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

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There are 6 ways to get from Key West to Chicago by plane, bus (Greyhound, Flixbus), bus, train, or car

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)planeEYW - ORD
    4h 26m
    $154–619

  2. Fly to Chicago Midway International Airport

    cheapest
    1. Fly from Key West International Airport (EYW) to Chicago Midway International Airport (MDW)planeEYW - MDW
    5h 35m
    $124–569

  3. Bus

    1. Take the bus from N Roosevelt & 3rd Street to Big Pine Key - Auto Store / NAPA MM30busLks
    2. Take the bus from Big Pine Key to Miami Airport Stationbus
    3. Take the bus from Miami Airport Station to Atlanta Bus Stationbus
    4. Take the bus from Atlanta Bus Station to Chicago Bus Stationbus
    36h 51m
    $179–466

  4. Bus, train

    1. Take the bus from N Roosevelt & 4th Street to Big Pine Key - Auto Store / NAPA MM30busLks
    2. Take the bus from Big Pine Key to Miami Airport Stationbus
    3. Take the train from Hollywood Amtrak Station to Chicago Union Stationtrain
    2d 5h
    $252–792

  5. Drive 1,472.9 mi

    1. Drive from Key West to Chicagocar1,472.9 mi
    26h 41m
    $269–389

  6. Fly to South Bend, train

    1. Fly from Key West International Airport (EYW) to South Bend (SBN)planeEYW - SBN
    2. Take the train from South Bend Airport to Van Buren St.train
    8h 21m
    $165–729

Key West to Chicago by bus and foot

Calendar8Weekly Services
Duration36h 51mAverage Duration
Ticket$179Cheapest Price
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Questions & Answers

What companies run services between Key West, 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 N Roosevelt & 3rd Street to Chicago Bus Station via Big Pine Key - Auto Store / NAPA MM30, Big Pine Key, Miami Airport Station, and Atlanta Bus Station in around 36h 51m.

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