Outbound | Return | Airlines | Shop | Baggage | Price | ||
---|---|---|---|---|---|---|---|
Chicago Havana | Outbound 11/09/25 1 Stopover (PTY) CM0236, CM0217 16h 54min | Return 12/07/25 1 Stopover (PTY) CM0372, CM0228 26h 25min | | ![]() | ? | $482 | |
Best option Chicago Havana | Outbound 11/09/25 1 Stopover (PTY) CM0229, CM0217 09h 43min | Return 12/07/25 1 Stopover (PTY) CM0388, CM0235 17h 31min | | ![]() | ? | $534 | |
Chicago Havana | Outbound 11/09/25 2 Stopovers (CLT, MIA) AA1632, AA3184, AA0252 10h 15min | Return 12/07/25 1 Stopover (MIA) AA0838, AA1219 10h 57min | | ![]() | ? | $506 | |
Chicago Havana | Outbound 03/01/26 2 Stopovers (CLT, MIA) AA1632, AA1002, AA0837 07h 30min | Return 03/06/26 2 Stopovers (MIA, CLT) AA0838, AA1596, AA1039 10h 14min | | ![]() | ? | $586 | |
Chicago Havana | Outbound 03/02/26 2 Stopovers (CLT, MIA) AA3178, AA1990, AA0017 12h 55min | Return 03/09/26 2 Stopovers (MIA, LGA) AA2706, AA3330, AA2041 09h 20min | | ![]() | ? | $604 | |
Chicago Havana | Outbound 02/10/26 1 Stopover (PTY) CM0229, CM0217 09h 28min | Return 02/16/26 1 Stopover (PTY) CM0359, CM0235 11h 47min | | ![]() | ? | $648 |
Airline
- American Airlines
- Copa Airlines
Tips and tricks to help you find cheap flights from Chicago to Havana
Favorite airline: Copa
48 % of flights from Chicago to Havana are booked with Copa.

Copa
48 %

American Airlines
45 %

United Airlines
7 %
Cheapest weekday: e.g. Friday
Cheap flights on this route are operated on Thursday and Friday.
Favourite connection: via Panama City
Stopover flights on this route are especially popular via Panama City, making up 58 % of bookings.
Route
bookings
1 stopover Panama City-Tocumen International
13h 28min, from 406 $US
58 %
1 stopover Miami International Airport, FL
17h 53min, from 1 115 $US
25 %
1 stopover Houston - George Bush Intercontinental Airport, TX
16h 53min, from 1 093 $US
8 %
Important flight information
Flight information: Chicago - Havana
Roundtrip from | 481,06 $US |
---|---|
Distance | 2159 km |
Departure airport | Airport Chicago-IL, all airports (CHI) |
Arrival airport | Airport Havana-Jose Marti International (HAV) |
Destination country | Flights to Cuba |
Alternative flights to Havana
- Flight New York - Havana from 480 $US
- Flight New York - Havana from 796 $US
- Flight Chicago O'Hare - Havana from 482 $US
- Flight Newark - Havana from 480 $US
- Flight Baltimore - Havana from 407 $US
Flight destinations with a similar price
- Flight Havana - Georgetown, Guyana from 318 $US
- Flight Havana - Santo Domingo from 242 $US
- Flight Havana - Punta Cana from 273 $US
- Flight Havana - Madrid from 769 $US
- Flight Havana - Cancun from 297 $US
- Flight Havana - Istanbul from 1 145 $US
Flight destinations with a similar price
- Flight Chicago - Honolulu from 459 $US
- Flight Chicago - Vienna from 496 $US
- Flight Chicago - London from 438 $US
- Flight Chicago - Berlin from 507 $US
- Flight Chicago - Frankfurt from 444 $US
- Flight Chicago - Munich from 453 $US
- Flight Chicago - Hamburg from 510 $US
- Flight Chicago - Amsterdam from 435 $US