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

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There are 8 ways to get from Pawling to Chicago by train, plane, 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. Train to Laguardia Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Southeast to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)planeLGA - ORD
    6h 55m
    $76–305

  2. Bus, train

    1. Take the bus from Chamber of Commerce to Poughkeepsie Train StationbusE
    2. Take the train from Poughkeepsie Amtrak Station to Chicago Union StationtrainLake Shore Limited
    20h 6m
    $77–342

  3. Bus

    1. Take the bus from Chamber of Commerce to Poughkeepsie Train StationbusE
    2. Take the bus from Metro North Station to TransCenterbusWpp
    3. Take the bus from New York Midtown to Chicago Bus Stationbus
    27h 15m
    $102–244

  4. Drive 822.8 mi

    1. Drive from Pawling to Chicagocar822.8 mi
    13h 34m
    $151–217

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

    1. Take the train from Southeast to 125th Street - Harlemtrain
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)planeLGA - MDW
    6h 44m
    $101–475

  6. Train to Westchester County Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Southeast to White Plainstrain
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)planeHPN - ORD
    7h 39m
    $89–397

  7. Bus, train to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the bus from Chamber of Commerce to Poughkeepsie Train Stationbus
    2. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)planeALB - MDW
    8h 46m
    $122–645

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

    1. Take the train from Southeast 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
    9h 17m
    $218–640

Pawling to Chicago by bus and train

Calendar7Weekly Services
Duration20h 6mAverage Duration
Ticket$77Cheapest Price
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Questions & Answers

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

You can take a bus from Chamber of Commerce to Chicago Bus Station via Metro North Station, TransCenter, White Plains Bus Station, and New York Midtown in around 27h 15m.

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