Flight deals from Chicago - Book cheap flights

August 11, 2025

Chicago to Jakarta, Indonesia for only $613 roundtrip

Cheap flights from Chicago to Jakarta, Indonesia for only $613 roundtrip with Cathay Pacific.

August 7, 2025

Chicago to Taipei, Taiwan for only $659 roundtrip

Cheap flights from Chicago to Taipei, Taiwan for only $659 roundtrip with Cathay Pacific.

August 4, 2025

Chicago to Auckland, New Zealand for only $736 roundtrip

Cheap flights from Chicago to Auckland, New Zealand for only $736 roundtrip with Air Canada.

July 10, 2025

US cities to Madrid, Spain from only $273 roundtrip

Cheap flights from US cities to Madrid, Spain from only $273 roundtrip with TAP Air Portugal.

July 9, 2025

US cities to Spanish cities from only $328 roundtrip

Cheap flights from US cities to Spanish cities from only $328 roundtrip with TAP Air Portugal.

July 8, 2025

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

Cheap flights from US cities to Rome or Milan, Italy from only $314 roundtrip with TAP Air Portugal.

July 6, 2025

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

Summer flights from Chicago to Tulum, Mexico for only $282 roundtrip with United Airlines.

July 4, 2025

Chicago to Zurich, Switzerland for only $374 roundtrip

Cheap flights from Chicago to Zurich, Switzerland for only $374 roundtrip with Scandinavian Airlines.

June 25, 2025

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

Non-stop, summer flights from Chicago to Guatemala City, Guatemala for only $78 one-way with United Airlines.