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Date night in Rosemont, Chicago the Weekend of Oct 2–4, 2026

Stumblday's hand-checked ranking of the best date night in Rosemont, Chicago, Evanston & Oak Park the weekend of Oct 2–4, 2026: 1 pick, refreshed weekly.

1 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

Planning ahead for Oct 2–4, 2026?

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More this weekend across Chicago

Chicago Bears vs. New York JetsSoldier Field, Downtown, the Loop & West Loop
Doja Cat – Tour Ma Vie World TourUnited Center, Pilsen, West Town & the West Side
LE Sserafim – Pureflow TourUnited Center, Pilsen, West Town & the West Side
Bill Burr LiveThe Chicago Theatre, 175 N State St, Downtown, the Loop & West Loop
Lincoln Square Ravenswood Apple Fest 2026Lincoln Avenue, Lawrence to Sunnyside, Lincoln Square, Andersonville, Uptown & Lincoln Square
The Chicks: Taking the Long WayThe Auditorium, 50 E Ida B. Wells Drive, Downtown, the Loop & West Loop