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How to get fromChicago to Florida Keysby plane, bus (Greyhound, Flixbus), train, bus, car, or shuttle

Find Transport to Florida Keys

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There are 8 ways to get from Chicago to Florida Keys by plane, bus (Greyhound, Flixbus), train, bus, car, or shuttle

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 O'Hare International Airport to Key West International Airport

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW)plane plane ORD - EYW
    8h
    $150–459

  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
    36h 45m
    $229–401

  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 Big Pine Keybus bus Greyhound US0720s
    2d 5h
    $1,152–1,773

  4. Drive  1,451.2 mi

    1. Drive from Chicago to Florida Keyscar car 1,451.2 mi
    26h 44m
    $265–383

  5. Fly Chicago Midway International Airport to Key West International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Key West International Airport (EYW)plane plane MDW - EYW
    9h 4m
    $180–599

  6. Fly Chicago O'Hare International Airport to Miami International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Miami International Airport (MIA)plane plane ORD - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle bus
    10h 23m
    $324–839

  7. 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
    10h 29m
    $324–579

  8. 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
    10h 14m
    $274–789

Chicago to Florida Keys by bus and foot

Calendar14Weekly Services
Duration36h 45mAverage Duration
Ticket$229Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Florida Keys.ExpandLaunch map view
  • Distance: 1,293.3 mi
  • Duration: 8h

What companies run services between Chicago, IL, USA and Florida Keys, FL, USA?

American Airlines, United Airlines, and Delta fly from Chicago O'Hare International Airport (ORD) to Key West International Airport (EYW) 5 times a day. Alternatively, you can take a bus from Chicago Bus Station to Florida Keys via Atlanta Bus Station, Miami Airport Station, Big Pine Key, Big Pine Key - CVS / MM30, and Sugarloaf Key - Lower - Sugarloaf Lodge in around 36h 45m.

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