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
01/16/25
1 Stopover (IAH)
UA1568, UA1506
19h 35min
Return
01/20/25
1 Stopover (IAH)
UA1507, UA0685
08h 00min
United Airlines ?
$412
Chicago
Havana
Outbound
01/16/25
1 Stopover (IAH)
UA1600, UA1506
07h 40min
Return
01/20/25
1 Stopover (IAH)
UA1507, UA0685
08h 00min
United Airlines ?
$498
Chicago
Havana
Outbound
01/16/25
1 Stopover (MEX)
AM0689, AM0451
12h 57min
Return
01/20/25
2 Stopovers (MEX, GDL)
AM0452, AM0256, AM0652
19h 51min
Aeroméxico ?
$691
Prices based on recent searches, subject to last-minute changes
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* Prices may vary, please check the travel details given by the online travel agency before booking. Prices include taxes.