Flight Routes 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
Chicago
Havana
Outbound
08/20/26
2 Stopovers (JFK, MIA)
AA4536, AA1922, AA0242
19h 50min
Return
08/25/26
2 Stopovers (MIA, LGA)
AA0243, AA0552, AA0392
23h 35min
American Airlines ?
$625
Best option
Chicago
Havana
Outbound
08/20/26
1 Stopover (MIA)
AA2984, AA0837
07h 50min
Return
08/25/26
1 Stopover (MIA)
AA2483, AA0483
07h 10min
American Airlines ?
$1,039
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 $625.00
Distance 2159 km
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport Havana-Jose Marti International (HAV)
Destination country Flights to Cuba
Departure airport - Destination country Chicago-IL, all airports - Cuba
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