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

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There are 9 ways to get from White Plains to Chicago by plane, train (Amtrak), bus (Flixbus), car, train, bus, 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 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
    4h 59m
    $105–608

  2. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 50m
    $509–814

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    22h 55m
    $144–236

  4. Drive  808.6 mi

    1. Drive from White Plains to Chicagocar car 808.6 mi
    13h 29m
    $148–214

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

    1. Take the train from White Plains 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 19m
    $213–676

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

    1. Take the train from White Plains 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 36m
    $143–576

  7. Bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Grand Central to Terminal Bbus bus
    2. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 31m
    $156–894

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

    1. Take the train from White Plains to Grand Central Terminaltrain train
    2. Take the train from Grand Central Terminal to Jamaicatrain train
    3. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)plane plane JFK - ORD
    6h 10m
    $335–887

  9. Bus via Baltimore (Greyhound)

    1. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus bus Greyhound US0670 / ...
    2. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus Greyhound US0164
    25h 29m
    $167–272

White Plains to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 50mAverage Duration
Ticket$509Cheapest Price
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Comparing Your Travel Options

Map of how to get from White Plains to Chicago.ExpandLaunch map view
  • Distance: 768.4 mi
  • Duration: 4h 59m

What companies run services between White Plains, NY, USA and Chicago, IL, USA?

American Airlines and Delta fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $500–800 and the journey takes 18h 46m.

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