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

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There are 9 ways to get from Woodstock to Chicago by bus, plane, taxi, train, bus (Greyhound, Flixbus), or car

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 Manchester Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from White River Junction Bus Station to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    5h 55m
    $200–606

  2. Drive 896.8 mi

    cheapest
    1. Drive from Woodstock to Chicagocar car 896.8 mi
    16h 14m
    $164–237

  3. Taxi, train (Amtrak)

    1. Take the taxi from Woodstock to Rutlandtaxi taxi
    2. Take the train from Rutland to Schenectadytrain train
    3. Take the train from Schenectady to Chicago Union Stationtrain train
    19h 38m
    $339–678

  4. Bus

    1. Take the bus from Dartmouth College to New York, NYbus 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
    23h 59m
    $329–508

  5. Bus to Manchester Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from White River Junction Bus Station to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago O'Hare International Airport (ORD)plane plane MHT - ORD
    6h 30m
    $185–536

  6. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Windsor Station to Windsor Lockstrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    8h 5m
    $212–604

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

    1. Take the bus from White River Junction Bus Station to Burlington Downtown Transit Ctrbus bus
    2. Fly from Burlington International Airport (BTV) to Chicago O'Hare International Airport (ORD)plane plane BTV - ORD
    7h 48m
    $187–569

  8. Taxi, train, bus to Albany County Airport, fly to Chicago Midway International Airport

    1. Take the taxi from Woodstock to Rutlandtaxi taxi
    2. Take the train from Rutland to Saratoga Springs Amtrak Stationtrain train
    3. Take the bus from Saratoga Springs to Albanybus bus
    4. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    7h 50m
    $206–758

  9. Taxi, train, bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Woodstock to Rutlandtaxi taxi
    2. Take the train from Rutland to Saratoga Springs Amtrak Stationtrain train
    3. Take the bus from Saratoga Springs to Albanybus bus
    4. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    8h 19m
    $191–638

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

Calendar25Weekly Planes
Duration3h 29mAverage Duration
Ticket$95Cheapest Price
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Questions & Answers

Map of how to get from Woodstock to Chicago.ExpandLaunch map view
  • Distance: 947 mi
  • Duration: 5h 55m

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

You can take a vehicle from Woodstock to Chicago Bus Station via Dartmouth College, New York, NY, E 42 St/3 Av, West 42nd Street & 8th Avenue, Port Authority Bus Terminal, and Newark Penn Station in around 23h 59m.

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