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

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There are 8 ways to get from Chicago to Pawling by plane, train, bus, bus (Flixbus), or car

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 Pawlingtrain train
    6h 44m
    $94–436

  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 Pawlingtrain train
    7h 5m
    $70–316

  3. Train, bus

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    2. Take the bus from Poughkeepsie Train Station to Chamber of Commercebus bus E
    20h 41m
    $170–343

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus
    2. Take the bus from TransCenter to Metro North Stationbus bus Wpp
    3. Take the bus from Poughkeepsie Train Station to Chamber of Commercebus bus E
    27h 1m
    $111–275

  5. Drive 822.3 mi

    1. Drive from Chicago to Pawlingcar car 822.3 mi
    13h 39m
    $151–217

  6. 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 Pawlingtrain train
    7h 37m
    $92–361

  7. 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 Pawlingtrain train
    7h 37m
    $102–478

  8. Fly Chicago Midway International Airport to Albany County Airport, train, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Albany-Rensselaer Amtrak Station to Poughkeepsie Amtrak Stationtrain train
    3. Take the bus from Poughkeepsie Train Station to Chamber of Commercebus bus
    9h
    $142–795

Chicago to Pawling by train and bus

Calendar7Weekly Services
Duration20h 41mAverage Duration
Ticket$170Cheapest Price
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Questions & Answers

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

You can take a bus from Chicago Bus Station to Chamber of Commerce via New York Midtown, White Plains Bus Station, TransCenter, and Poughkeepsie Train Station in around 27h 1m.

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