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

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

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 Naperville to Chicago Union Stationtrain train Bnsf
    2. Take the train from Chicago Union Station to Detroittrain train Wolverine
    7h 56m
    $72–198

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Detroit Bus Stationbus bus Greyhound US0160
    9h 58m
    $53–120

  3. Drive 493.9 km

    1. Drive from Naperville to Windsorcar car 493.9 km
    5h 21m
    $98–141

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

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Take the subway from LaSalle/Van Buren to Midwaysubway subway
    3. Fly from Chicago Midway International Airport (MDW) to Detroit (DTW)plane plane MDW - DTW
    5h 30m
    $83–568

  5. Train, bus

    1. Take the train from Naperville to Chicago Union Stationtrain train Bnsf
    2. Take the bus from Chicago to Detroit Bus Stationbus bus FlixBus 2552
    10h 15m
    $70–155

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

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Fly from Chicago O'Hare International Airport (ORD) to Detroit (DTW)plane plane ORD - DTW
    5h 46m
    $173–488

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

    1. Take the train from Naperville to Chicago Union Stationtrain 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 2m
    $80–420

  8. Train, train to General Mitchell International Airport, fly to Detroit

    1. Take the train from Naperville to Chicago Union Stationtrain train
    2. Take the train from Chicago Union Station to Milwaukeetrain train
    3. Fly from General Mitchell International Airport (MKE) to Detroit (DTW)plane plane MKE - DTW
    7h 37m
    $473–926

Naperville to Windsor by train and tram

Calendar21Weekly Services
Duration7h 56mAverage Duration
Ticket$72Cheapest Price
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Questions & Answers

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

You can take a train from Naperville to Congress St via Chicago Union Station, Detroit, and Baltimore St - Southbound in around 7h 56m. Alternatively, Greyhound USA operates a bus from Chicago Bus Station to Detroit Bus Station 3 times a day. Tickets cost $45–95 and the journey takes 6h 5m. Flixbus USA also services this route twice daily.

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