Cheapest return flights from Chicago to Havana in October from $354

AirHint found the following cheapest return flights from Chicago (ORD) to Havana (HAV) in October 2025 (see full year).

Return flights

22 Oct - 30 Oct Copa
22 Oct - 25 Oct Copa
09 Oct - 13 Oct American Airlines

Also check the deals for one-way flights from Chicago to Havana in October.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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