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
Best option
Chicago
Havana
Outbound
09/19/25
1 Stopover (IAH)
UA2426, UA1506
18h 45min
Return
09/29/25
1 Stopover (IAH)
UA1507, UA2013
07h 06min
United Airlines ?
$386
Chicago
Havana
Outbound
09/04/25
1 Stopover (IAH)
UA2426, UA1506
18h 45min
Return
09/28/25
1 Stopover (IAH)
UA1507, UA1752
07h 06min
United Airlines ?
$390
Chicago
Havana
Outbound
11/03/25
1 Stopover (MIA)
AA2984, AA2705
06h 05min
Return
11/12/25
2 Stopovers (MIA, CLT)
AA2696, AA2743, AA2514
12h 02min
American Airlines ?
$419
Chicago
Havana
Outbound
10/18/25
2 Stopovers (LGA, MIA)
AA1166, AA1530, AA2705
14h 40min
Return
11/17/25
2 Stopovers (MIA, DCA)
AA2706, AA2013, AA1187
10h 00min
American Airlines ?
$437
Chicago
Havana
Outbound
09/19/25
2 Stopovers (PHL, MIA)
AA2970, AA1871, AA2481
11h 30min
Return
09/29/25
1 Stopover (IAH)
UA1507, UA2013
07h 01min
American Airlines ?
$462
Chicago
Havana
Outbound
09/04/25
1 Stopover (IAH)
UA1397, UA1506
07h 30min
Return
09/28/25
1 Stopover (IAH)
UA1507, UA1752
07h 06min
United Airlines ?
$478
Chicago
Havana
Outbound
11/03/25
2 Stopovers (DCA, MIA)
AA2345, AA1252, AA2481
09h 54min
Return
11/12/25
2 Stopovers (MIA, DCA)
AA0243, AA3106, AA2048
09h 32min
American Airlines ?
$487
Chicago
Havana
Outbound
10/09/25
1 Stopover (IAH)
UA0365, UA1506
07h 20min
Return
11/01/25
2 Stopovers (MIA, CLT)
AA2678, AA3104, AA0536
09h 17min
United Airlines ?
$488
Chicago
Havana
Outbound
10/10/25
1 Stopover (MIA)
AA3213, AA0252
05h 35min
Return
11/04/25
2 Stopovers (MIA, CLT)
AA0243, AA3104, AA3178
07h 58min
American Airlines ?
$495
Chicago
Havana
Outbound
09/19/25
1 Stopover (IAH)
UA2432, UA1506
17h 25min
Return
09/29/25
1 Stopover (IAH)
UA1507, UA2616
17h 50min
United Airlines ?
$862
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 $385.66
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 destinations with a similar price
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