Flight deals from Chicago - Book cheap flights

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Chicago to Colombo, Sri Lanka for only $657 roundtrip

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Feb 3, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Sao Paulo, Brazil for only $440 roundtrip

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Jan 31, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Gothenburg, Sweden for only $360 roundtrip

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Jan 28, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from Chicago to Cancun, Mexico for only $290 roundtrip

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Jan 27, 2026 FLIGHT DETAILS & AIRLINE

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Non-stop from 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