Flight deals from Chicago - Book cheap flights

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.

December 3, 2020

XMAS & NEW YEAR: Business Class from Chicago to Rio de Janeiro, Brazil for only $900 roundtrip (Dec-Jan dates) (lie-flat seats)

Business Class, Christmas and New Year flights from Chicago to Rio de Janeiro, Brazil for only $900 roundtrip with United Airlines.

November 17, 2020

Chicago to Oaxaca, Mexico for only $296 roundtrip (Apr-Jun dates)

Cheap flights from Chicago to Oaxaca, Mexico for only $296 roundtrip with American Airlines.

November 12, 2020

🔥 SUMMER: US cities to South America from only $200 roundtrip

Summer flights from US cities to South America from only $200 roundtrip with Delta Air Lines.

November 11, 2020

SUMMER: Chicago to Santiago, Chile for only $401 roundtrip (Jan-Sep dates)

Summer flights from Chicago to Santiago, Chile for only $401 roundtrip with Copa Airlines.

November 3, 2020

SUMMER: Chicago to Havana, Cuba for only $205 roundtrip (Jun-Sep dates)

Summer flights from Chicago to Havana, Cuba for only $205 roundtrip with Copa Airlines.

October 27, 2020

Chicago to Trinidad for only $255 roundtrip (Jan dates)

Cheap flights from Chicago to Trinidad for only $255 roundtrip with JetBlue.

October 18, 2020

Chicago or Houston to Nairobi, Kenya from only $591 roundtrip (Jan-May dates)

Cheap flights from Chicago or Houston to Nairobi, Kenya from only $591 roundtrip with Turkish Airlines.

October 10, 2020

Chicago to Manchester, UK for only $385 roundtrip (Apr dates)

Cheap flights from Chicago to Manchester, UK for only $385 roundtrip with TAP Air Portugal.