Best Of

Best Shows in Chicago, Illinois

A city-level look at the strongest upcoming shows inventory in Chicago.

534 upcoming eventsChicago, IL

The Second City Mainstage 114th Revue

📅Fri, Oct 16, 2026, 2:00 PM•Chicago, IL

Second City Chicago - Mainstage

Waitress

📅Fri, Oct 16, 2026, 2:00 PM•Chicago, IL

Nederlander Theatre Chicago

Jekyll and Hyde - The Musical

📅Fri, Oct 16, 2026, 2:00 PM•Chicago, IL

Broadway Playhouse at Water Tower Place

Drunk Shakespeare - Drunk Dracula

📅Fri, Oct 16, 2026, 2:00 PM•Chicago, IL

The Lion Theatre

Brad Williams

📅Fri, Oct 16, 2026, 2:30 PM•Chicago, IL

Chicago Theatre

Drunk Shakespeare - Drunk Dracula

📅Fri, Oct 16, 2026, 4:00 PM•Chicago, IL

The Lion Theatre

The Second City Mainstage 114th Revue

📅Fri, Oct 16, 2026, 5:00 PM•Chicago, IL

Second City Chicago - Mainstage

Waitress

📅Sat, Oct 17, 2026, 9:00 AM•Chicago, IL

Nederlander Theatre Chicago

Jekyll and Hyde - The Musical

📅Sat, Oct 17, 2026, 9:00 AM•Chicago, IL

Broadway Playhouse at Water Tower Place

Drunk Shakespeare - Drunk Dracula

📅Sat, Oct 17, 2026, 10:00 AM•Chicago, IL

The Lion Theatre

Drunk Shakespeare - Drunk Dracula

📅Sat, Oct 17, 2026, 12:00 PM•Chicago, IL

The Lion Theatre

The Second City Mainstage 114th Revue

📅Sat, Oct 17, 2026, 2:00 PM•Chicago, IL

Second City Chicago - Mainstage

Drunk Shakespeare - Drunk Dracula

📅Sat, Oct 17, 2026, 2:00 PM•Chicago, IL

The Lion Theatre

Waitress

📅Sat, Oct 17, 2026, 2:30 PM•Chicago, IL

Nederlander Theatre Chicago

Jekyll and Hyde - The Musical

📅Sat, Oct 17, 2026, 2:30 PM•Chicago, IL

Broadway Playhouse at Water Tower Place

Drunk Shakespeare - Drunk Dracula

📅Sat, Oct 17, 2026, 4:00 PM•Chicago, IL

The Lion Theatre

The Second City Mainstage 114th Revue

📅Sat, Oct 17, 2026, 5:00 PM•Chicago, IL

Second City Chicago - Mainstage

Jekyll and Hyde - The Musical

📅Sun, Oct 18, 2026, 8:00 AM•Chicago, IL

Broadway Playhouse at Water Tower Place

Waitress

📅Sun, Oct 18, 2026, 9:00 AM•Chicago, IL

Nederlander Theatre Chicago

Drunk Shakespeare - Drunk Dracula

📅Sun, Oct 18, 2026, 12:00 PM•Chicago, IL

The Lion Theatre

In Conversation with Joe Dombrowski

📅Sun, Oct 18, 2026, 1:00 PM•Chicago, IL

The Den Theatre

The Second City Mainstage 114th Revue

📅Sun, Oct 18, 2026, 2:00 PM•Chicago, IL

Second City Chicago - Mainstage

Drunk Shakespeare - Drunk Dracula

📅Sun, Oct 18, 2026, 2:00 PM•Chicago, IL

The Lion Theatre

Drunk Shakespeare - Drunk Dracula

📅Mon, Oct 19, 2026, 2:00 PM•Chicago, IL

The Lion Theatre