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
02/13/26
1 Stopover (MIA)
AA3015, AA0242
13h 21min
Return
02/26/26
2 Stopovers (MIA, LGA)
AA2706, AA3330, AA2041
09h 20min
American Airlines ?
$576
Best option
Chicago
Havana
Outbound
02/10/26
1 Stopover (PTY)
CM0229, CM0217
09h 28min
Return
02/16/26
1 Stopover (PTY)
CM0359, CM0235
11h 47min
Copa Airlines ?
$648
Chicago
Havana
Outbound
04/03/26
2 Stopovers (DCA, MIA)
AA1944, AA2648, AA0017
15h 23min
Return
04/16/26
1 Stopover (MIA)
AA2483, AA1140
06h 30min
American Airlines ?
$577
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
American Airlines ?
$586
Chicago
Havana
Outbound
02/13/26
1 Stopover (PTY)
CM0236, CM0387
14h 09min
Return
02/26/26
2 Stopovers (MIA, CLT)
AA2696, AA2822, AA2290
08h 41min
Copa Airlines ?
$587
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
American Airlines ?
$604
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 $ 575,41
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
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