Southport Avenue is getting dressed up for the season. The Southport Holiday Cocktail Crawl returns to Chicago’s Southport Corridor on Friday, December 4, 2026, from 5:30 to 8:30 p.m.
The neighborhood tradition brings a festive evening of shopping, sipping and strolling to participating stores, restaurants, bars and other businesses along Southport.
Holiday shopping meets a neighborhood celebration
According to the Lakeview Roscoe Village Chamber of Commerce, participating businesses will offer cocktail samples throughout the evening. Holiday carolers will add a soundtrack to the stroll, and guests will have the opportunity to take photos with Santa.
It’s a chance to explore the Corridor after dark, discover local businesses and check off a few holiday gifts while enjoying the neighborhood’s festive atmosphere.
Southport Holiday Cocktail Crawl 2026: Event details
- Date: Friday, December 4, 2026
- Time: 5:30–8:30 p.m.
- Location: Southport Corridor, Chicago
- Activities: Cocktail samples, holiday carolers, photos with Santa and shopping
The participating business list, ticketing details and any restrictions were not specified in the event listing at the time of writing. Check the official Southport Holiday Cocktail Crawl page before heading out.