Northwest Side Holiday Trolley Returns to Jefferson Park on December 7, Boosting Local Businesses

By Socialhood News · Il/Chicago/Jefferson Park · November 15, 2025

Jefferson Park shoppers and residents can look forward to a festive way to explore local businesses this holiday season as the Northwest Side Holiday Trolley returns on December 7, 2025. Four trolleys will travel through Jefferson Park, Portage Park, 6 Corners, and Irving-Austin, stopping at participating local businesses where shoppers can take advantage of special deals and sales.

This holiday event comes as Jefferson Park continues to see a resurgence in its business district. The neighborhood is celebrating the return of the Gale Street Inn, a beloved local institution that will reopen in December under new owner Paulo Villabona. A Jefferson Park resident since 2019, Villabona brings 36 years of restaurant industry experience to the iconic eatery. "We fell in love with the neighborhood and the community," said Villabona, who previously worked as general manager of Bar Siena at Old Orchard Mall in Skokie before deciding to revitalize this neighborhood landmark.

Residents interested in participating in the Holiday Trolley event should follow the Jefferson Park Chamber of Commerce social media pages for updates on participating businesses and trolley schedules. The event offers a perfect opportunity to discover local shops while enjoying festive holiday transportation around the Northwest Side neighborhoods.

Sources:
1. https://thechicagogoodlife.com/2024/11/20/chicago-holiday-markets/
2. https://chicago.suntimes.com/restaurants/2025/11/04/jefferson-park-restaurant-gale-street-inn-return-new-owner