Flight deals from Chicago - Book cheap flights

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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

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Chicago to Guayaquil, Ecuador for only $394 roundtrip

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Jun 26, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Non-stop from Chicago to the Dominican Republic for only $335 roundtrip

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Jun 18, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: US cities to the Bahamas for only $284 roundtrip

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May 26, 2026 FLIGHT DETAILS & AIRLINE

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🔥 Non-stop from Chicago to San Juan, Puerto Rico for only $44 one-way

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May 6, 2026 FLIGHT DETAILS & AIRLINE

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Chicago to Delhi, India for only $562 roundtrip

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Apr 23, 2026 FLIGHT DETAILS & AIRLINE

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SUMMER: Non-stop from Chicago to Portland, Oregon (& vice versa) for only $195 roundtrip

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Apr 21, 2026 FLIGHT DETAILS & AIRLINE