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Date night in Evanston, Chicago the Weekend of Sep 25–27, 2026

Stumblday's hand-checked ranking of the best date night in Evanston, Chicago, Evanston & Oak Park the weekend of Sep 25–27, 2026: 5 picks.

5 picks · checked Sep 21

WhenAll weekendFri nightSaturdaySat nightSundaySun night
WhereAll ChicagoDowntown, the Loop & West LoopLincoln Park, Lakeview & WrigleyvilleLogan Square, Wicker Park & BucktownPilsen, West Town & the West SideHyde Park, Bronzeville & the South SideAndersonville, Uptown & Lincoln SquareEvanston & Oak ParkFar Suburbs
WhatAllFreeArtMusicMarketsOutdoorsFoodDate night

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More this weekend across Chicago

Hyde Park Jazz Festival 2026Multiple Hyde Park venues, Hyde Park, Bronzeville & the South Side
Teddy Swims – The Ugly TourUnited Center, 1901 W Madison, Pilsen, West Town & the West Side
2026 Presidents CupMedinah Country Club (Course No. 3), Medinah, Far Suburbs
Sara Bareilles – Good Grief TourThe Chicago Theatre, Downtown, the Loop & West Loop
Foster The People – Good Mourning Sunshine TourHuntington Bank Pavilion at Northerly Island, 1300 S. Linn White Drive, Downtown, the Loop & West Loop
Chicago Gourmet 2026Harris Theater Rooftop, Downtown, the Loop & West Loop