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How to get fromKey West (Island) to Chicagoby plane, bus (Greyhound, Flixbus), bus, train, car or bus (Greyhound)

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There are 7 ways to get from Key West (Island) to Chicago by plane, bus (Greyhound, Flixbus), bus, train, car, or bus (Greyhound)

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 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
    4h 26m
    $129–532

  2. Bus

    1. Take the bus from Key West Airport 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
    33h 50m
    $154–365

  3. Bus, train

    1. Take the bus from Key West Airport to Miami Airport Stationbus bus Greyhound US0720s
    2. Take the train from Hollywood Amtrak Station to Chicago Union Stationtrain train Floridian
    2d 4h
    $277–591

  4. Drive 1,472.9 mi

    1. Drive from Key West to Chicagocar car 1,472.9 mi
    26h 58m
    $269–389

  5. Fly to Chicago Midway International Airport

    1. Fly from Key West International Airport (EYW) to Chicago Midway International Airport (MDW)plane plane EYW - MDW
    6h 7m
    $145–673

  6. Fly to South Bend, train

    1. Fly from Key West International Airport (EYW) to South Bend (SBN)plane plane EYW - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    8h 37m
    $176–782

  7. Bus via Pembroke Pines (Greyhound)

    1. Take the bus from Key West Airport to Miami Airport Stationbus bus
    2. Take the bus from Hollywood Sheridan Trirail Station to Atlanta Bus Stationbus bus
    3. Take the bus from Atlanta Bus Station to Chicago Train Stationbus bus
    38h 47m
    $172–351

Key West (Island) to Chicago by bus

Calendar14Weekly Buses
Duration33h 50mAverage Duration
Ticket$154Cheapest Price
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Questions & Answers

What companies run services between Key West (Island), 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 bus from Key West Airport to Chicago Bus Station via Miami Airport Station and Atlanta Bus Station in around 33h 50m.

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