4 Chicago Restaurants and Bars That Take Dinner and a Show to the Next Level

Elaine Glusak | April 21, 2020 | Food & Drink

When it comes to Chicago’s ever-innovating food and drink scene, it’s no longer enough to just serve wildly creative cocktails and ’grammable foodie delights. Now it’s all about entertainment, from cabaret acts and drag queen performances to jugglers and aerialists dangling over your dinner plate.


Teatro ZinZanni
“A restaurant is a terrific environment for any theatrical show because the audience is relaxed,” says Norman Langill, founder and creative director of the adult circus dinner theater. Above the tables in an opulent, mirror-ringed spiegeltent, a pair of aerialists intertwine and a contortionist swings on a hoop. Between them, buoyant ballads and risqué banter segue into clowning acts and improv sketches. Throughout, the audience dines on four courses from chef Debbie Sharpe, ranging from braised short ribs to cheesecake with salted caramel popcorn. “Dinner and circus blend like a great party,” Langill says. 32 W. Randolph St.

The Darling
The West Loop speakeasy conjures its own sultry party vibe with engaging performers whose skills range from burlesque to drag Rihanna to musically choreographed contortion and torch singing. They command your attention between craft cocktails—quaff the rum-based Darling Buds of May, atop which is printed a flower bouquet—roughly once an hour. 905 W. Randolph St.

The Drifter
Drinks plus diversions means “people on a first date who don’t know what to say to each other will put their phones down and have something to talk about,” says Jill Anderson, bar manager of this Prohibition-era subterranean speakeasy. The 37-seater may lift its red curtain on a Led Zeppelin burlesque dance or a banjo band (all acts curated by burlesque legend Michelle L’amour) opposite the period bar and antique circus banners. 676 N. Orleans St.

Encouraging patrons to tuck tips into their cleavage, performers at the near South Side spot occupy the extremist end of audience interactivity, offering over-the-top lip-syncing, full dinners and boozy shots. “The more you drink,” says a cast member playing Glenda from Wicked on Broadway night, “the prettier we look.” 2229 S. Michigan Ave.

Tags: dining

Photography by: courtesy of Teatro ZinZanni