| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Best option Chicago Havana | Outbound 09/19/25 1 Stopover (IAH) UA2426, UA1506 18h 45min | Return 09/29/25 1 Stopover (IAH) UA1507, UA2013 07h 06min |  United Airlines |  | ? | $386 | |
| Chicago Havana | Outbound 09/04/25 1 Stopover (IAH) UA2426, UA1506 18h 45min | Return 09/28/25 1 Stopover (IAH) UA1507, UA1752 07h 06min | United Airlines | | ? | $390 | |
| 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 | |
| Chicago Havana | Outbound 09/23/25 1 Stopover (MIA) AA2984, AA2705 06h 05min | Return 09/30/25 2 Stopovers (MIA, PHL) AA1334, AA3060, AA1327 12h 06min | American Airlines | | ? | $445 | |
| Chicago Havana | Outbound 10/18/25 2 Stopovers (DFW, MIA) AA2499, AA2090, AA2699 13h 14min | Return 10/24/25 2 Stopovers (MIA, CLT) AA1334, AA1521, AA0815 10h 40min | American Airlines | | ? | $446 | |
| Chicago 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 | American Airlines |  | ? | $462 | |
| Chicago Havana | Outbound 09/04/25 1 Stopover (IAH) UA1397, UA1506 07h 30min | Return 09/28/25 1 Stopover (IAH) UA1507, UA1752 07h 06min | United Airlines | | ? | $478 | |
| 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 10/09/25 1 Stopover (IAH) UA0365, UA1506 07h 20min | Return 11/01/25 2 Stopovers (MIA, CLT) AA2678, AA3104, AA0536 09h 17min | United Airlines | | ? | $488 | |
| 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 |
Airline
- American Airlines
- United Airlines
- Aeroméxico
- 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
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 | $ 385,66 |
|---|---|
| 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 Miami - Havana from $ 285
- Flight New York - Havana from $ 401
- Flight New York - Havana from $ 430
- Flight Chicago O'Hare - Havana from $ 386
- Flight Houston - George Bush - Havana from $ 416
- Flight Newark - Havana from $ 401
- Flight Tampa - Havana from $ 365
- Flight Fort Lauderdale - Havana from $ 360
- Flight Los Angeles - Havana from $ 419
- Flight Las Vegas - Havana from $ 403
Flight destinations with a similar price
- Flight Havana - Georgetown, Guyana from $ 684
- Flight Havana - Frankfurt from $ 904
- Flight Havana - Holguin from $ 607
- Flight Havana - Santo Domingo from $ 482
- Flight Havana - Lima from $ 316
- Flight Havana - San Juan (Puerto Rico) from $ 380
- Flight Havana - Istanbul from $ 1.112
- Flight Havana - Madrid from $ 710
- Flight Havana - Punta Cana from $ 536