Flights from Chicago to Havana

Trip type

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
Best option
Chicago
Havana
Outbound
05/16/26
1 Stopover (MIA)
AA1694, AA2699
11h 20min
Return
05/29/26
1 Stopover (MIA)
AA2706, AA3056
07h 44min
American Airlines ?
$586
Chicago
Havana
Outbound
07/26/26
1 Stopover (MIA)
AA2690, AA0017
13h 35min
Return
08/05/26
1 Stopover (MIA)
AA2696, AA1159
10h 37min
American Airlines ?
$596
Chicago
Havana
Outbound
03/28/26
1 Stopover (MIA)
AA2901, AA0017
12h 21min
Return
04/25/26
1 Stopover (MIA)
AA2706, AA0791
09h 35min
American Airlines ?
$604
Chicago
Havana
Outbound
05/16/26
1 Stopover (MIA)
AA1694, AA2699
11h 20min
Return
05/29/26
1 Stopover (MIA)
AA2706, AA3304
09h 13min
American Airlines ?
$1,502
Chicago
Havana
Outbound
03/28/26
1 Stopover (MIA)
AA2901, AA0017
12h 21min
Return
04/25/26
1 Stopover (MIA)
AA2678, AA1486
27h 49min
American Airlines ?
$1,522
Chicago
Havana
Outbound
07/26/26
1 Stopover (MIA)
AA2690, AA0017
13h 35min
Return
08/05/26
1 Stopover (MIA)
AA2696, AA1211
16h 37min
American Airlines ?
$3,521
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 US$
58 %
1 stopover Miami International Airport, FL
17h 53min, from 1 115 US$
25 %
1 stopover Houston - George Bush Intercontinental Airport, TX
16h 53min, from 1 093 US$
8 %

Important flight information

Flight information: Chicago - Havana

Roundtrip from 586,00 US$
Distance 2159 km
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Havana-Jose Marti International (HAV)
Destination country Flights to Cuba
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