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

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There are 7 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 Midway International Airport

    best
    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 25m
    $116–525

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

    cheapest
    1. Take the train from Southeast to White Plainstrain train
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 21m
    $99–437

  3. Bus, train

    1. Take the bus from Chamber of Commerce to Poughkeepsie Train Stationbus bus E
    2. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    20h 6m
    $282–602

  4. Bus

    1. Take the bus from Chamber of Commerce to Poughkeepsie Train Stationbus bus E
    2. Take the bus from Newburgh ShortLine Transportation Center to 9th Ave & W 30th Stbus bus
    3. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    28h 33m
    $166–306

  5. Drive 822.8 mi

    1. Drive from Pawling to Chicagocar car 822.8 mi
    13h 43m
    $151–217

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

    1. Take the train from Southeast to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 40m
    $121–285

  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 bus
    2. Take the train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Stationtrain train
    3. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 33m
    $133–820

Pawling to Chicago by bus and train

Calendar7Weekly Services
Duration20h 6mAverage Duration
Ticket$282Cheapest Price
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Questions & Answers

Map of how to get from Pawling to Chicago.ExpandLaunch map view
  • Distance: 800.8 mi
  • Duration: 6h 25m

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 Poughkeepsie Train Station, Poughkeepsie, Beacon, Beacon Station, Newburgh ShortLine Transportation Center, 9th Ave & W 30th St, and New York Midtown in around 28h 33m.

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