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How to get fromChicago to Key Westby plane, bus (Flixbus, Greyhound), train, bus or car

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There are 7 ways to get from Chicago to Key West by plane, bus (Flixbus, Greyhound), train, bus, 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 9m
    $134–618

  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 Big Pine Keybus bus
    4. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    35h 46m
    $160–351

  3. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain train
    2. Take the bus from Miami Airport Station to Big Pine Keybus bus
    3. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd Streetbus bus Lks
    2d 6h
    $335–618

  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 14m
    $174–818

  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 13m
    $214–977

  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 27m
    $245–1,229

Chicago to Key West by bus and foot

Calendar14Weekly Services
Duration35h 46mAverage Duration
Ticket$160Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Key West, 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 N Roosevelt & 3rd Street via Atlanta Bus Station, Miami Airport Station, Big Pine Key, and Big Pine Key - CVS / MM30 in around 35h 46m.

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