Flight deals from Chicago - Book cheap flights

MONTHS

SUMMER: US cities to Calgary, Canada from only $161 roundtrip

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Feb 25, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Austin, Texas (& vice versa) for only $115 roundtrip

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Feb 22, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Orlando, Florida (& vice versa) for only $95 roundtrip

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Feb 22, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Charlotte, North Carolina to Chicago (& vice versa) for only $103 roundtrip

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Feb 22, 2026 FLIGHT DETAILS & AIRLINE

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US cities to Dubai, UAE from only $615 roundtrip

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Feb 20, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Maputo, Mozambique for only $596 roundtrip

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Feb 18, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Tampa, Florida (& vice versa) for only $157 roundtrip

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Feb 16, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Nashville (& vice versa) for only $115 roundtrip

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Feb 15, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Philadelphia (& vice versa) for only $103 roundtrip

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Feb 15, 2026 FLIGHT DETAILS & AIRLINE