| 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 02/19/25 1 Stopover (MIA) AA1411, AA0837 05h 41min | Return 03/10/25 2 Stopovers (MIA, LGA) AA1334, AA1117, AA0359 11h 35min |  American Airlines | | ? | $484 | |
| 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 02/19/25 2 Stopovers (LGA, MIA) AA2079, AA2052, AA2481 09h 12min | Return 03/10/25 1 Stopover (MIA) AA0253, AA0581 14h 19min | American Airlines | | ? | $511 | |
| 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 | |
| Chicago Havana | Outbound 02/19/25 1 Stopover (MEX) AM0689, AM0451 12h 57min | Return 03/10/25 1 Stopover (MEX) AM0452, AM0686 22h 42min | Aeroméxico | | ? | $867 |
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Find cheap flights -
Booking tips
- Flight Routes
- Flights to Cuba
- Flights to Havana
- Flights Chicago (CHI) Havana (HAV)
Airline
- American Airlines
- United Airlines
- Aeroméxico
Flight type
- Return
Outbound departure month
- January 2025
- February 2025
Outbound weekday
- Wednesday
- Thursday
Return departure month
- January 2025
- March 2025
Return weekday
- Monday
Change in
- Miami International Airport, FL
- Houston - George Bush Intercontinental Airport, TX
- Mexico City-Juarez International
- New York - La Guardia Airport, NY
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 %
Flight information: Chicago - Havana
| Roundtrip from | $411.96 |
|---|---|
| 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 New York - Havana from $643
- Flight Miami - Havana from $293
- Flight New York - Havana from $369
- Flight Orlando - Havana from $360
- Flight Baltimore - Havana from $289
- Flight Newark - Havana from $369
- Flight San Francisco - Havana from $433
- Flight Chicago O'Hare - Havana from $412
- Flight Houston - George Bush - Havana from $419
- Flight Tampa - Havana from $319
Flight destinations with a similar price
- Flight Havana - Managua from $525
- Flight Havana - Georgetown, Guyana from $751
- Flight Havana - Holguin from $684
- Flight Havana - Santiago de Cuba from $586
- Flight Havana - Cancun from $329
- Flight Havana - Port of Spain from $581
- Flight Havana - Frankfurt from $824
- Flight Havana - Istanbul from $940
- Flight Havana - Lima from $554
- Flight Havana - La Isabela from $970
Flight destinations with a similar price
- Flight Chicago - Honolulu from $391
- Flight Chicago - Vienna from $441
- Flight Chicago - Munich from $415
- Flight Chicago - Berlin from $407
- Flight Chicago - Frankfurt from $423
- Flight Chicago - Dublin from $379
- Flight Chicago - London from $451