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How to get fromWindsor to Illinoisby bus (Greyhound, Flixbus), train (Amtrak), car, plane, bus (Amtrak), bus, or train

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There are 8 ways to get from Windsor to Illinois by bus (Greyhound, Flixbus), train (Amtrak), car, plane, bus (Amtrak), bus, or train

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

    best
    1. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    6h 15m
    $41–76

  2. Train (Amtrak)

    1. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    6h 27m
    $78–203

  3. Drive  284.4 mi

    1. Drive from Windsor to Chicagocar car 284.4 mi
    4h 47m
    $66–94

  4. Drive to Detroit, fly to Chicago Midway International Airport

    1. Drive from Windsor to Michigan & Casscar car
    2. Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane plane DTW - MDW
    3h 56m
    $135–468

  5. Bus via Woodward & Baltimore Milwaukee (Amtrak)

    1. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    6h 48m
    $68–98

  6. Fly Detroit to Chicago O'Hare International Airport

    1. Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)plane plane DTW - ORD
    4h 17m
    $135–658

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

    1. Take the bus from Detroit Bus Station to Flintbus bus
    2. Fly from Bishop International Airport (FNT) to Chicago O'Hare International Airport (ORD)plane plane FNT - ORD
    5h 2m
    $42–260

  8. Fly Detroit to South Bend, train

    1. Fly from Detroit (DTW) to South Bend (SBN)plane plane DTW - SBN
    2. Take the train from South Bend Airport to Van Buren St.train train
    5h 49m
    $92–620

Detroit (DTW) to Chicago Midway International Airport (MDW) flights

Calendar41Weekly Planes
Duration1h 12mAverage Duration
Ticket$57Cheapest Price
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Comparing Your Travel Options

Map of how to get from Windsor to Illinois.ExpandLaunch map view
  • Distance: 290.5 mi
  • Duration: 6h 15m

What companies run services between Windsor, ON, Canada and Illinois, USA?

Greyhound USA operates a bus from Detroit Bus Station to Chicago Bus Station 3 times a day. Tickets cost $45–75 and the journey takes 6h 5m. Flixbus USA also services this route twice daily. Alternatively, Amtrak operates a train from Detroit to Chicago Union Station 3 times a day. Tickets cost $75–200 and the journey takes 5h 6m.

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Need to know: Greyhound

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