What to Do in Chicago This Christmas Weekend
The holiday season transforms Chicago into a winter wonderland. Whether you're a lifelong Cubs fan or visiting for the weekend, Chicago offers countless ways to celebrate, with Wrigleyville at the heart of the action.
Here's your complete guide to making the most of a Christmas weekend in the Windy City.
Friday Evening: Winterland Magic
Arrive at Gallagher Way
Start your Christmas weekend at Winterland at Gallagher Way, running through December 31. Friday hours extend from 11 a.m. to 10 p.m., but arriving in the evening lets you experience the lights at their most magical.
Shop Christkindlmarket Wrigleyville
Head to Christkindlmarket Wrigleyville for authentic German treats. Sip hot Glühwein (mulled wine) while browsing candy cane-striped wooden huts filled with handcrafted ornaments, local art and holiday treasures. Admission to Gallagher Way and the market is free.
Skate and Ride
Lace up at the Gallagher Ice Rink for $8 with your own skates or $16 with rentals. The rink stays open through February 15, 2026. After skating, take the Holiday Train that circles the Wrigley Field concourse for $5 per ride, offering unique views of the iconic ballpark.
Meet Santa
Stop by Santa's Workshop between 4 p.m. and 9 p.m. A photographer will be on site, or bring your own camera. Santa's Workshop is completely free. Warm up with hot chocolate and seasonal treats before heading out.
Saturday Morning: Downtown Traditions
Chicago's Christmas Tree
Wake up Saturday and head to Millennium Park where Chicago's official Christmas tree stands near Michigan Avenue and Washington Street. The 68-foot Norway spruce remains illuminated through January 11.
Millennium Park Ice Skating
The McCormick Tribune Ice Rink opens at 11 a.m. for free skating sessions with Cloud Gate (The Bean) as your backdrop. Reservations are required, and skate rentals start at $17.
Holiday Market Shopping
Browse the Millennium Park Holiday Market from noon to 5 p.m., where more than 40 local artisans showcase jewelry, pottery and unique holiday gifts. Grab a warm beverage from Millennium Hall along the Chase Promenade North.
Saturday Afternoon: Magnificent Mile
Festival Activities
Make your way to Michigan Avenue for the Wintrust Magnificent Mile Lights Festival. Festivities begin at 1 p.m. at Pioneer Court with performances, Santa photo ops and family activities.
Parade and Fireworks
The Magnificent Mile Lights Parade steps off at 5:30 p.m. from Oak Street. More than one million lights illuminate over 200 trees along Michigan Avenue as giant balloons, Disney characters and marching bands make their way south. The celebration culminates in a spectacular fireworks display over the Chicago River at approximately 7:15 p.m.
Back to Wrigleyville
Head back to Wrigleyville for dinner at neighborhood restaurants before returning to Winterland. Saturday hours at Gallagher Way extend until 10 p.m., giving you time to ride the carousel, play carnival games or warm up by the firepits.
Sunday: More Holiday Fun
Pets Welcome
Start Sunday with breakfast in Lakeview before heading to Winterland (11 a.m. to 7 p.m.). Sundays are special because pets are welcome at Santa's Workshop from 11 a.m. to 5 p.m., so bring your four-legged family members for holiday photos.
Explore More Markets
The Christkindlmarket Downtown at Daley Plaza (50 W. Washington St.) offers another authentic German market experience through December 24, with wooden huts, traditional food and special souvenir mugs.
ZooLights Experience
ZooLights at Lincoln Park Zoo runs through January 4 with more than three million lights across the zoo grounds. Admission is affordable and even free on Mondays. Enjoy interactive displays, carolers, ice carving demonstrations and the bilingual Zooltide light show with cozy treats like hot cocoa and s'mores by the fire.
Holiday Dinner
End your weekend with dinner at the Walnut Room inside Macy's on State Street, where the Great Tree has been a holiday tradition since 1907. Reservations are recommended several months in advance.
Getting Around
Public Transportation
The CTA Red Line Addison stop puts you steps from Gallagher Way. For downtown events, multiple CTA lines stop near Millennium Park and Michigan Avenue.
Parking Options
Parking at Winterland is available at the Toyota Camry Lot (1126 W. Grace St.) starting at $15 or the Toyota Highlander Lot (1088 W. Waveland Ave.) for $30 on select days. Purchase parking through the Cubs tickets website or pay on site, subject to availability.
Why Wrigleyville Celebrates Best
The neighborhood surrounding the Friendly Confines comes alive during the holidays with twinkling lights and festive décor. Walk past the historic Wrigley Field Marquee at Clark and Addison streets, adorned with holiday touches. Stop by Lucky Dorr in Caretakers Way for seasonal beers and hot cider during extended Winterland hours.
The energy that fills Wrigley Field during the season transforms into holiday spirit each winter, proving this neighborhood celebrates every season with passion.
Christmas in Chicago offers something for everyone, from Cubs fans who call Wrigleyville home to visitors experiencing the city's holiday magic for the first time. Whether you're skating under the lights at Millennium Park, shopping at authentic German markets or riding the Holiday Train around Wrigley Field, you'll create memories that last long after the season ends.
Bundle up, bring your holiday spirit and get ready to experience why Chicago winters are worth celebrating.
Frequently Asked Questions
When does Winterland at Gallagher Way open?
Winterland runs November 23 through December 31, with regular hours Monday through Thursday from 3 p.m. to 9 p.m., Friday and Saturday from 11 a.m. to 10 p.m. and Sunday from 11 a.m. to 7 p.m. Special hours apply for Thanksgiving, Christmas Eve and New Year's Eve. The Gallagher Ice Rink stays open through February 15, 2026.
How much does it cost to visit Winterland?
Admission to Gallagher Way and the Christkindlmarket Wrigleyville is free. Holiday Train rides cost $5, Gallagher Ice Rink access is $8 with your own skates or $16 with rentals, and food, beverages and souvenirs are available for purchase. Santa's Workshop photos are free with your own camera.
Where is the Chicago Christmas tree located?
Chicago's official Christmas tree stands in Millennium Park near the intersection of Michigan Avenue and Washington Street. The 68-foot Norway spruce remains illuminated through January 11, 2026. Millennium Park is accessible daily, and viewing the tree is completely free.
Can I bring my pet to Winterland?
Pets are welcome at Santa's Workshop on Sundays only from 11 a.m. to 5 p.m. Service animals are always welcome throughout Gallagher Way.
Is ice skating free at Millennium Park?
Admission to the McCormick Tribune Ice Rink at Millennium Park is free, but reservations are required. Skate rentals start at $17. Free skating lessons are available on weekends, made possible by the McDonald's Active Lifestyles Endowment managed by the Millennium Park Foundation.
What's the best way to get to Wrigleyville for Winterland?
The CTA Red Line Addison stop puts you right at Wrigley Field and Gallagher Way. If driving, parking is available at the Toyota Camry Lot starting at $15 or the Toyota Highlander Lot for $30 on select days. Purchase parking in advance through the Cubs website or pay on site.