Stumblday's hand-checked ranking of the best date night in Old Town, Chicago, Lincoln Park, Lakeview & Wrigleyville the weekend of Sep 25–27, 2026: 3 picks.
3 picks · checked Sep 21
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopTim Convy & Sean O'Brien at Zanies Chicago has enough weekend energy to earn a spot on the board.
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopTim Convy & Sean O'Brien at Zanies Chicago has enough weekend energy to earn a spot on the board.
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Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopCliff Cash at Zanies Chicago has enough weekend energy to earn a spot on the board.
Zanies Comedy Night Club, Old Town, Downtown, the Loop & West LoopCliff Cash at Zanies Chicago has enough weekend energy to earn a spot on the board.
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A Red Orchid Theatre, Old Town, Lincoln Park, Lakeview & WrigleyvilleJohn Judd and Cassidy Slaughter-Mason return in the four-Jeff-Award production for a limited run.
A Red Orchid Theatre, Old Town, Lincoln Park, Lakeview & WrigleyvilleJohn Judd and Cassidy Slaughter-Mason return in the four-Jeff-Award production for a limited run.
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