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

Find Transport to Key West

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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)planeORD - EYW
    5h 13m
    $154–618

  2. Fly from Chicago Midway International Airport

    cheapest
    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)planeMDW - EYW
    6h 9m
    $144–668

  3. Bus

    1. Take the bus from Chicago Bus Station to Atlanta Bus Stationbus
    2. Take the bus from Atlanta Bus Station to Miami Airport Stationbus
    3. Take the bus from Miami Airport Station to Big Pine Keybus
    4. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd StreetbusLks
    36h 21m
    $168–459

  4. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak Stationtrain
    2. Take the bus from Miami Airport Station to Big Pine Keybus
    3. Take the bus from Big Pine Key - CVS / MM30 to N Roosevelt & 3rd StreetbusLks
    2d 6h
    $424–2,462

  5. Drive 1,468.2 mi

    1. Drive from Chicago to Key Westcar1,468.2 mi
    26h 49m
    $268–387

  6. Train to South Bend, fly

    1. Take the train from Van Buren St. to South Bend Airporttrain
    2. Fly from South Bend (SBN) to Key West International Airport (EYW)planeSBN - EYW
    7h 47m
    $204–877

  7. Train to General Mitchell International Airport, fly

    1. Take the train from Chicago Union Station to Milwaukeetrain
    2. Fly from General Mitchell International Airport (MKE) to Key West International Airport (EYW)planeMKE - EYW
    8h 42m
    $235–1,082

Chicago to Key West by bus and foot

Calendar8Weekly Services
Duration36h 21mAverage Duration
Ticket$168Cheapest 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 3 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 36h 21m.

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