Flight deals from Chicago - Book cheap flights

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.

June 23, 2025

Non-stop from US cities to Reykjavik, Iceland from only $300 roundtrip

Non-stop flights from US cities to Reykjavik, Iceland from only $300 roundtrip.

June 15, 2025

Chicago to Geneva, Switzerland for only $362 roundtrip

Cheap flights from Chicago to Geneva, Switzerland for only $362 roundtrip with Scandinavian Airlines.

June 15, 2025

SUMMER: US cities to Colombian cities from only $221 roundtrip

Summer flights from US cities to Colombian cities from only $221 roundtrip with Copa Airlines.

May 27, 2025

SUMMER: Chicago to the Dominican Republic for only $265 roundtrip

Summer flights from Chicago to the Dominican Republic for only $265 roundtrip with American Airlines.