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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 9 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 18m
    $195–579

  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 17m
    $102–469

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 18m
    $308–662

  4. Bus

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 33m
    $197–280

  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 39m
    $225–679

  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 7m
    $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 34m
    $198–897

  9. Train, bus

    1. Take the train from Chappaqua to Grand Central Terminaltrain train
    2. Take the bus from Port Authority Bus Terminal to Baltimorebus bus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus bus
    25h
    $209–330

Westchester County to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 18mAverage Duration
Ticket$308Cheapest Price
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Questions & Answers

Map of how to get from Westchester County to Chicago.ExpandLaunch map view
  • Distance: 769.3 mi
  • Duration: 5h 18m

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 $300–650 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $140–240 and the journey takes 16h 55m. Jefferson Lines also services this route once daily.

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