Roscoe Village Winterfest Returns December 5–6, 2026
Roscoe Village Winterfest returns December 5–6, 2026, with a weekend focused on neighborhood holiday traditions, family activities and local shopping.
Southport Holiday Cocktail Crawl Returns December 4, 2026
Sip, shop and celebrate on Southport Avenue Friday, December 4, 2026, as the Southport Holiday Cocktail Crawl returns with samples, carolers and Santa.
Lakeview Tree Lighting Returns November 22, 2026, at Lincoln and Wellington
Lakeview's 2026 holiday tree lighting takes place November 22 at Lincoln and Wellington, with carolers, goody bags and a special North Pole visitor.
Christkindlmarket Wrigleyville Returns To Gallagher Way Nov. 20
Holiday season at Wrigley Field is officially on the calendar. Christkindlmarket Wrigleyville will return to Gallagher Way on Friday, Nov.