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How to get fromChicago to Florida Keysby plane, bus (Flixbus, Greyhound), 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 (Flixbus, Greyhound), 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)planeORD - EYW
    7h 59m
    $190–674

  2. Bus

    cheapest
    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
    35h 35m
    $168–459

  3. Train, bus

    1. Take the train from Chicago Union Station to Hollywood Amtrak StationtrainFloridian
    2. Take the bus from Miami Airport Station to Big Pine KeybusGreyhound US0720s
    2d 5h
    $424–2,462

  4. Drive 1,452.8 mi

    1. Drive from Chicago to Florida Keyscar1,452.8 mi
    26h 27m
    $266–383

  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)planeMDW - EYW
    9h 10m
    $180–724

  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)planeORD - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle
    10h 33m
    $190–499

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

    1. Fly from Chicago Midway International Airport (MDW) to Miami International Airport (MIA)planeMDW - MIA
    2. Take a shuttle bus from Miami, FL - International Airport to Big Pine Key, FLshuttle
    10h 1m
    $220–599

  8. 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)planeMDW - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FLshuttle
    10h 26m
    $230–569

Chicago to Florida Keys by bus and foot

Calendar8Weekly Services
Duration35h 35mAverage Duration
Ticket$168Cheapest Price
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Questions & Answers

What companies run services between Chicago, IL, USA and Florida Keys, 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 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 35h 35m.

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