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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 10 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 O'Hare International Airport

    best
    1. Take the train from Chappaqua to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    5h 43m
    $70–288

  2. Train (Amtrak)

    1. Take the train from Croton-Harmon Amtrak Station to Chicago Union StationtrainLake Shore Limited
    20h 39m
    $139–383

  3. Bus (Flixbus)

    1. Take the bus from New York Midtown to Chicago Bus StationbusFlixBus N2640
    23h 44m
    $112–254

  4. Drive 811.9 mi

    1. Drive from Chappaqua to Chicagocar811.9 mi
    13h 29m
    $149–214

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

    1. Take the train from Chappaqua to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    5h 32m
    $95–448

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

    1. Take the train from Chappaqua to Grand Central Terminaltrain
    2. Fly from John F. Kennedy International Airport (JFK) to Chicago O'Hare International Airport (ORD)planeJFK - ORD
    6h 14m
    $826–1,040

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

    1. Take the train from Chappaqua to Grand Central Terminaltrain
    2. Take the bus from Bryant Park to Terminal Bbus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)planeEWR - ORD
    6h 38m

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

    1. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    6h 26m
    $77–380

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

    1. Take the train from Chappaqua to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to General Mitchell International Airport (MKE)planeLGA - MKE
    3. Take the train from Milwaukee to Chicago Union Stationtrain
    8h 5m
    $207–628

  10. Train, bus

    1. Take the train from Chappaqua to Grand Central Terminaltrain
    2. Take the bus from Port Authority Bus Terminal to Baltimore Downtown Bus Stationbus
    3. Take the bus from Baltimore Downtown Bus Station to Chicago Bus Stationbus
    24h 43m
    $123–349

Chappaqua to Chicago by bus and train (Amtrak)

Calendar7Weekly Services
Duration20h 39mAverage Duration
Ticket$139Cheapest Price
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Questions & Answers

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 $130–370 and the journey takes 18h 46m. Alternatively, Flixbus USA operates a bus from New York Midtown to Chicago Bus Station once daily. Tickets cost $95–230 and the journey takes 20h 25m.

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