Flights from Chicago to Havana

Our cheapest offers for flights from Chicago to Havana

Here you can compare cheap flights from Chicago (CHI) to Havana (HAV) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to Havana. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
Havana
Outbound
04/21/25
2 Stopovers (CLT, MIA)
AA2946, AA3068, AA0017
14h 35min
Return
05/19/25
1 Stopover (MIA)
AA0838, AA1919
09h 17min
American Airlines ?
$435
Best option
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
found 3 days ago
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
found 3 days ago
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
06/20/25
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
Chicago
Havana
Outbound
04/21/25
2 Stopovers (GDL, MEX)
AM0653, AM0263, AM0451
25h 30min
Return
05/19/25
2 Stopovers (MEX, GDL)
AM0452, AM0260, AM0652
20h 20min
Aeroméxico ?
$878
Chicago
Havana
Outbound
06/08/25
1 Stopover (MIA)
AA3304, AA2481
06h 12min
Return
06/12/25
1 Stopover (MIA)
AA2706, AA2194
09h 15min
American Airlines ?
$1,830
found 3 days ago
Prices based on recent searches, subject to last-minute changes
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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 $ 434,24
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
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