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How to get fromGreenwich to Chicagoby plane, train (Amtrak), bus (Greyhound, Flixbus), car, train, or bus

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There are 9 ways to get from Greenwich to Chicago by plane, train (Amtrak), bus (Greyhound, Flixbus), car, train, or bus

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 Westchester County Airport to Chicago O'Hare International Airport

    best
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    3h 43m
    $133–629

  2. Train

    1. Take the train from 125th Street - Harlem to Croton-Harmontrain train Hudson
    2. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    21h 48m
    $520–832

  3. Bus

    1. Take the bus from Stamford Bus Stop to Port Authority Bus Terminalbus bus Greyhound US0240
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 47m
    $159–253

  4. Drive  813.1 mi

    1. Drive from Greenwich to Chicagocar car 813.1 mi
    13h 36m
    $149–215

  5. Train, bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the train from Greenwich to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 26m
    $215–678

  6. Train, bus to Laguardia Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenwich to 125th Street - Harlemtrain train
    2. Take the bus from E 125 St/Lexington Av to Laguardia Rd/94 Stbus bus
    3. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 48m
    $145–578

  7. Train to John F. Kennedy International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 15m
    $336–889

  8. Train, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Take the bus from Grand Central to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 44m
    $147–796

  9. Train, bus

    1. Take the train from Greenwich to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h 34m
    $183–289

Greenwich to Chicago by train

Calendar7Weekly Trains
Duration21h 48mAverage Duration
Ticket$520Cheapest Price
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Comparing Your Travel Options

Map of how to get from Greenwich to Chicago.ExpandLaunch map view
  • Distance: 761.1 mi
  • Duration: 3h 43m

What companies run services between Greenwich, CT, USA and Chicago, IL, USA?

American Airlines and Delta fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a train from Greenwich to Chicago Union Station via 125th Street - Harlem and Croton-Harmon Amtrak Station in around 21h 48m.

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Want to know more about travelling around United States

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