolph St
When: November 13, 2026–March 7, 2027
Lace up your skates and glide around the winding, quarter-mile ice trail at Maggie Daley Park surrounded by Chicago’s festive downtown scenery.
Holidays @ Skydeck Chicago (5-minute drive from Staypineapple Chicago)
Where: 233 S. Wacker Dr
When: November 13, 2026–January 4, 2027
Take in spectacular views of the city from 103 floors up with twinkling lights and holiday decor, and step out onto The Ledge for Santa photos!
Photo by Tobias Reich via Unsplash
The Marshall Field’s Walnut Room (2-minute walk from Staypineapple Chicago)
Where: 111 N. State St
When: November 2, 2026–January 17, 2027
Enjoy a special holiday menu at this iconic Chicago restaurant, known for its grand holiday tree, elegant setting and seasonal charm.
Festive Bars & Restaurants to Get Into the Holiday Spirit
Holiday Cheers, Photo by Mai Sakura via Unsplash
Christmas at Butch McGuire’s (15-minute walk from Staypineapple Chicago)
Where: 20 W. Division St.
When: Mid-November 2026–New Year’s Eve 2026
Santa Baby Christmas Bar (20–25-minute drive from Staypineapple Chicago)
Where: 3505 N. Clark St.
When: Nov. 20, 2026–Jan. 3, 2027
Frosty’s Christmas Pop-Up Bar (15-minute walk from Staypineapple Chicago)
Where: 15 W. Illinois St.
When: November 21, 2026
Christmas Club (20–25-minute drive from Staypineapple Chicago)
Where: 3460 N. Clark St., Wrigleyville
When: Nov. 22, 2026–mid-January 2027
Holly Jolly Christmas Bar at Everything Bar (10-minute drive from Staypineapple Chicago)
Where: 1601 W. Grand Ave.
When: Nov. 12–Dec. 27, 2026
Sweets with Santa at RPM Steak (15-minute walk from Staypineapple Chicago)
Where: 66 W. Kinzie St.
When: Dec. 19, 2026