Flight deals from Chicago - Book cheap flights

MONTHS

Chicago to Reykjavik, Iceland for only $368 roundtrip

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Jul 15, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Chicago to Denver, Colorado (& vice versa) for only $159 roundtrip

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Jul 9, 2026 FLIGHT DETAILS & AIRLINE

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US cities to Stockholm, Sweden from only $357 roundtrip

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Jul 8, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Chicago to Phoenix, Arizona (& vice versa) for only $177 roundtrip

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Jul 8, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: New York to Chicago (& vice versa) for only $128 roundtrip

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Jul 7, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Boston to Chicago (& vice versa) for only $149 roundtrip

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Jul 5, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to St. Martin for only $316 roundtrip

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Jul 3, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Chicago to the Bahamas for only $322 roundtrip

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Jul 1, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Liberia, Costa Rica for only $300 roundtrip

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Jun 30, 2026 FLIGHT DETAILS & AIRLINE