Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Best option Chicago O'Hare Havana | Outbound 09/19/25 1 Stopover (IAH) UA2426, UA1506 18h 45min | Return 09/29/25 1 Stopover (IAH) UA1507, UA2013 07h 06min | | ![]() | ? | $386 | |
Chicago O'Hare Havana | Outbound 09/04/25 1 Stopover (IAH) UA2426, UA1506 18h 45min | Return 09/28/25 1 Stopover (IAH) UA1507, UA1752 07h 06min | | ![]() | ? | $390 | |
Chicago O'Hare Havana | Outbound 11/03/25 1 Stopover (MIA) AA2984, AA2705 06h 05min | Return 11/12/25 2 Stopovers (MIA, CLT) AA2696, AA2743, AA2514 12h 02min | | ![]() | ? | $419 | |
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 | | ![]() | ? | $422 | |
Chicago O'Hare Havana | Outbound 10/18/25 2 Stopovers (LGA, MIA) AA1166, AA1530, AA2705 14h 40min | Return 11/17/25 2 Stopovers (MIA, DCA) AA2706, AA2013, AA1187 10h 00min | | ![]() | ? | $437 | |
Chicago O'Hare Havana | Outbound 09/19/25 2 Stopovers (PHL, MIA) AA2970, AA1871, AA2481 11h 30min | Return 09/29/25 1 Stopover (IAH) UA1507, UA2013 07h 01min | | ![]() | ? | $462 | |
Chicago O'Hare Havana | Outbound 09/04/25 1 Stopover (IAH) UA1397, UA1506 07h 30min | Return 09/28/25 1 Stopover (IAH) UA1507, UA1752 07h 06min | | ![]() | ? | $478 | |
Chicago O'Hare Havana | Outbound 06/18/25 1 Stopover (MIA) AA0835, AA0837 05h 53min | Return 07/15/25 1 Stopover (MIA) AA2696, AA3056 10h 40min | | ![]() | ? | $486 | |
Chicago O'Hare Havana | Outbound 11/03/25 2 Stopovers (DCA, MIA) AA2345, AA1252, AA2481 09h 54min | Return 11/12/25 2 Stopovers (MIA, DCA) AA0243, AA3106, AA2048 09h 32min | | ![]() | ? | $487 | |
Chicago O'Hare Havana | Outbound 10/09/25 1 Stopover (IAH) UA0365, UA1506 07h 20min | Return 11/01/25 2 Stopovers (MIA, CLT) AA2678, AA3104, AA0536 09h 17min | | ![]() | ? | $488 |
Airline
- American Airlines
- United Airlines
- Aeroméxico
- Copa Airlines
Tips and tricks to help you find cheap flights from Chicago O'Hare to Havana
Favorite airline: Copa
100 % of bookings on this flight route are made with Copa, American Airlines and United Airlines.

Copa
48 %

American Airlines
45 %

United Airlines
7 %
Cheapest weekday: e.g. Friday
Compared to other weekdays, flights are cheapest on Thursday and Friday.
Favourite connection: via Panama City
58 % of booked tickets on this route are for flights with a transfer in Panama City.
Route
bookings
1 stopover Panama City-Tocumen International
13h 28min, from $406
58 %
1 stopover Miami International Airport, FL
17h 53min, from $1,115
25 %
1 stopover Houston - George Bush Intercontinental Airport, TX
16h 53min, from $1,093
8 %
Important flight information
Flight information: Chicago O'Hare - Havana
Roundtrip from | $385.66 |
---|---|
Distance | 2175 km |
Departure airport | Airport Chicago O'Hare International Airport, IL (ORD) |
Arrival airport | Airport Havana-Jose Marti International (HAV) |
Destination country | Flights to Cuba |
Alternative flights to Havana
- Flight Miami - Havana from $285
- Flight New York - Havana from $393
- Flight New York - Havana from $430
- Flight Chicago - Havana from $386
- Flight Houston - George Bush - Havana from $416
- Flight Orlando - Havana from $326
- Flight Tampa - Havana from $363
- Flight Fort Lauderdale - Havana from $356
- Flight Los Angeles - Havana from $419
- Flight Las Vegas - Havana from $403
Flight destinations with a similar price
- Flight Havana - Georgetown, Guyana from $680
- Flight Havana - Istanbul from $1,050
- Flight Havana - Holguin from $607
- Flight Havana - Frankfurt from $904
- Flight Havana - Santo Domingo from $458
- Flight Havana - Punta Cana from $536
- Flight Havana - Madrid from $710
- Flight Havana - Lima from $316
- Flight Havana - San Juan (Puerto Rico) from $369
Flight destinations with a similar price
- Flight Chicago O'Hare - Vienna from $390
- Flight Chicago O'Hare - London Heathrow from $413
- Flight Chicago O'Hare - Bridgetown from $401
- Flight Chicago O'Hare - Champaign from $355
- Flight Chicago O'Hare - White Plains-NY from $370
- Flight Chicago O'Hare - Santo Domingo from $358
- Flight Chicago O'Hare - Guayaquil from $354
- Flight Chicago O'Hare - Amsterdam from $353
- Flight Chicago O'Hare - Panama City from $413