Get ready for a day of holiday magic in Wicker Park Bucktown! Join us for our annual WPB Winter Wonderland & Tree Lighting, a festive, family-friendly celebration filled with holiday cheer, neighborhood shopping, delicious treats, and activities for all ages!
Explore the neighborhood, shop local businesses, and enjoy a variety of FREE holiday activities, including:
- Free Photos with Santa
- Fireside S’mores
- Holiday Rickshaws throughout WPB
- Holiday Gnome Hunt
- Visits from the Grinch
- Holiday Music & Carolers
- Wicker Park Holiday Tree Lighting, proudly presented by WPB SSA #33
- NEW THIS YEAR: Ice Skating Comes to WPB!
We're bringing even more holiday magic to the neighborhood with FREE ice skating! Lace up your skates and enjoy this exciting new winter experience right in the heart of Wicker Park Bucktown.
Whether you're shopping for the perfect holiday gifts, enjoying seasonal treats, or making memories with family and friends, Winter Wonderland is the perfect way to celebrate the season while supporting the local businesses that make our neighborhood special.
Mark your calendars, bundle up, and join us for a magical day in Wicker Park Bucktown!
Shop Small. Support Local. Celebrate Together.
WPB Winter Wonderland & Tree Lighting is brought to you by the Wicker Park Bucktown Chamber of Commerce, SSA #33, the Wicker Park Advisory Board, Chicago Park District and Indie Row Bucktown.
How can you participate?
Register the complimentary listing in the holiday digital shopping map. The map will be available beginning Small Business Saturday weekend, so it's crucial to register early to be included in all SBS and Winter Wonderland marketing efforts. Note: A digital map QR code will be featured on the Winter Wonderland printed map, billboards and all marketing materials.
Premium Member Logo Inclusion – Only $100!
Looking for an affordable way to get your business in front of holiday shoppers this season? We've added a sponsorship opportunity exclusively for our brick-and-mortar Chamber members!
For just $100, your business logo will be featured on the official Winter Wonderland & Tree Lighting PRINTED event map, putting your business front and center as thousands of neighbors and visitors shop, explore, and celebrate the holidays in Wicker Park Bucktown.
The maps will be distributed before the event throughout the neighborhood before and during the event.
It's a simple, budget-friendly way to boost your visibility, support a beloved neighborhood tradition, and remind shoppers to shop small and support local!
Don't miss out! The deadline to secure your logo placement is Wednesday, November 4, 2026. Purchase your logo inclusions here.
This exclusive sponsorship opportunity is available to WPBCC members with brick-and-mortar locations only.
Secure Your Spot Today!
*Please note: the holiday shopping map will go live November 25 in time for the Thanksgiving shopping weekend and will be available on the Chamber website, social media and holiday marketing through December 31, 2026