Stumblday's hand-checked ranking of the best free things to do in Oak Park, Chicago, Evanston & Oak Park the weekend of Sep 25–27, 2026: 5 picks.
5 picks · checked Sep 21
Downtown Oak Park, Oak Park, Evanston & Oak ParkA free downtown Oak Park street festival with live music, local food and craft beer.
Downtown Oak Park, Oak Park, Evanston & Oak ParkA free downtown Oak Park street festival with live music, local food and craft beer.
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Downtown Glenview (Church Street and Pine Street stages), Glenview, Evanston & Oak ParkLos Lobos headlines a free downtown Glenview block party with two stages.
Downtown Glenview (Church Street and Pine Street stages), Glenview, Evanston & Oak ParkLos Lobos headlines a free downtown Glenview block party with two stages.
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Parkway Bank Park, Rosemont, Evanston & Oak ParkRosetober Fest brings German music, dance, contests and live carving to Parkway Bank Park.
Parkway Bank Park, Rosemont, Evanston & Oak ParkRosetober Fest brings German music, dance, contests and live carving to Parkway Bank Park.
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Block Museum of Art, Evanston & Oak ParkPicturing the Modern Metropolis: Prints and Photographs has enough weekend energy to earn a spot on the board.
Block Museum of Art, Evanston & Oak ParkPicturing the Modern Metropolis: Prints and Photographs has enough weekend energy to earn a spot on the board.
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Block Museum of Art, Evanston & Oak ParkThe Block Collects 2026 has enough weekend energy to earn a spot on the board.
Block Museum of Art, Evanston & Oak ParkThe Block Collects 2026 has enough weekend energy to earn a spot on the board.
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