Ravenswood Celebrates Local Excellence with 2025 Best of Business Awards as Holly Jolly Trolley Returns for Holiday Shopping Season

By Socialhood News · Il/Chicago/Ravenswood · November 24, 2025

The Greater Ravenswood Chamber of Commerce recently announced the winners of their highly anticipated 2025 Best of Ravenswood Awards, recognizing outstanding local businesses that exemplify the neighborhood's unique character and commitment to community.

The annual awards celebrate the diverse array of businesses that make Ravenswood one of Chicago's most vibrant commercial districts. This recognition arrives just in time for the holiday shopping season, as residents prepare for the return of the popular Holly Jolly Trolley on Saturday, November 29th. The free trolley service will operate from 11:00 AM to 5:00 PM, making multiple stops throughout the neighborhood and connecting shoppers to hundreds of local small businesses without parking concerns. This beloved community service allows residents and visitors to easily discover exciting shopping offers while supporting local entrepreneurs during the crucial holiday retail period.

Residents looking to support these award-winning businesses can also participate in the Unwrap Ravenswood Holiday Rewards program, where shoppers spending $300 at a minimum of three qualifying local businesses can receive $75 in gift cards to Ravenswood stores and restaurants. The Chamber encourages neighbors to celebrate local excellence by visiting these recognized establishments throughout the holiday season.

Sources:
1. https://ravenswoodchicago.org/
2. https://ravenswoodchicago.org/neighborhood/