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

Stumblday's hand-checked ranking of the best date night in Pilsen, Chicago, Pilsen, West Town & the West Side the weekend of Sep 25–27, 2026: 1 pick.

1 picks · checked Sep 10

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

More this weekend across Chicago

Chicago Gourmet 2026Harris Theater Rooftop, Downtown, the Loop & West Loop
Chicago Humanities Fall Festival Pilsen Day 2026National Museum of Mexican Art, Pilsen, West Town & the West Side
13th Annual Beverly Art WalkWestern Avenue in Beverly/Morgan Park, Hyde Park, Bronzeville & the South Side
Hyde Park Jazz Festival 2026Multiple Hyde Park venues, Hyde Park, Bronzeville & the South Side
World Music Festival Chicago 2026Multiple Chicago venues
Fall Fest at Lincoln Park ZooLincoln Park Zoo, Lincoln Park, Lakeview & Wrigleyville