Flight deals from Chicago - Book cheap flights

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US cities to Rome or Milan, Italy from only $314 roundtrip

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Jul 8, 2025 FLIGHT DETAILS & AIRLINE

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SUMMER: Chicago to Tulum, Mexico for only $282 roundtrip

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Jul 6, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Zurich, Switzerland for only $374 roundtrip

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Jul 4, 2025 FLIGHT DETAILS & AIRLINE

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🔥 SUMMER: Chicago to Guatemala City, Guatemala for only $78 one-way

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Jun 25, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to Geneva, Switzerland for only $362 roundtrip

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Jun 15, 2025 FLIGHT DETAILS & AIRLINE

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SUMMER: US cities to Colombian cities from only $221 roundtrip

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Jun 15, 2025 FLIGHT DETAILS & AIRLINE

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SUMMER: Chicago to the Dominican Republic for only $265 roundtrip

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May 27, 2025 FLIGHT DETAILS & AIRLINE

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US cities to Brussels, Belgium from only $297 roundtrip

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May 22, 2025 FLIGHT DETAILS & AIRLINE

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Chicago to European cities from only $374 roundtrip

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May 20, 2025 FLIGHT DETAILS & AIRLINE