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

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

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 to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Kingston to Albanybus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 13m
    $138–677

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

    cheapest
    1. Take the bus from Kingston to Albanybus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    7h 42m
    $118–567

  3. Bus, train

    1. Take the bus from Woodstock to Uticabus bus Adt P704
    2. Take the train from Utica Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    19h 22m
    $247–558

  4. Bus

    1. Take the bus from Kingston 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
    21h
    $156–348

  5. Drive 822.5 mi

    1. Drive from Woodstock to Chicagocar car 822.5 mi
    14h
    $151–217

  6. Bus to Laguardia Airport, fly to Chicago Midway International Airport

    1. Take the bus from Kingston to New Yorkbus bus
    2. Fly from Laguardia Airport (LGA) to Chicago Midway International Airport (MDW)plane plane LGA - MDW
    7h 50m
    $237–664

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

    1. Take the bus from Kingston, 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 38m
    $126–636

  8. Train (Amtrak)

    1. Take the train from Poughkeepsie Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    21h 6m
    $270–600

Woodstock to Chicago by bus and train

Calendar11Weekly Services
Duration19h 22mAverage Duration
Ticket$247Cheapest Price
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Questions & Answers

Map of how to get from Woodstock to Chicago.ExpandLaunch map view
  • Distance: 801.5 mi
  • Duration: 7h 13m

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

You can take a bus from Woodstock to Chicago Bus Station via Kingston, New York, Port Authority Bus Terminal, and Newark Penn Station in around 21h. Alternatively, Amtrak operates a train from Poughkeepsie Amtrak Station to Chicago Union Station once daily. Tickets cost $270–600 and the journey takes 18h 2m.

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