Old Town Theater District

Old Town Theater District in Chicago

Since the 1950s, the Old Town neighborhood has been a center for culture and counterculture. From this came a focus on arts and entertainment in the community. Today, Old Town is home to three theaters: A Red Orchid Theatre, The Second City, and Zanies Comedy Club. Each bring its own style of theater and offer Chicago many ways to enjoy the arts.

A Red Orchid Theatre
1531 N Wells Street
(312) 943-8722

In 1993, Michael Shannon, Guy Van Swearingen IV and Lawrence Grimm founded A Red Orchid Theatre, offering powerful and intimate productions by their ensemble of actors. Their ensemble of dedicated artists presents new plays from around the world and revives insightful past works that offer new insight in today’s world.

Their 2019-2020 season will consist of the world premiere of “Grey House” by ensemble member Levi Holloway, the Chicago premiere of “Do You Feel Anger” by Mara Nelson-Greenberg, and the Chicago premiere of “The Moors” by Jen Silverman.

The Second City
1616 N Wells Street
(312) 337-3992

The Second City opened its doors in 1959, ushering in a new era of comedy. Co-founded by Bernie Sahlins, Howard Alk, and Paul Sills, The Second City has became a worldwide comedy empire. The Second City has entertained audiences with live shows featuring Chicago-influenced sketch and improve comedy, and has trained comics on how to develop their voice. Alumni of their programs, like Tina Fey, Bill Murray and Stephen Colbert, have gone on to perform on Saturday Night Live and have illustrious comedy careers.

Zanies Comedy Club
1548 N Wells Street
(312) 337-4027

In 1978, Rick Uchwat opened Zanies Comedy Club in Chicago and today it’s the city’s longest-running comedy club, and fourth-oldest in the nation, with national touring headliners every night. It is known for unique standup in an intimate venue. Stars like Lewis Black, Chris Rock, Dave Chappelle and Kevin Hart have all performed at Zanies.