Chicago Bears
The Holiday Specials
Winter Olympics 2026
Charity Rides
Local Engagement
360 Degree Art
Monsters of the Midway 2025/ 2026 ride of a lifetime. Highlights included Cheese Grater interview with NBC's Matt in the Morning, in Sidecar interview with Bears' Lauren Screeden, Viral 400K view in Instagram collab with Chicago Ball Hawk, Tailgate Rides and a live experience in Soldier Field for the NFC Divisional Playoff game
A ten-year venture in urban cheer, The Holiday Ride brings the spirit of the season to the streets. Our decade-long trek across the city has featured a rotating cast of festive icons—including Hanukkah Harry, a live three-piece band, and even the Abominable Snow Monster—creating a mobile holiday spectacle unlike any other.
The 2026 Winter Olympics brought the world to Cortina, but Windy City Sidecar brought the soul of Italy to the streets of Chicago. Featuring the iconic Vespa PX 150, our experience was a masterclass in synergy—blending Olympic prestige with a timeless, vintage amore.
Lane Tech High School made state for only the second time ever in the 2025/ 2026 season. This activation brought school pride to a whole different level by showcasing the Yeti in old school Lane gear for their send off from the home Alley, Diversy River Bowl.
