Flight deals from Chicago - Book cheap flights

February 10, 2021

Chicago to the Dominican Republic for only $251 roundtrip (Apr-May dates)

Cheap flights from Chicago to the Dominican Republic for only $251 roundtrip with United Airlines.

January 30, 2021

Chicago or Cleveland to the Dominican Republic from only $252 roundtrip (Mar-May dates)

Cheap flights from Chicago or Cleveland to the Dominican Republic from only $252 roundtrip with United Airlines.

January 1, 2021

Chicago to San Andres Island, Colombia for only $239 roundtrip (Mar-May dates)

Cheap flights from Chicago to San Andres Island, Colombia for only $239 roundtrip with Copa Airlines.

December 31, 2020

⚠️ ERROR FARE ⚠️ SUMMER: Many US cities to Africa from only $262 roundtrip (Mar-Sep dates)

Error Fare, summer flights from Many US cities to Africa from only $262 roundtrip with TAP Air Portugal.

December 29, 2020

New York or Chicago to Rio de Janeiro, Brazil from only $329 roundtrip (Feb-May dates)

Cheap flights from New York or Chicago to Rio de Janeiro, Brazil from only $329 roundtrip with Copa Airlines.

December 28, 2020

New York or Chicago to Dubai, UAE for only $542 roundtrip (Feb-May dates)

Cheap flights from New York or Chicago to Dubai, UAE for only $542 roundtrip with Etihad Airways.

December 24, 2020

🔥 Non-stop from Chicago to San Jose, California (& vice versa) for only $89 roundtrip (Mar-May dates)

Non-stop flights from Chicago to San Jose, California for only $89 roundtrip with American Airlines. Also works in reverse.

December 14, 2020

🔥 Chicago to Lima, Peru for only $261 roundtrip (Feb-Apr dates)

Cheap flights from Chicago to Lima, Peru for only $261 roundtrip with Aeromexico.

December 8, 2020

SUMMER: Chicago to Buenos Aires, Argentina for only $460 roundtrip (Mar-Sep dates)

Summer flights from Chicago to Buenos Aires, Argentina for only $460 roundtrip with Copa Airlines.