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How to get fromChicago Midway Airport (MDW) to Florida Keysby plane, train, bus, car, shuttle, or ferry

Find Transport to Florida Keys

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There are 7 ways to get from Chicago Midway Airport (MDW) to Florida Keys by plane, train, bus, car, shuttle, or ferry

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 Chicago Midway International Airport to Key West International Airport

    best
    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)plane plane MDW - EYW
    8h 6m
    $191–595

  2. Fly Chicago O'Hare International Airport to Key West International Airport

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    8h 28m
    $172–504

  3. Train, bus

    1. Take the train from Chicago Union Station to Miami Amtrak Stationtrain train Floridian
    2. Take the bus from Miami Airport Station to Big Pine Keybus bus Greyhound US0720s
    2d 6h
    $696–1,476

  4. Drive 1,453.4 mi

    1. Drive from Chicago Midway Airport (MDW) to Florida Keyscar car 1,453.4 mi
    26h 49m
    $266–384

  5. Fly Chicago Midway International Airport to Fort Lauderdale–Hollywood International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Fort Lauderdale–Hollywood International Airport (FLL)plane plane MDW - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FLshuttle bus
    8h 50m
    $307–807

  6. Fly Chicago Midway International Airport to Miami International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)plane plane MDW - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle bus
    8h 30m
    $283–768

  7. Fly Chicago Midway International Airport to Ft. Myers, ferry

    1. Fly from Chicago Midway International Airport (MDW) to Ft. Myers (RSW)plane plane MDW - RSW
    2. Take the ferry from Fort Myers Beach, FL to Key West, FLferry ferry
    11h 14m
    $305–807

Chicago Midway Airport (MDW) to Florida Keys by subway, bus, train, taxi, and foot

Calendar7Weekly Services
Duration2d 6hAverage Duration
Ticket$696Cheapest Price
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Questions & Answers

Map of how to get from Chicago Midway Airport (MDW) to Florida Keys.ExpandLaunch map view
  • Distance: 1,260.5 mi
  • Duration: 8h 6m

What companies run services between Chicago Midway Airport (MDW), USA and Florida Keys, 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.

Airlines
Train operators
Bus operators
Ferry operators

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