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

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There are 6 ways to get from Wallkill 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 Midway International Airport

    best
    1. Take the train from Beacon to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    6h 37m
    $176–611

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

    cheapest
    1. Take the bus from Newburgh to White Plains, Nybus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    7h 36m
    $133–412

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 33m
    $203–420

  4. Bus

    1. Take the bus from Newburgh ShortLine Transportation Center to Port Authority Bus Terminalbus bus ShortLine Hudson
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus FlixBus N2640
    23h 41m
    $167–271

  5. Drive 792.2 mi

    1. Drive from Wallkill to Chicagocar car 792.2 mi
    13h 6m
    $145–209

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

    1. Take the train from Beacon to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    6h 55m
    $141–371

Laguardia Airport (LGA) to Chicago Midway International Airport (MDW) flights

Calendar68Weekly Planes
Duration2h 55mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

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

Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $110–310 and the journey takes 18h 2m. Alternatively, you can take a vehicle from Wallkill to Chicago Bus Station via Newburgh ShortLine Transportation Center, Port Authority Bus Terminal, 9 Av/W 40 St, W 34 St/7 Av, and New York Midtown in around 23h 41m.

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