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How to get fromChicago to Chappaquaby plane, train, train (Amtrak), bus (Flixbus), car or bus

Find Transport to Chappaqua

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There are 9 ways to get from Chicago to Chappaqua by plane, train, 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. Fly Chicago Midway International Airport to Laguardia Airport, train

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 20m
    $100–508

  2. Fly Chicago O'Hare International Airport to Laguardia Airport, train

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Laguardia Airport (LGA)plane plane ORD - LGA
    2. Take the train from 125th Street - Harlem to Chappaquatrain train
    5h 42m
    $64–308

  3. Train (Amtrak)

    1. Take the train from Chicago Union Station to Croton-Harmon Amtrak Stationtrain train Lake Shore Limited
    21h 10m
    $260–555

  4. Bus (Flixbus)

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2640
    22h 54m
    $133–229

  5. Drive 812.6 mi

    1. Drive from Chicago to Chappaquacar car 812.6 mi
    13h 42m
    $149–215

  6. Fly Chicago O'Hare International Airport to John F. Kennedy International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to John F. Kennedy International Airport (JFK)plane plane ORD - JFK
    2. Take the train from Grand Central Terminal to Chappaquatrain train
    6h 2m
    $72–300

  7. Fly Chicago O'Hare International Airport to Newark Liberty International Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Newark Liberty International Airport (EWR)plane plane ORD - EWR
    2. Take the train from Grand Central Terminal to Chappaquatrain train
    6h 10m
    $86–323

  8. Fly Chicago O'Hare International Airport to Westchester County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the train from White Plains to Chappaquatrain train
    6h 13m
    $452–620

  9. Bus, train

    1. Take the bus from Chicago Bus Station to Baltimore Downtown Bus Stationbus bus
    2. Take the bus from Baltimore Downtown Bus Station to Port Authority Bus Terminalbus bus
    3. Take the train from Grand Central Terminal to Chappaquatrain train
    23h 4m
    $191–377

Chicago to Chappaqua by train and bus (Amtrak)

Calendar7Weekly Services
Duration21h 10mAverage Duration
Ticket$260Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Chicago Union Station to Croton-Harmon Amtrak Station once daily. Tickets cost $250–550 and the journey takes 19h 23m. Alternatively, Flixbus USA operates a bus from Chicago Bus Station to New York Midtown once daily. Tickets cost $120–220 and the journey takes 20h 10m.

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