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How to get fromChicago Station (CTA Logan Square branch) to Florida Keysby plane, bus (Greyhound), train, bus, car or shuttle

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There are 8 ways to get from Chicago Station (CTA Logan Square branch) to Florida Keys by plane, bus (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
    8h 3m
    $132–479

  2. Bus (Greyhound)

    1. Take the bus from Chicago Train 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
    39h 14m
    $171–358

  3. Train, bus

    1. Take the train from Chicago Union Station to Miami Amtrak StationtrainFloridian
    2. Take the bus from Miami Airport Station to Big Pine KeybusGreyhound US0720s
    2d 6h
    $270–617

  4. Drive 1,455.6 mi

    1. Drive from Chicago Station (CTA Logan Square branch) to Florida Keyscar1,455.6 mi
    26h 30m
    $266–384

  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 26m
    $161–676

  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 23m
    $186–484

  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)planeMDW - FLL
    2. Take a shuttle bus from Fort Lauderdale, FL - International Airport to Big Pine Key, FLshuttle
    10h 52m
    $231–591

  8. 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 27m
    $236–691

Chicago Station (CTA Logan Square branch) to Florida Keys by bus and foot (Greyhound)

Calendar14Weekly Services
Duration39h 14mAverage Duration
Ticket$171Cheapest Price
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Questions & Answers

What companies run services between Chicago Station (CTA Logan Square branch), 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 & Paulina to Florida Keys via Chicago & Michigan, Michigan & Superior, Union Station Transit Center, Chicago Train Station, Atlanta Bus Station, Miami Airport Station, Big Pine Key, Big Pine Key - CVS / MM30, and Sugarloaf Key - Lower - Sugarloaf Lodge in around 39h 14m.

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