Chicago’s holiday season reaches peak magic this weekend. Markets, musicals, and festive lights await across the city.
Looking for things to do in Chicago this weekend? Three days of holiday fun start Friday and run through Sunday.
Whether you’re planning a family outing or date night, we’ve covered it. Here’s everything worth doing December 12 through 14.
Christkindlmarket: Chicago’s Must-Visit Holiday Market
Christkindlmarket remains the crown jewel of Chicago’s holiday season. Two locations offer German-style shopping, food, and festive atmosphere.
The Daley Plaza location anchors downtown at 50 W. Washington. Wooden vendor huts sell handcrafted ornaments, toys, and imported gifts.
Kids love the hot chocolate while parents enjoy warm glühwein. Boot-shaped souvenir mugs make the experience even more memorable.
The Wrigleyville location at Gallagher Way offers a similar experience. It’s more nightlife-adjacent with surrounding bars and restaurants nearby.
Admission is free at both locations throughout the weekend. Budget your spending on food, drinks, and gifts as desired.
Holiday Shows and Performances
Elf the Musical brings Buddy’s story to the Auditorium Theatre stage. Shows run through December 14 at 50 E. Ida B. Wells Dr.
This upbeat adaptation works for all ages in your group. Expect singable songs and plenty of laughs throughout the show.
The Phantom of the Opera returns to Chicago for 2025–26. The Cadillac Palace Theatre hosts this Broadway classic all weekend.
Theater lovers searching for things to do in Chicago this weekend won’t find better options. Book tickets immediately as popular showtimes sell out fast.
Ice Skating at Millennium Park
Ice skating at McCormick Tribune Ice Rink never disappoints visitors. The Millennium Park location offers stunning skyline views while you glide.
Skating is free if you bring your own skates along. Rentals are available at low cost for those traveling light.
The rink operates all weekend, weather permitting of course. Arrive early to avoid the longest wait times on Saturday.
Holiday Markets Beyond Christkindlmarket
The SAUCED Night Market returns with a holiday edition this weekend. The Chicago Athletic Association Hotel at 12 S. Michigan Ave. hosts.
Local makers, food vendors, and DJs create a lively atmosphere. Friday and Saturday nights draw social crowds looking to mingle.
Cocktails and late-night bites make this perfect for couples. Early evening hours work well for families before bedtime arrives.
Randolph Street Market runs its Holiday Market Festival Saturday and Sunday. Plumbers Hall at 1350 W. Washington Blvd. fills with unique finds.
Vintage treasures, handmade crafts, and artisan décor line the aisles. This is your spot for one-of-a-kind holiday gifts.
Anyone asking things to do in Chicago this weekend should add these markets. They offer experiences you won’t find at typical mall shopping.
Nightlife and Bar Crawls
Winter cocktail crawls pop up across popular neighborhoods this weekend. River North, Wicker Park, Lakeview, and West Loop all host events.
Check Eventbrite for organized bar-hop routes on Friday and Saturday. Groups of friends will find plenty of festive crawl options.
Christkindlmarket Wrigleyville pairs perfectly with neighborhood bar-hopping afterward. The 3635 N. Clark St. location stays open late on weekends.
Free Activities This Weekend
The Millennium Park Holiday Sing-Along happens Friday at 6 PM. This free community event takes place near Cloud Gate.
Join fellow Chicagoans celebrating global holiday traditions through song. The Bean provides the perfect backdrop for this annual gathering.
Chicago’s holiday lights transform entire neighborhoods into wonderlands. Create your own walking tour through illuminated streets this weekend.
Michigan Avenue’s Magnificent Mile sparkles from end to end. State Street, Wrigleyville, and Fulton Market also deliver impressive displays.
The Chicago Cultural Center offers free exhibits all weekend long. Rotating art and cultural installations fill 78 E. Washington St.
This Beaux-Arts landmark features the world’s largest Tiffany dome. Warm up inside while exploring Chicago’s cultural offerings completely free.
Things to Do in Chicago This Weekend: Planning Tips
Friday evening works best for the Holiday Sing-Along and SAUCED market. Saturday offers the most options across all activity types.
Sunday brings lighter crowds at Christkindlmarket and Randolph Street Market. Use it for relaxed browsing before the work week begins.
Layer up and check weather forecasts before heading out daily. Chicago’s December temperatures require warm coats, hats, and gloves.
Book Elf the Musical and Phantom tickets online right now. This weekend packs enough holiday spirit to last all month.
