Chicago on the Cheap

Head to State Street to celebrate Halloween as the “artist’s holiday” with an evening of wonder and creativity at the Arts in the Dark Halloween Parade on October 18, 2025, in the Loop. Recognized as one of the top six Halloween events in the world, the tenth annual Arts in the Dark parade will showcase […]

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Dovetail Brewery and Begyle Brewing serve up their annual fall street festival with Oktoberfestiversary on October 11-12, 2025.  Enjoy brews, live music and food in the Ravenswood neighborhood. Sip on special tappings from Beglye and Dovetail while munching on sausages, lobster rolls and tacos during this annual fest. Live music will kick off at 11:30 […]

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The city’s most anticipated architecture event, the  Chicago Architecture Biennial, unfolds this year with the theme, “SHIFT: Architecture in Times of Radical Change,” featuring exhibits, panel discussions,  films, performances, activations and events across the city through February 28, 2026. The opening weekend kicks off on September 19, 2025. The Biennial opening weekend events take place […]

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Experience the beauty of the fall season with the Chicago River as the backdrop at the Island Party Hut Fall Fest on the Chicago Riverwalk on Saturdays, September 20-October 25, 2025. Enjoy autumn festivities like hay rides on the river, pumpkin patches and eating apple cider donuts along the riverwalk. The Fall Fest will host […]

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Enjoy Fall fun with apple-inspired food, drinks and artisan goods at the Lincoln Square Ravenswood Apple Fest, October 3-5, 2025.  Celebrate the new season with a bounty of edible goodness. Midwest farms will be serving up fresh apples and related dishes and local restaurants and food vendors will offer tasty apple-themed treats. Hard cider, as […]

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