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Chicago Festivals 2025 Calendar Ailis Halimeda. Explore all the happening events in Chicago in 2025 with us that best suit your interest 6 - 16, 2025) 70th annual Chicago River dyeing (March 15, 2025) 55th annual Chicago Pride Parade (June 29, 2025) NASCAR Chicago Street Race Weekend (July 5 - 6, 2025) 40th annual Chicago Jazz Festival (August/September 2025) 65th annual Chicago Air & Water Show (August 2025) 45th annual Taste of Chicago (September.

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