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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)planeEYW - ORD
    6h 56m
    $209–694

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

    cheapest
    1. Fly from Key West International Airport (EYW) to Chicago Midway International Airport (MDW)planeEYW - MDW
    8h 5m
    $179–644

  3. Bus

    1. Take the bus from Big Pine Key to Miami Airport Stationbus
    2. Take the bus from Miami Airport Station to Atlanta Bus Stationbus
    3. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus
    36h 22m
    $182–499

  4. Bus, train

    1. Take the bus from Big Pine Key to Miami Airport StationbusGreyhound US0720s
    2. Take the train from Hollywood Amtrak Station to Chicago Union StationtrainFloridian
    2d 5h
    $255–825

  5. Drive 1,457.5 mi

    1. Drive from Florida Keys to Chicagocar1,457.5 mi
    26h 19m
    $266–385

  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
    2. Fly from Miami International Airport (MIA) to Chicago O'Hare International Airport (ORD)planeMIA - ORD
    9h 42m
    $189–499

  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
    2. Fly from Miami International Airport (MIA) to Chicago Midway International Airport (MDW)planeMIA - MDW
    9h 29m
    $209–559

  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
    2. Fly from Fort Lauderdale–Hollywood International Airport (FLL) to Chicago Midway International Airport (MDW)planeFLL - MDW
    9h 49m
    $224–549

Florida Keys to Chicago by foot and bus

Calendar8Weekly Services
Duration36h 22mAverage Duration
Ticket$182Cheapest 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 3 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 22m.

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