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.

Flight schedule from Chicago (CHI) to Havana (HAV)

Select a travel date in the flight schedule for the route from Chicago (CHI) to Havana (HAV) and compare affordable flight deals.

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Matching outbound flights1 of 1
fromto
dep.arr.
durationstopovers
  1. August 9 – 15, 2026
  2. August 16 – 22, 2026
  3. August 23 – 29, 2026
    1. ORDHAV
      1 stopover
      1. American Airlines

      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
      Alternative flights to Havana
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