| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Chicago 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 | |
| Best option Chicago Havana | Outbound 06/18/25 1 Stopover (MIA) AA0835, AA0837 05h 53min | Return 07/15/25 1 Stopover (MIA) AA2696, AA3056 10h 40min | American Airlines |  | ? | $486 | |
| Chicago 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 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 06/18/25 1 Stopover (PTY) CM0229, CM0217 09h 43min | Return 07/15/25 2 Stopovers (MIA, CLT) AA2706, AA0400, AA0815 09h 25min |  Copa Airlines |  | ? | $498 | |
| Chicago Havana | Outbound 06/08/25 1 Stopover (MIA) AA3304, AA2481 06h 12min | Return 06/12/25 1 Stopover (IAH) UA1507, UA0787 08h 38min | American Airlines |  | ? | $510 | |
| 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 04/12/25 1 Stopover (PTY) CM0236, CM0217 16h 59min | Return 04/27/25 1 Stopover (IAH) UA1507, UA0787 07h 38min | Copa Airlines | | ? | $543 | |
| Chicago Havana | Outbound 04/12/25 1 Stopover (IAH) UA2665, UA1506 16h 40min | Return 04/27/25 1 Stopover (IAH) UA1507, UA2616 17h 50min | United Airlines | | ? | $570 | |
| 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 |
Airline
- American Airlines
- United Airlines
- Copa Airlines
- Aeroméxico
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
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 - Havana
| Roundtrip from | $ 421,10 |
|---|---|
| Distance | 2159 km |
| Departure airport | Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI) |
| Arrival airport | Airport Havana-Jose Marti International (HAV) |
| Destination country | Flights to Cuba |
Alternative flights to Havana
- Flight Newark - Havana from $ 430
- Flight New York - Havana from $ 430
- Flight Los Angeles - Havana from $ 456
- Flight Houston - George Bush - Havana from $ 416
- Flight San Francisco - Havana from $ 513
- Flight Baltimore - Havana from $ 315
- Flight New York - Havana from $ 430
- Flight Chicago O'Hare - Havana from $ 422
- Flight Orlando - Havana from $ 381
- Flight Fort Lauderdale - Havana from $ 360
Flight destinations with a similar price
- Flight Havana - Managua from $ 538
- Flight Havana - Georgetown, Guyana from $ 691
- Flight Havana - Istanbul from $ 1.112
- Flight Havana - Holguin from $ 607
- Flight Havana - Madrid from $ 718
- Flight Havana - Frankfurt from $ 976
- Flight Havana - Lima from $ 316
- Flight Havana - San Juan (Puerto Rico) from $ 394
- Flight Havana - Santo Domingo from $ 516
- Flight Havana - Punta Cana from $ 528
Flight destinations with a similar price
- Flight Chicago - Montego Bay from $ 403