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

Find Transport to Key West (Island)

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There are 7 ways to get from Chicago to Key West (Island) by plane, bus (Greyhound, Flixbus), train, shuttle, or car

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
    5h 5m
    $92–405

  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
    $235–452

  3. Train, shuttle

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain train Floridian
    2. Take a shuttle bus from Miami, FL - International Airport to Key West, FLshuttle bus To the Keys
    2d 4h
    $846–1,532

  4. Drive 1,468.1 mi

    1. Drive from Chicago to Key Westcar car 1,468.1 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
    6h 49m
    $112–555

  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 54m
    $123–564

  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 53m
    $160–669

Chicago to Key West (Island) by bus

Calendar14Weekly Buses
Duration36h 5mAverage Duration
Ticket$235Cheapest 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: 5h 5m

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) every 4 hours. 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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