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How to get fromWaukegan to Windsorby train, bus, train (Amtrak), car, subway, plane, or bus (Flixbus)

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There are 9 ways to get from Waukegan to Windsor by train, bus, train (Amtrak), car, subway, plane, or bus (Flixbus)

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, bus

    best
    1. Take the train from Waukegan to Chicago OTCtrain train Up-N
    2. Take the bus from Chicago Union Station to Detroitbus bus Amtrak Thruway Connecting Service
    8h 18m
    $106–158

  2. Train to Chicago O'Hare International Airport, fly to Bishop International Airport, bus

    cheapest
    1. Take the train from Waukegan to Clybourntrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Bishop International Airport (FNT)plane plane ORD - FNT
    3. Take the bus from Flint to Detroit Bus Stationbus bus
    7h 17m
    $75–420

  3. Train

    1. Take the train from Waukegan to Chicago OTCtrain train Up-N
    2. Take the train from Chicago Union Station to Detroittrain train Wolverine
    8h 25m
    $108–255

  4. Drive  522 km

    1. Drive from Waukegan to Windsorcar car 522 km
    5h 36m
    $106–153

  5. Train, subway to Chicago Midway International Airport, fly to Detroit

    1. Take the train from Waukegan to Chicago OTCtrain train
    2. Take the subway from Clark/Lake to Midwaysubway subway
    3. Fly from Chicago Midway International Airport (MDW) to Detroit (DTW)plane plane MDW - DTW
    5h 55m
    $205–672

  6. Bus

    1. Take the bus from Tornado Bus Co - Waukegan to Water & Chicago - Circle Kbus bus Milwaukee
    2. Take the bus from Milwaukee Intermodal Station to Detroit Bus Stationbus bus FlixBus 2550
    9h 45m
    $91–166

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

    1. Take the train from Waukegan to Clybourntrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Detroit (DTW)plane plane ORD - DTW
    6h 9m
    $206–973

  8. Bus to General Mitchell International Airport, fly to Detroit

    1. Take the bus from Metro Train Station - 13th Avenue and 54th Street to Mitchell Airportbus bus
    2. Fly from General Mitchell International Airport (MKE) to Detroit (DTW)plane plane MKE - DTW
    6h 14m
    $1,019–1,532

  9. Train, train to South Bend, fly to Detroit

    1. Take the train from Waukegan to Chicago OTCtrain train
    2. Take the train from Millennium Station to South Bend Airporttrain train
    3. Fly from South Bend (SBN) to Detroit (DTW)plane plane SBN - DTW
    7h 59m
    $111–641

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

Calendar40Weekly Planes
Duration1h 10mAverage Duration
Ticket$103Cheapest Price
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Comparing Your Travel Options

Map of how to get from Waukegan to Windsor.ExpandLaunch map view
  • Distance: 528.4 km
  • Duration: 8h 18m

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

You can take a train from Waukegan to Windsor via Chicago OTC, Madison & Canal, Clinton & Jackson, Chicago Union Station, Detroit, Baltimore St - Southbound, and Congress St in around 8h 25m. Alternatively, you can take a bus from Tornado Bus Co - Waukegan to Windsor via Water & Chicago - Circle K, Milwaukee Intermodal Station, and Detroit Bus Station in around 9h 45m.

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