Cheap flights from Havana to Chicago

Flights overview

Useful information for finding cheap flights from Havana to Chicago and booking your next trip
Cheapest one-way flight $244
Delta 2 stops 9 hr Wed, Jul 8
The cheapest one-way flight from Havana to Chicago is currently $244
Fastest flight 6 hr 15 min The fastest flight with stops from Havana to Chicago takes 6 hr 15 min
Nonstop flights None There are no direct flights on this route.

Popular airlines from Havana to Chicago

  • American
    763 weekly connecting flights
    HAV - ORD Every day
  • Southwest
    514 weekly connecting flights
    HAV - MDW, ORD Every day
  • Delta
    119 weekly connecting flights
    HAV - MDW, ORD Every day

Popular airports near Havana

  • José Martí international Airport (HAV) (HAV)
    Havana Cuba 32 min 10 mi
  • Juan Gualberto Gómez International Airport (VRA)
    Varadero Cuba 1 hr 55 min 59 mi
  • International Airport "Abel Santamaría Cuadrado" of Santa Clara (SNU)
    Santa Clara Cuba 3 hr 42 min 160 mi

Popular airports near Chicago

  • Chicago O'Hare International Airport (ORD)
    Chicago United States 26 min 16 mi
  • Chicago Midway International Airport (MDW)
    Chicago United States 25 min 9 mi
  • Milwaukee Mitchell International Airport (MKE)
    Milwaukee United States 1 hr 23 min 75 mi
  • Indianapolis International Airport (IND)
    Indianapolis United States 2 hr 58 min 165 mi

Frequently asked questions about flying from Havana to Chicago

The cheapest one-way flight was with Delta from $244.

Some of the cheapest round-trip deals we found with different airlines:
    The cheapest one-way flight starts at $244 and departs on Wed, Jul 8.
    6 hr 15 min is the shortest flight time from Havana to Chicago.
    Chicago's peak season is Jun–Aug. Popular events throughout year include St. Patrick's Day, when the river is tinted green (Mar 17); the Pride Parade (Jun); the Taste of Chicago culinary festival (Jul) and the Jazz Festival (Sep). During the holiday season (Nov–Dec), the Magnificent Mile Lights Festival and Christkindlmarket, a German Christmas market in Daley Plaza, draw crowds to the city.
    It's easy to use Google Flights to find the cheapest days to fly from Havana to Chicago.
    Just click the Departure label near the top of the page to open the calendar. Choose a start date and a return date to see how the round-trip fare changes on those specific days.
    Adjust the trip type to see one-way fares. The cheapest available flights are highlighted and easy to spot. Once you settle on dates, click the Search button to see flight options and book the deal.

    You can also turn on price tracking to get alerts if the price changes for a route or flight.
    What counts as the best airline for your flights from Havana to Chicago really depends on your individual needs. You may have a favorite carrier or a loyalty program you like, but price, convenience, and airports served also come into play. Flexibility and booking terms – Can you change flights if you want to stay longer or get a refund if you have to postpone your trip? – are also factors that help determine which airline is best to fly from Havana to Chicago.

    In terms of flights, American is the most popular. American offers 763 connecting flights per week. American flies from José Martí international Airport (HAV) (HAV) to Chicago O'Hare International Airport (ORD) .

    Other popular airlines flying from Havana to Chicago are:
    • Southwest offers 514 connecting flights per week. Southwest flies from José Martí international Airport (HAV) (HAV) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
    • Delta offers 119 connecting flights per week. Delta flies from José Martí international Airport (HAV) (HAV) to Chicago Midway International Airport (MDW) , Chicago O'Hare International Airport (ORD) .
    The number of connecting flights refers to distinct flights with at least one stop between Havana and Chicago.
    The cheapest one-way flight was with Delta from $244.

    Some of the cheapest round-trip deals we found with different airlines:
      No airline flies direct from Havana to Chicago.
      • There are 763 American connecting flights from Havana to Chicago per week. Flights are available every day.
      • There are 514 Southwest connecting flights from Havana to Chicago per week. Flights are available every day.
      • There are 119 Delta connecting flights from Havana to Chicago per week. Flights are available every day.
      Use the Stops filter while searching for flights, to see only nonstop options in your results.
      The cheapest last-minute deal between Havana and Chicago at price $562 is offered by Delta from Thu, May 7 to Mon, May 11.
      No airline flies direct from Havana to Chicago.
      • There are 763 American connecting flights from Havana to Chicago per week. Flights are available every day.
      • There are 514 Southwest connecting flights from Havana to Chicago per week. Flights are available every day.
      • There are 119 Delta connecting flights from Havana to Chicago per week. Flights are available every day.
      Use the Stops filter while searching for flights, to see only nonstop options in your results.
      There are no direct flights from Havana to Chicago.
      It's easy to find nonstop flights with Google Flights! Once you've searched for flights from Havana to Chicago, just select the nonstop flights only option in the 'Stops’ filter in the search form and view all available direct flights and their prices.
      To book business class trips from Havana to Chicago, look for the default Economy selection at the top, and change it to your desired cabin class such as Premium Economy, Business Class, or First Class. You can then select your departure and arrival dates, consider available options, and book your business travel.

      You can also adjust the trip type to view one-way fares.
      The best last-minute getaway deal for the next weekend between Havana and Chicago starts at $562 from Thu, May 7 to Mon, May 11 with Delta.
      The cheapest last-minute deal between Havana and Chicago at price $562 is offered by Delta from Thu, May 7 to Mon, May 11.
      To find last-minute flight deals from Havana to Chicago, start by entering the city names, select the desired departure and return dates, and hit the Search button to view flight options.

      You can check for last-minute flights for the same day or adjust the trip type to see one-way fares.

      Search more flights

      Popular trips from Havana

      1. London
        $1,601
        May 14 — May 20
        1 stop 17 hr 45 min Aeromexico
      2. New York
        $534
        May 8 — May 16
        2 stops 6 hr 10 min American
      3. Paris
        $1,460
        Jun 15 — Jun 22
        1 stop 20 hr 42 min Air France, COPA
      4. Singapore
        May 3 — May 9

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