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How to get fromChicago to Key West (Island)by plane, bus (Greyhound, Flixbus), train, bus, car, or bus (Greyhound)

Find Transport to Key West (Island)

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There are 8 ways to get from Chicago to Key West (Island) by plane, bus (Greyhound, Flixbus), train, bus, car, or bus (Greyhound)

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 from Chicago O'Hare International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    4h 57m
    $78–365

  2. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Miami Airport Stationbus bus
    3. Take the bus from Miami Airport Station to Key West Airportbus bus
    36h 5m
    $216–427

  3. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain train Floridian
    2. Take the bus from Miami Airport Station to Key West Airportbus bus Greyhound US0720s
    2d 4h
    $570–1,250

  4. Drive  1,466.6 mi

    1. Drive from Chicago to Key Westcar car 1,466.6 mi
    27h 7m
    $268–387

  5. Fly from Chicago Midway International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)plane plane MDW - EYW
    7h 4m
    $102–485

  6. Train to South Bend, fly

    1. Take the train from Van Buren St. to South Bend Airporttrain train
    2. Fly from South Bend (SBN) to Key West International Airport (EYW)plane plane SBN - EYW
    7h 51m
    $103–444

  7. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain train
    2. Fly from General Mitchell International Airport (MKE) to Key West International Airport (EYW)plane plane MKE - EYW
    7h 55m
    $145–664

  8. Bus via Pembroke Pines (Greyhound)

    1. Take the bus from Chicago Train Station to Atlanta Bus Stationbus bus
    2. Take the bus from Atlanta Bus Station to Hollywood Sheridan Trirail Stationbus bus
    3. Take the bus from Miami Airport Station to Key West Airportbus bus
    40h 21m
    $221–422

Chicago to Key West (Island) by bus

Calendar14Weekly Buses
Duration36h 5mAverage Duration
Ticket$216Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Key West (Island).ExpandLaunch map view
  • Distance: 1,272.1 mi
  • Duration: 4h 57m

What companies run services between Chicago, IL, USA and Key West (Island), FL, USA?

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Key West Airport via Atlanta Bus Station and Miami Airport Station in around 36h 5m.

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