Chicago Cinema Weekend Coming in 2027, With Southport’s Music Box Theatre Among Featured Venues
Chicago Cinema Weekend comes March 19–21, 2027, with Southport’s Music Box Theatre among the venues celebrating independent film.
Is Clark Street Becoming Chicago’s Version of Nashville’s Broadway?
From Stolen Saddle and Old Crow to a planned PBR Cowboy Bar and September’s Clark Street Live festival, Wrigleyville’s nightlife strip is finding its country side.
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.
Music Box Theatre’s 43rd Annual Christmas Sing-A-Long Returns to Southport December 5–24
The Music Box Theatre brings its 43rd annual Christmas Sing-A-Long to Southport Avenue December 5–24, 2026, with It's a Wonderful Life, White Christmas, Santa, and holiday carols.
Boystown Halloween Parade 2026: Haunted Halsted Celebrates 30 Years With All-Day Festival
Haunted Halsted turns 30 on October 31, 2026. Here’s the schedule, parade route, family festival details, costume competition, and street closures.
Christkindlmarket Celebrates 30 Years as Wrigleyville Market Returns November 20
Christkindlmarket Wrigleyville returns to Gallagher Way November 20 through December 31, 2026, as the Chicago holiday tradition celebrates 30 years.
Oktoberfest Chicago Returns to Southport Corridor This Weekend
One of the Southport Corridor’s biggest fall traditions is back this weekend as St.
Trick or Treat on Southport Returns October 26 with Candy, Costumes and Halloween Fun
One of the Southport Corridor’s favorite fall traditions is back. Trick or Treat on Southport returns Monday, October 26, from 4 to 7 p.m.
Clark Street Live Bringing New Two-Day Music Festival to Wrigleyville in September
A brand-new street festival is coming to the heart of Wrigleyville this September.
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.