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How to get fromChicago to Guantánamo Bayby plane, bus, unknown, car, car ferry, shuttle, or train

Find Transport to Guantánamo Bay

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There are 9 ways to get from Chicago to Guantánamo Bay by plane, bus, unknown, car, car ferry, shuttle, or train

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 Chicago O'Hare International Airport to Antonio Maceo International Airport, bus, travel

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Antonio Maceo International Airport (SCU)plane plane ORD - SCU
    2. Take the bus from Santiago de Cuba to Guantanamobus bus
    3. Walk from Guantanamo to Guantánamo Bayunknown unknown
    20h 16m

  2. Drive, car ferry, travel

    1. Drive from Chicago to Scotland Wharfcar car
    2. Take the carferry from Scotland Wharf to Jamestowncarferry car ferry
    3. Walk from Jamestown to Guantánamo Bayunknown unknown
    2d 5h

  3. Fly Chicago Midway International Airport to Antonio Maceo International Airport, bus, travel

    1. Fly from Chicago Midway International Airport (MDW) to Antonio Maceo International Airport (SCU)plane plane MDW - SCU
    2. Take the bus from Santiago de Cuba to Guantanamobus bus
    3. Walk from Guantanamo to Guantánamo Bayunknown unknown
    18h 58m

  4. Fly Chicago O'Hare International Airport to Sangster International Airport, travel

    1. Fly from Chicago O'Hare International Airport (ORD) to Sangster International Airport (MBJ)plane plane ORD - MBJ
    2. Walk from Montego-Bay-Airport-MBJ to Guantánamo Bayunknown unknown
    13h 41m

  5. Fly Chicago O'Hare International Airport to Providenciales International Airport, travel

    1. Fly from Chicago O'Hare International Airport (ORD) to Providenciales International Airport (PLS)plane plane ORD - PLS
    2. Walk from Providenciales-Airport-PLS to Guantánamo Bayunknown unknown
    13h 49m

  6. Fly Chicago Midway International Airport to Sangster International Airport, travel

    1. Fly from Chicago Midway International Airport (MDW) to Sangster International Airport (MBJ)plane plane MDW - MBJ
    2. Walk from Montego-Bay-Airport-MBJ to Guantánamo Bayunknown unknown
    14h 50m

  7. Fly Chicago O'Hare International Airport to Frank País International Airport, shuttle, bus, travel

    1. Fly from Chicago O'Hare International Airport (ORD) to Frank País International Airport (HOG)plane plane ORD - HOG
    2. Take a shuttle bus from Hotel Pernik Holguin to Melia Santiago de Cubashuttle bus
    3. Take the bus from Santiago de Cuba to Guantanamobus bus
    4. Walk from Guantanamo to Guantánamo Bayunknown unknown
    15h 46m

  8. Fly Chicago Midway International Airport to Frank País International Airport, shuttle, bus, travel

    1. Fly from Chicago Midway International Airport (MDW) to Frank País International Airport (HOG)plane plane MDW - HOG
    2. Take a shuttle bus from Hotel Pernik Holguin to Melia Santiago de Cubashuttle bus
    3. Take the bus from Santiago de Cuba to Guantanamobus bus
    4. Walk from Guantanamo to Guantánamo Bayunknown unknown
    26h 24m

  9. Train to Detroit, fly to Providenciales International Airport, travel

    1. Take the train from Chicago Union Station to Dearborntrain train
    2. Fly from Detroit (DTW) to Providenciales International Airport (PLS)plane plane DTW - PLS
    3. Walk from Providenciales-Airport-PLS to Guantánamo Bayunknown unknown
    18h 26m

Chicago O'Hare International Airport (ORD) to Antonio Maceo International Airport (SCU) flights

Calendar20Weekly Planes
Duration16h 17mAverage Duration
Ticket$165Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Guantánamo Bay.ExpandLaunch map view
  • Distance: 2,832 km
  • Duration: 20h 16m

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

There is no direct connection from Chicago to Guantánamo Bay. However, you can take the subway to O'Hare, walk to Chicago O'Hare International Airport (ORD) airport, fly to Antonio Maceo International Airport (SCU), walk to Santiago Airport, take the bus to La Colonia, walk to Santiago de Cuba, take the bus to Guantanamo, then travel to Guantánamo Bay. Alternatively, you can take a vehicle from Chicago to Guantánamo Bay via Scotland Wharf and Jamestown in around 2d 5h.

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