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How to get fromHavana to Chicagoby plane or bus

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There are 3 ways to get from Havana to Chicago by plane or bus

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Fly José Martí International Airport to Chicago Midway International Airport

    best
    1. Fly from José Martí International Airport (HAV) to Chicago Midway International Airport (MDW)plane plane HAV - MDW
    8h 40m
    $208–967

  2. Bus to Juan Gualberto Gómez International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the bus from Terminal de Ómnibus Nacionales La Habana to Varadero Airportbus bus
    2. Fly from Juan Gualberto Gómez International Airport (VRA) to Chicago O'Hare International Airport (ORD)plane plane VRA - ORD
    12h 17m
    $109–452

  3. Fly José Martí International Airport to Chicago O'Hare International Airport

    1. Fly from José Martí International Airport (HAV) to Chicago O'Hare International Airport (ORD)plane plane HAV - ORD
    9h 9m
    $178–817

José Martí International Airport (HAV) to Chicago Midway International Airport (MDW) flights

Calendar14Weekly Planes
Duration6h 38mAverage Duration
Ticket$207Cheapest Price
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Questions & Answers

Map of how to get from Havana to Chicago.ExpandLaunch map view
  • Distance: 1,355.8 mi
  • Duration: 8h 40m

What companies run services between Havana, Cuba and Chicago, IL, USA?

Southwest Airlines, American Airlines, and Viva Aerobus fly from José Martí International Airport (HAV) to Chicago Midway International Airport (MDW) twice daily.

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