Flight deals from Chicago - Book cheap flights

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US cities to Lisbon, Portugal from only $386 roundtrip

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Jan 22, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Dubai, UAE for only $561 roundtrip

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Jan 21, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to German cities from only $184 one-way

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Jan 19, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to French cities from only $186 one-way

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Jan 18, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Dublin, Ireland for only $359 roundtrip

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Jan 16, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Cancun, Mexico for only $281 roundtrip

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Jan 12, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Seattle (& vice versa) for only $133 roundtrip

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Jan 6, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Oslo, Norway for only $377 roundtrip

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Jan 4, 2026 FLIGHT DETAILS & AIRLINE

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US cities to Toronto, Canada from only $179 roundtrip

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Dec 16, 2025 FLIGHT DETAILS & AIRLINE