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Things to do in Chicago in January 2027 – page 5

166 upcoming events. Chicago, IL, United States.

Updated October 30, 2026 · January 2027 listings

166 upcoming events

Broadway In Chicago
Jan27Wed
Plays & Musicals

All Things Equal

Wed, Jan 27 · 7:00 PM

Broadway Playhouse at Water Tower Place

Alex Falcone
Jan28Thu
Comedy

Alex Falcone

Jan 28, 29, and 30, 2027

Zanies Comedy Club

Broadway In Chicago
Jan28Thu
Plays & Musicals

All Things Equal

Thu, Jan 28 · 7:00 PM

Broadway Playhouse at Water Tower Place

Colin Hay
Jan28Thu
Concerts

Colin Hay

Thu, Jan 28 · 8:00 PM

Old Town School of Folk Music

Chicago Shakespeare Theater
Jan29Fri
Plays & Musicals

Romeo Y Julieta

Fri, Jan 29 · 7:00 PM

Chicago Shakespeare Theater

Colin Hay
Jan29Fri
Concerts

Colin Hay

Fri, Jan 29 · 8:00 PM

Gary and Laura Maurer Concert Hall

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