Cheap Flights from Chicago to Cancun from

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Roundtrip flights from Chicago to Punta Ca... starting at $288

Roundtrip flights from Chicago to Cancun starting at $266

Roundtrip flights from Chicago to Las Vega... starting at $129

Roundtrip flights from Chicago to Montego... starting at $389

Roundtrip flights from Chicago to Los Ange... starting at $113

Roundtrip flights from Chicago to Tokyo starting at $569

Roundtrip flights from Chicago to Orlando starting at $127

Roundtrip flights from Chicago to London starting at $352

Roundtrip flights from Chicago to Mexico C... starting at $278

Roundtrip flights from Chicago to San Juan starting at $304