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

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There are 8 ways to get from Chicago Union Station 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 10m
    $170–509

  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
    35h 49m
    $252–485

  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
    $703–1,393

  4. Drive 1,453.6 mi

    1. Drive from Chicago Union Station to Florida Keyscar car 1,453.6 mi
    26h 44m
    $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)plane plane MDW - EYW
    9h 56m
    $190–649

  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 37m
    $314–939

  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 39m
    $304–859

  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 19m
    $284–789

Chicago Union Station to Florida Keys by foot and bus

Calendar24Weekly Services
Duration35h 49mAverage Duration
Ticket$252Cheapest Price
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Questions & Answers

Map of how to get from Chicago Union Station to Florida Keys.ExpandLaunch map view
  • Distance: 1,294.2 mi
  • Duration: 8h 10m

What companies run services between Chicago Union Station, 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) every 4 hours. Alternatively, you can take a vehicle from Chicago Union Station to Florida Keys via Chicago Bus Station, Atlanta Bus Station, Miami Airport Station, Big Pine Key, Big Pine Key - CVS / MM30, and Sugarloaf Key - Lower - Sugarloaf Lodge in around 35h 49m.

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