Flight Routes from Chicago to Havana

Compare cheap outbound and return flights from Chicago (CHI) to Havana (HAV) and find the best offer from numerous airlines and travel agencies.

Trip type
Flight distance
2,159 km
Time difference
Airports in Chicago
  1. O'Hare International Airport, IL
  2. Midway International Airport, IL
  3. Rockford, IL

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.

offers
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Matching outbound flights0 of 0
fromto
dep.arr.
durationstopovers
  1. September 6 – 12, 2026
  2. September 13 – 19, 2026
  3. September 20 – 26, 2026
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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

        Discover more flights around Chicago and Havana

        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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