Flight deals from Chicago - Book cheap flights

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Non-stop from Chicago to Toronto, Canada for only $167 roundtrip

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Nov 24, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Cali, Colombia for only $283 roundtrip

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Nov 21, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Rio de Janeiro, Brazil for only $424 roundtrip

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Nov 3, 2025 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Reykjavik, Iceland for only $375 roundtrip

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Nov 1, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Sydney, Australia for only $770 roundtrip

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Oct 31, 2025 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to the US Virgin Islands for only $242 roundtrip

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Oct 29, 2025 FLIGHT DETAILS & AIRLINE

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US cities to Manila, Philippines from only $498 roundtrip

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Oct 28, 2025 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to San Juan, Puerto Rico for only $218 roundtrip

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Oct 26, 2025 FLIGHT DETAILS & AIRLINE

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Non-stop from Baltimore to Chicago (& vice versa) for only $139 roundtrip

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Oct 25, 2025 FLIGHT DETAILS & AIRLINE