Plan your holiday adventure in Chicago Loop with our comprehensive event guide. Whether you're rediscovering Chicago Loop or falling in love with it for the first time, our guide maximizes your festive experience.
One highlight of the season is the Christkindlmarket, a charming German-style Christmas market where you can explore festive stalls offering handmade ornaments, delicious treats, and warm drinks. Another must-see event features the dazzling holiday lights along Michigan Avenue as part of the Magnificent Mile Lights Festival, transforming the city into a twinkling winter wonderland. And the Christmas Tree Lighting at Millennium Park is something you definitely don't want to miss, showcasing a stunning tree accompanied by delightful holiday music. See more details on these and other fun events and activities below!
Happy Holidays!
Top Events Events In and Around Chicago Loop
- The Hip Hop Nutcracker (Chicago)
- Chicagoland Toys for Tots Motorcycle Parade (Chicago)
- Christkindlmarket Chicago (Chicago)
- A Christmas Carol at Goodman Theatre (Chicago)
- A Christmas Carol at Goodman Theatre (Chicago)
- The Nutcracker by Joffrey Ballet (Chicago)
- The Hip Hop Nutcracker (Chicago)
- One of a Kind Holiday Show (Chicago)
- City of Chicago Christmas Tree Lighting Ceremony (Chicago)
- Rudolph's Rooftop Winter Igloos (Chicago)
🎃 Explore all 10+ featured events below!
Chicago Loop Events Events
The Hip Hop Nutcracker (Chicago) • 0.1 miles
Hip hop dance meets Tchaikovsky's timeless music
Chicagoland Toys for Tots Motorcycle Parade (Chicago) • 0.1 miles
Annual motorcycle parade supporting Toys for Tots
Christkindlmarket Chicago (Chicago) • 0.2 miles
Authentic German-style outdoor holiday market
A Christmas Carol at Goodman Theatre (Chicago) • 0.2 miles
Heartwarming adaptation of a beloved holiday classic.
A Christmas Carol at Goodman Theatre (Chicago) • 0.2 miles
Heartwarming adaptation of a beloved holiday classic.
The Nutcracker by Joffrey Ballet (Chicago) • 0.2 miles
Reimagined Nutcracker set during the 1893 Chicago World's Fair
The Hip Hop Nutcracker (Chicago) • 0.3 miles
Hip hop dance meets Tchaikovsky's timeless music
One of a Kind Holiday Show (Chicago) • 0.3 miles
Chicago's premier holiday shopping destination for unique, handmade gifts.
City of Chicago Christmas Tree Lighting Ceremony (Chicago) • 0.5 miles
Chicago's official Christmas tree lighting ceremony
Rudolph's Rooftop Winter Igloos (Chicago) • 0.5 miles
Cozy heated igloos with panoramic city views
River North Pole (Chicago) • 0.5 miles
St. Jude partnership with festive hotel offerings
Elf in Concert (Chicago) • 0.5 miles
Beloved holiday film with live orchestral score
McCormick Tribune Ice Rink at Millennium Park (Chicago) • 0.6 miles
Iconic urban ice rink with free admission
Millennium Park Holiday Art Market (Chicago) • 0.6 miles
Dozens of local artists showcasing unique crafts
Pinkmas at Museum of Ice Cream Chicago (Chicago) • 0.7 miles
Interactive art installations and unlimited ice cream
Millennium Park Holiday Sing-Along (Chicago) • 0.7 miles
Community carols at Cloud Gate
Maggie Daley Park Skating Ribbon (Chicago) • 0.7 miles
Curving ice ribbon with city skyline views
Jack Frost Christmas Holiday Pop-Up (Chicago) • 0.8 miles
North Pole inspired holiday pop-up experience
Orland Park Fall Bridal Expo (Chicago) • 0.8 miles
Region's largest bridal show with exclusive vendor deals.
Renegade Craft Fair - Chicago Holiday (Chicago) • 1.0 miles
Curated holiday fair featuring 170+ independent artists
Chicago Artisan Market @ Fulton Market (Chicago) • 1.0 miles
Showcasing Midwest's best in food, fashion, home goods, and art.
Holiday Lights Trolley Tour (Chicago) • 1.3 miles
Festive trolley ride through dazzling holiday lights
Navy Pier Winter Fireworks (Chicago) • 1.6 miles
Spectacular winter fireworks display over Lake Michigan
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With 20 years of experience, we use AI technology to build the most comprehensive list of events events.
Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.
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