Flights from Chicago to Cuba

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.

Outbound Return Airlines Shop Baggage Price
Best option
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
Chicago
Havana
Outbound
06/20/25
1 Stopover (IAH)
UA1397, UA1506
07h 20min
Return
07/19/25
2 Stopovers (MIA, PHL)
AA1334, AA3060, AA1327
11h 49min
United Airlines ?
$537
Chicago
Havana
Outbound
06/20/25
1 Stopover (MIA)
AA1250, AA2481
08h 10min
Return
07/19/25
2 Stopovers (MIA, PHL)
AA2678, AA3060, AA1327
14h 14min
American Airlines ?
$588
Prices based on recent searches, subject to last-minute changes
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