For winter travel, fly from Chicago to Havana for $261 roundtrip on American.

We found seats departing ORD on Wednesday, January 30, returning from HAV on Wednesday, February 6. Flights connect via Miami MIA.

Other dates are available for travel throughout February.

See our Chicago ORD fare listings for a complete look at current finds.

Intro image by Delpixel via Shutterstock

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