Our cheapest offers for flights from Chicago to Cuba

Here you can compare cheap flights from Chicago (CHI) to Cuba for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Cuba. Prices and availability may change at any time.

Flights from Chicago (CHI) to Havana (HAV)

	Outbound	Return	Airlines	Baggage	Price
Chicago Havana	Outbound 04/21/25 2 Stopovers (CLT, MIA) AA2946, AA3068, AA0017 14h 35min	Return 05/19/25 1 Stopover (MIA) AA0838, AA1919 09h 17min	American Airlines	?	$435
Chicago Havana	Outbound 06/08/25 1 Stopover (IAH) UA1115, UA1506 16h 50min	Return 06/12/25 1 Stopover (IAH) UA1507, UA2616 17h 48min	United Airlines	?	$447
Chicago Havana	Outbound 06/20/25 1 Stopover (MIA) AA1277, AA0242 13h 36min	Return 07/19/25 1 Stopover (MIA) AA2678, AA3056 09h 50min	American Airlines	?	$481