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

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There are 5 ways to get from Chicago Midway Airport (MDW) to Key West by plane, bus (Greyhound, Flixbus), 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 Midway International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)plane plane MDW - EYW
    5h 20m
    $125–514

  2. Fly from Chicago O'Hare International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    5h 42m
    $106–423

  3. Bus

    1. Take the bus from Chicago Bus Station to Washington Union Stationbus bus
    2. Take the bus from Washington Union Station to Miamibus 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
    2d 1h
    $308–565

  4. Train, bus

    1. Take the train from Chicago Union Station to Miami 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 7h
    $696–1,476

  5. Drive 1,468.9 mi

    1. Drive from Chicago Midway Airport (MDW) to Key Westcar car 1,468.9 mi
    27h 12m
    $269–388

Chicago Midway Airport (MDW) to Key West by bus, foot, and taxi

Calendar8Weekly Services
Duration2d 1hAverage Duration
Ticket$308Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Key West.ExpandLaunch map view
  • Distance: 1,241.3 mi
  • Duration: 5h 20m

What companies run services between Chicago Midway Airport (MDW), USA and Key West, FL, USA?

Delta, Southwest Airlines, and Breeze Airways fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW) 3 times a day. Alternatively, you can take a bus from Midway CTA Station to N Roosevelt & 3rd Street via Austin/Jackson, Jackson & Austin Terminal, Jackson & Clinton, Chicago Bus Station, Washington Union Station, Miami, Miami Airport Station, Big Pine Key, and Big Pine Key - CVS / MM30 in around 2d 1h.

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