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How to get fromChicago to Woodstockby plane, bus, train, taxi, bus (Flixbus, Greyhound), car, or shuttle

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There are 10 ways to get from Chicago to Woodstock by plane, bus, train, taxi, bus (Flixbus, Greyhound), car, or shuttle

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 Manchester Airport, bus

    best
    1. Fly from Chicago Midway International Airport (MDW) to Manchester Airport (MHT)plane plane MDW - MHT
    2. Take the bus from Boston Manchester Airport to White River Junction Bus Stationbus bus
    7h 8m
    $200–691

  2. Drive 897.9 mi

    cheapest
    1. Drive from Chicago to Woodstockcar car 897.9 mi
    16h 16m
    $164–237

  3. Train, taxi (Amtrak)

    1. Take the train from Chicago Union Station to Schenectadytrain train
    2. Take the train from Schenectady to Rutlandtrain train
    3. Take the taxi from Rutland to Woodstocktaxi taxi
    19h 51m
    $341–653

  4. Bus

    1. Take the bus from Chicago Bus Station to Newark Penn Stationbus bus
    2. Take the bus from Newark Penn Station to Port Authority Bus Terminalbus bus 108
    3. Take the bus from New York, NY to Dartmouth Collegebus bus
    23h 40m
    $328–502

  5. Fly Chicago O'Hare International Airport to Manchester Airport, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Manchester Airport (MHT)plane plane ORD - MHT
    2. Take the bus from Boston Manchester Airport to White River Junction Bus Stationbus bus
    7h 41m
    $186–561

  6. Fly Chicago Midway International Airport to Boston Logan Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Boston Logan Airport (BOS)plane plane MDW - BOS
    2. Take a shuttle bus from Boston Logan Airport Terminal C to Killington Ski Resortshuttle bus
    7h 28m
    $212–625

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

    1. Fly from Chicago O'Hare International Airport (ORD) to Burlington International Airport (BTV)plane plane ORD - BTV
    2. Take the bus from Burlington Downtown Transit Ctr to White River Junction Bus Stationbus bus
    8h 10m
    $202–693

  8. Fly Chicago Midway International Airport to Bradley International Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Bradley International Airport (BDL)plane plane MDW - BDL
    2. Take the train from Windsor Locks to Windsor Stationtrain train
    9h
    $228–713

  9. Fly Chicago Midway International Airport to Albany County Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Albany County Airport (ALB)plane plane MDW - ALB
    2. Take the train from Schenectady to Rutlandtrain train
    9h 57m
    $208–864

  10. Fly Chicago O'Hare International Airport to Albany County Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Albany County Airport (ALB)plane plane ORD - ALB
    2. Take the train from Schenectady to Rutlandtrain train
    10h 24m
    $178–714

Chicago Midway International Airport (MDW) to Manchester Airport (MHT) flights

Calendar27Weekly Planes
Duration3h 23mAverage Duration
Ticket$107Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Woodstock.ExpandLaunch map view
  • Distance: 950.4 mi
  • Duration: 7h 8m

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

You can take a bus from Chicago Bus Station to Woodstock via Newark Penn Station, Port Authority Bus Terminal, West 42nd Street & 8th Avenue, New York, NY, and Dartmouth College in around 23h 40m.

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