Flights from Chicago O'Hare to Cuba

Our cheapest offers for flights from Chicago O'Hare to Cuba

Here you can compare cheap flights from Chicago O'Hare (ORD) 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.

Outbound Return Airlines Shop Baggage Price
Chicago O'Hare
Havana
Outbound
06/18/25
2 Stopovers (LGA, MIA)
AA0327, AA2850, AA2481
10h 25min
Return
07/15/25
1 Stopover (MIA)
AA0253, AA2194
06h 20min
American Airlines ?
$422
Chicago O'Hare
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 O'Hare
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
Prices based on recent searches, subject to last-minute changes
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