Top Chicago Comedy Shows

Step inside landmark building of Harry Caray's Italian Steakhouse in River North, once owned by infamous Chicago mobster Frank Nitti, and travel back in time for dinner and a show based on the real-life murder of Eddie O'Hare. This irreverent comedy features an ensemble cast of characters, many of whom walked the very halls of 33 W. Kinzie back when Nitti called it home. The immersive experience invites you to step into the role of partygoer at Frank Nitti's birthday, and delve into the unsolved murder of Edward J. "Easy Eddie" O'Hare -- Al Capone's lawyer and father of war hero Butch O'Hare for whom the airport is named. The crime was never solved, but suspects included Frank Nitti, his wife Annette, Al Capone and several others. Can you crack the case? The interactive show is filled with historical anecdotes, laughs, audience interaction and toe-tapping musical productions.

Enjoy a one-of-a-kind night at the theatre when you attend Chicago’s irreverent and comedic “Drunk Shakespeare” performance. Pick between two different start times, and choose a seating area that suits your budget and preferences. Then, sit back, relax, and prepare to laugh as an actor downs five shots of whiskey before attempting to perform in one of Shakespeare’s plays.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.