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

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There are 8 ways to get from Boston to Woodstock by plane, train, train (Amtrak), bus, 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. Fly Boston Logan Airport to Chicago O'Hare International Airport, train

    best
    1. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane plane BOS - ORD
    2. Take the train from Irving Park to Woodstocktrain train
    5h 31m
    $627–1,012

  2. Fly Boston Logan Airport to Chicago Midway International Airport, train

    cheapest
    1. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane plane BOS - MDW
    2. Take the train from Chicago OTC to Woodstocktrain train
    5h 58m
    $93–422

  3. Train

    1. Take the train from Boston to Chicago Union Stationtrain train Lake Shore Limited
    2. Take the train from Chicago OTC to Woodstocktrain train Up-Nw
    25h 10m
    $334–676

  4. Bus, train

    1. Take the bus from Boston to New York Midtownbus bus
    2. Take the bus from New York Midtown to Chicago Bus Stationbus bus
    3. Take the train from Chicago OTC to Woodstocktrain train
    25h 10m
    $183–307

  5. Drive 1,035.5 mi

    1. Drive from Boston to Woodstockcar car 1,035.5 mi
    18h 1m
    $189–273

  6. Fly Boston Logan Airport to General Mitchell International Airport, bus, train

    1. Fly from Boston Logan Airport (BOS) to General Mitchell International Airport (MKE)plane plane BOS - MKE
    2. Take the bus from Mitchell Airport to O'Hare International Airport - Terminal 2 Departuresbus bus
    3. Take the train from Irving Park to Woodstocktrain train
    7h 30m
    $702–1,879

  7. Bus to Manchester Airport, fly to Chicago Midway International Airport, train

    1. Take the bus from Boston to Boston Manchester Airportbus bus
    2. Fly from Manchester Airport (MHT) to Chicago Midway International Airport (MDW)plane plane MHT - MDW
    3. Take the train from Chicago OTC to Woodstocktrain train
    7h 53m
    $111–497

  8. Train to Theodore Francis Green State Airport, fly to Chicago Midway International Airport, train

    1. Take the train from South Station to TF Green Airporttrain train
    2. Fly from Theodore Francis Green State Airport (PVD) to Chicago Midway International Airport (MDW)plane plane PVD - MDW
    3. Take the train from Chicago OTC to Woodstocktrain train
    8h 30m
    $93–419

Boston to Woodstock by train and bus

Calendar7Weekly Services
Duration25h 10mAverage Duration
Ticket$334Cheapest Price
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Questions & Answers

Map of how to get from Boston to Woodstock.ExpandLaunch map view
  • Distance: 918.6 mi
  • Duration: 5h 31m

What companies run services between Boston, MA, USA and Woodstock, IL, USA?

You can take a train from Boston to Woodstock via Chicago Union Station, Clinton & Quincy, Washington & Canal, and Chicago OTC in around 25h 10m.

Airlines
Train operators
Bus operators

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