Rome2Rio

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

Find Transport to Chicago

See all options

There are 10 ways to get from Wallkill to Chicago by bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Bus, bus to Newark Liberty International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Rosendale to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Terminal Bbus bus
    3. Fly from Newark Liberty International Airport (EWR) to Chicago O'Hare International Airport (ORD)plane plane EWR - ORD
    8h 39m

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

    cheapest
    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago O'Hare International Airport (ORD)plane plane LGA - ORD
    9h 8m
    $71–318

  3. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 33m
    $168–450

  4. Bus

    1. Take the bus from Rosendale to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    24h 51m
    $119–305

  5. Drive 792.2 mi

    1. Drive from Wallkill to Chicagocar car 792.2 mi
    12h 58m
    $145–209

  6. Bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the bus from Rosendale, Ny to Albany Sunybus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    8h 4m
    $124–599

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

    1. Take the train from Poughkeepsie to 125th Street - Harlemtrain train
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    9h 2m
    $101–488

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

    1. Take the bus from Rosendale, Ny to White Plains, Nybus bus
    2. Fly from Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD)plane plane HPN - ORD
    9h 34m
    $89–403

  9. Bus, bus to Lehigh Valley International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Rosendale to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Lehigh Valley International Airport Trans Bridge Bus Stopbus bus
    3. Fly from Lehigh Valley International Airport (ABE) to Chicago O'Hare International Airport (ORD)plane plane ABE - ORD
    11h 51m
    $149–450

  10. Bus, bus to Wilkes-Barre/Scranton International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Rosendale to New Yorkbus bus
    2. Take the bus from Port Authority Bus Terminal to Scranton, PAbus bus
    3. Fly from Wilkes-Barre/Scranton International Airport (AVP) to Chicago O'Hare International Airport (ORD)plane plane AVP - ORD
    11h 23m
    $160–615

Wallkill to Chicago by bus

Calendar7Weekly Buses
Duration24h 51mAverage Duration
Ticket$119Cheapest Price
See schedules

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 $75–340 and the journey takes 18h 2m. Alternatively, you can take a bus from Wallkill Popp Park to Chicago Bus Station via Rosendale, New York, Port Authority Bus Terminal, and Newark Penn Station in around 24h 51m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Where to next?

Trips from Wallkill

Trips to Chicago

Popular routes