November is packed with things to do across Chicago.

Insider773 is teaming up with TBOX Bar Crawls to give Chicago residents a chance to win six tickets to the 30th Anniversary Twelve Bars of Xmas Crawl , taking place Saturday, December 12, in Wrigleyville.

CHICAGO — Light, music and architectural projections come together at Celestia, a seated immersive experience at St. Vincent de Paul Catholic Church, 1010 W. Webster Ave. in Lincoln Park. Tickets are available online.

Halloween season is officially here, Chicago.

420 Frankenstein is bringing a cannabis-infused take on Mary Shelley’s classic story to Chicago this fall. The comedy show puts a new spin on Frankenstein, combining live theater, improvisation and cannabis for a different experience each night.

WIGS is bringing a unique twist to stand-up comedy in Chicago, with local comedians performing their sets while wearing wigs. The concept puts a playful spin on traditional stand-up, giving comedians the opportunity to take on different looks and personas. The show is hosted by Chicago comedian Ron Hexagon and Claire Parlette .

Chicago, IL — The Windy City Comedy Fest will return to Chicago from August 6–9, 2026 , bringing more than 50 comedians to venues across the city for four days of stand-up performances, showcases, and events celebrating Chicago’s thriving comedy community.

After building a reputation for blending alternative comedy, spirited competition, and cannabis culture into one uniquely interactive experience, HighQ: America’s Favorite Drug Test is launching a new weekly comedy & variety showcase in Chicago: HighQ Hangout.

CHICAGO — Insider773 is bringing together wine lovers and house music fans this summer with the debut of " Catch a Vine ," a wine and house music pop-up taking place on Saturday , July 11 , at VIN312 Winery in Chicago's Ravenswood neighborhood.