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How to get fromChicago to Key West (Island)by plane, bus (Flixbus, Greyhound), 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 (Flixbus, Greyhound), 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
    5h 4m
    $122–555

  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
    34h 25m
    $157–362

  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
    $336–545

  4. Drive 1,468.3 mi

    1. Drive from Chicago to Key Westcar car 1,468.3 mi
    27h 6m
    $268–388

  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 9m
    $162–805

  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
    8h 3m
    $203–964

  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
    8h 20m
    $234–1,116

  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 31m
    $170–342

Chicago to Key West (Island) by bus

Calendar14Weekly Buses
Duration34h 25mAverage Duration
Ticket$157Cheapest Price
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Questions & Answers

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

American Airlines, United Airlines, and two other airlines 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 34h 25m.

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