Holiday Magic Awaits in Wicker Park Bucktown
Bring the whole family for a day of festive fun and adventure!
Capture the moment with free photos with Santa and cozy up by the fire with gooey s’mores.
Ride in style on the Holiday Rickshaws and the WPB Shopping Shuttle to enchanting stops like the North Pole and Whoville.
Join the excitement with your Wonderland Map and take part in the Holiday Grinch Hunt—spot the sneaky Grinch for a chance to win a WPB shopping spree!
Parents, finish your holiday shopping while supporting local shops offering exclusive in-store deals all along WPB’s shopping corridors.
Don’t miss the grand finale—the Wicker Park Holiday Tree Lighting, proudly presented by WPB SSA #33.
It’s a day of holiday magic, delicious treats, and joyful community spirit!
Shop Small. Support Local. Celebrate Together.
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. The deadline for the complimentary listing is November 25.
Sponsor Winter Wonderland. Check out the newest level:
Premium Member Logo Inclusion of $100
Your logo will be prominently displayed on the printed event map for the Premium Member Logo Inclusion sponsorship, ensuring maximum visibility. The map will be available at participating retailers throughout the WPB neighborhood, guaranteeing exposure. As well as distributed at the SSA #33 Wicker Park Tree Lighting leading into Winter Wonderland. *This sponsorship level is exclusively for members with brick-and-mortar businesses. Deadline for the Premium logo placement is November 14 , 2025
*Please note: the holiday shopping map will go live November 26 in time for the Thanksgiving shopping weekend and will be available on the Chamber website, social media and holiday marketing through December 31, 2026