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How to get fromChicago to Woodstockby plane, bus, train, bus (Flixbus), car, or train (Amtrak)

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There are 9 ways to get from Chicago to Woodstock by plane, bus, train, bus (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. Fly Chicago Midway International Airport to Laguardia Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Laguardia Airport (LGA)plane plane MDW - LGA
    2. Take the bus from New York to Woodstockbus bus
    8h 6m
    $230–633

  2. Fly Chicago O'Hare International Airport to Westchester County Airport, bus

    cheapest
    1. Fly from Chicago O'Hare International Airport (ORD) to Westchester County Airport (HPN)plane plane ORD - HPN
    2. Take the bus from White Plains, Ny to Kingston, Nybus bus
    10h 10m
    $124–586

  3. Train, bus

    1. Take the train from Chicago Union Station to Utica Amtrak Stationtrain train Lake Shore Limited
    2. Take the bus from Utica to Woodstockbus bus Adt P707 / ...
    19h 19m
    $249–560

  4. Bus

    1. Take the bus from Chicago Bus Station to New York Midtownbus bus FlixBus N2641 / ...
    2. Take the bus from New York to Woodstockbus bus Adt P708 / ...
    21h 12m
    $162–301

  5. Drive 823.6 mi

    1. Drive from Chicago to Woodstockcar car 823.6 mi
    14h 3m
    $151–218

  6. Fly Chicago Midway International Airport to Albany County Airport, bus

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the bus from Albany to Kingstonbus bus
    7h 34m
    $156–823

  7. Fly Chicago O'Hare International Airport to Albany County Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the bus from Albany to Kingstonbus bus
    8h 1m
    $136–673

  8. Fly Chicago O'Hare International Airport to Wilkes-Barre/Scranton International Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Wilkes-Barre/Scranton International Airport (AVP)plane plane ORD - AVP
    2. Take the bus from Scranton to Port Authority Bus Terminalbus bus
    3. Take the bus from New York to Woodstockbus bus
    11h 20m
    $160–575

  9. Train (Amtrak)

    1. Take the train from Chicago Union Station to Poughkeepsie Amtrak Stationtrain train Lake Shore Limited
    22h 12m
    $272–570

Chicago to Woodstock by train and bus

Calendar11Weekly Services
Duration19h 19mAverage Duration
Ticket$249Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Woodstock.ExpandLaunch map view
  • Distance: 869.1 mi
  • Duration: 8h 6m

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

You can take a bus from Chicago Bus Station to Woodstock via New York Midtown, 8 Av/W 31 St, 8 Av/W 41 St, and New York in around 21h 12m. Alternatively, Amtrak operates a train from Chicago Union Station to Poughkeepsie Amtrak Station once daily. Tickets cost $270–600 and the journey takes 18h 43m.

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