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How to get fromWestchester County to Chicagoby train, plane, train (Amtrak), bus (Flixbus), car, or bus

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There are 10 ways to get from Westchester County to Chicago by train, plane, train (Amtrak), bus (Flixbus), car, 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. Train to Laguardia Airport, fly to Chicago Midway International Airport

    best
    1. Take the train from Chappaqua to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    5h 21m
    $215–679

  2. Fly Westchester County Airport to Chicago O'Hare International Airport

    cheapest
    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    6h 23m
    $112–619

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 19m
    $508–812

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640 / ...
    24h 31m
    $146–239

  5. Drive  812.3 mi

    1. Drive from Westchester County to Chicagocar car 812.3 mi
    13h 41m
    $149–215

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

    1. Take the train from Chappaqua to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    5h 38m
    $145–579

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

    1. Take the train from Chappaqua 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
    $337–890

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

    1. Take the train from Chappaqua to Grand Central Terminaltrain train
    2. Take the bus from Bryant Park to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    6h 36m
    $158–897

  9. Train to Laguardia Airport, fly to General Mitchell International Airport, train

    1. Take the train from Chappaqua to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)plane plane LGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain train
    7h 55m
    $200–913

  10. Train, bus

    1. Take the train from Chappaqua 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
    $169–275

Westchester County to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 19mAverage Duration
Ticket$508Cheapest Price
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Comparing Your Travel Options

Map of how to get from Westchester County to Chicago.ExpandLaunch map view
  • Distance: 769.3 mi
  • Duration: 5h 21m

What companies run services between Westchester County, NY, USA and Chicago, IL, USA?

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. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–230 and the journey takes 20h 25m.

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