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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 03/02/25 1 Stopover (IAH) UA2665, UA6306 15h 55min	Return 03/07/25 1 Stopover (IAH) UA6307, UA0668 08h 28min	United Airlines	?	$444
Chicago Havana	Outbound 12/13/24 2 Stopovers (CLT, MIA) AA2966, AA3068, AA0017 19h 15min	Return 12/31/24 1 Stopover (MIA) AA2696, AA1763 07h 00min	American Airlines	?	$464
Chicago Havana	Outbound 02/19/25 1 Stopover (MIA) AA1411, AA0837 05h 41min	Return 03/10/25 2 Stopovers (MIA, LGA) AA1334, AA1117, AA0359 11h 35min	American Airlines	?	$484