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How to get fromFlorida Keys to Chicagoby plane, bus (Greyhound, Flixbus), bus, train, car or shuttle

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There are 8 ways to get from Florida Keys to Chicago by plane, bus (Greyhound, Flixbus), bus, train, 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 Key West International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Key West International Airport (EYW) to Chicago O'Hare International Airport (ORD)plane plane EYW - ORD
    7h 10m
    $224–599

  2. Bus

    cheapest
    1. Take the bus from Big Pine Key to Miami Airport Stationbus bus
    2. Take the bus from Miami Airport Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus bus
    36h 23m
    $198–494

  3. Bus, train

    1. Take the bus from Big Pine Key to Miami Airport Stationbus bus Greyhound US0720s
    2. Take the train from Hollywood Amtrak Station to Chicago Union Stationtrain train Floridian
    2d 5h
    $576–1,350

  4. Drive 1,457.5 mi

    1. Drive from Florida Keys to Chicagocar car 1,457.5 mi
    26h 36m
    $266–385

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

    1. Fly from Key West International Airport (EYW) to Chicago Midway International Airport (MDW)plane plane EYW - MDW
    8h 43m
    $234–819

  6. Shuttle to Miami International Airport, fly to Chicago O'Hare International Airport

    1. Take a shuttle bus from Big Pine Key, FL to Miami, FL - International Airportshuttle bus
    2. Fly from Miami International Airport (MIA) to Chicago O'Hare International Airport (ORD)plane plane MIA - ORD
    9h 45m
    $204–509

  7. Shuttle to Miami International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Big Pine Key, FL to Miami, FL - International Airportshuttle bus
    2. Fly from Miami International Airport (MIA) to Chicago Midway International Airport (MDW)plane plane MIA - MDW
    9h 24m
    $264–739

  8. Shuttle to Fort Lauderdale–Hollywood International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Big Pine Key, FL to Fort Lauderdale, FL - International Airportshuttle bus
    2. Fly from Fort Lauderdale–Hollywood International Airport (FLL) to Chicago Midway International Airport (MDW)plane plane FLL - MDW
    9h 54m
    $269–659

Florida Keys to Chicago by foot and bus

Calendar14Weekly Services
Duration36h 23mAverage Duration
Ticket$198Cheapest Price
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Questions & Answers

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

American Airlines, United Airlines, and Delta fly from Key West International Airport (EYW) to Chicago O'Hare International Airport (ORD) every 4 hours. Alternatively, you can take a vehicle from Florida Keys to Chicago Bus Station via Sugarloaf Key - Lower - Opposite Sugarloaf Lodge, Big Pine Key - Auto Store / NAPA MM30, Big Pine Key, Miami Airport Station, and Atlanta Bus Station in around 36h 23m.

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