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

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There are 11 ways to get from Woodstock to Chicago by train (Amtrak), bus, train, car, plane, bus (Flixbus, Greyhound), bus (Flixbus, Amtrak), 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. Train

    best
    1. Take the train from Woodstock to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    8h 57m
    $123–374

  2. Bus

    cheapest
    1. Take the bus from Woodstock to Detroit Bus Stationbus bus FlixBus N2706 / ...
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    11h 45m
    $64–125

  3. Bus, train

    1. Take the bus from Woodstock to Detroit Bus Stationbus bus FlixBus N2706 / ...
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    11h 29m
    $113–234

  4. Drive 428.6 mi

    1. Drive from Woodstock to Chicagocar car 428.6 mi
    7h 8m
    $99–142

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

    1. Take the bus from Woodstock to Toronto Pearson Airportbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 20m
    $344–1,125

  6. Bus via Detroit

    1. Take the bus from Woodstock to Detroit Bus Stationbus bus FlixBus N2706 / ...
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    11h 57m
    $114–180

  7. Train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Woodstock to Toronto Union Stationtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 38m
    $206–1,469

  8. Train to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the train from Woodstock to Toronto Union Stationtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 29m
    $166–599

  9. Drive to Erie International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Woodstock to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    6h 20m
    $95–344

  10. Bus, shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Woodstock to Toronto Pearson Airportbus bus
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 26m
    $264–515

  11. Bus, shuttle to Detroit, fly to Chicago Midway International Airport

    1. Take the bus from Woodstock to Londonbus bus
    2. Take a shuttle bus from Days Inn by Wyndham London to Detroit Airportshuttle bus
    3. Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane plane DTW - MDW
    8h 20m
    $182–568

Woodstock to Chicago by train and car

Calendar21Weekly Services
Duration8h 57mAverage Duration
Ticket$123Cheapest Price
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Questions & Answers

Map of how to get from Woodstock to Chicago.ExpandLaunch map view
  • Distance: 423.3 mi
  • Duration: 8h 57m

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

You can take a train from Woodstock to Chicago Union Station via Windsor and Detroit in around 8h 57m. Alternatively, you can take a bus from Woodstock to Chicago Bus Station via Detroit Bus Station in around 11h 45m.

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