Flight deals from Chicago - Book cheap flights

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Chicago to Santa Cruz, Bolivia for only $446 roundtrip

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Sep 9, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Amman, Jordan for only $677 roundtrip

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Sep 9, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Edmonton, Canada for only $157 roundtrip

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Sep 7, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Manaus, Brazil for only $402 roundtrip

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Sep 4, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Rome, Italy for only $375 roundtrip

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Sep 4, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to European cities from only $356 roundtrip

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Aug 28, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to South American cities from only $290 roundtrip

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Aug 27, 2025 FLIGHT DETAILS & AIRLINE

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US cities to Kaohsiung, Taiwan from only $520 roundtrip

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Aug 24, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Vancouver, Canada for only $124 roundtrip

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Aug 20, 2025 FLIGHT DETAILS & AIRLINE