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

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There are 9 ways to get from Chappaqua 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 26m
    $145–578

  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 19m
    $92–440

  3. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 39m
    $309–613

  4. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2641 / ...
    20h 44m
    $140–238

  5. Drive 811.9 mi

    1. Drive from Chappaqua to Chicagocar car 811.9 mi
    13h 38m
    $149–214

  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 42m
    $100–498

  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 11m
    $417–890

  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 41m
    $138–697

  9. 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
    24h 44m
    $168–354

Chappaqua to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 39mAverage Duration
Ticket$309Cheapest Price
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Questions & Answers

Map of how to get from Chappaqua to Chicago.ExpandLaunch map view
  • Distance: 769.3 mi
  • Duration: 5h 26m

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

Amtrak operates a train from Croton-Harmon Amtrak Station to Chicago Union Station once daily. Tickets cost $300–600 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station twice daily. Tickets cost $130–220 and the journey takes 16h 55m.

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