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How to get fromNaperville to Windsorby train (Amtrak), bus (Greyhound, Flixbus), car, train, 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, 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 StationtrainBnsf
    2. Take the train from Chicago Union Station to DearborntrainWolverine
    7h 39m
    $67–171

  2. Train, bus

    cheapest
    1. Take the train from Naperville to Chicago Union StationtrainBnsf
    2. Take the bus from Chicago to Detroit Bus StationbusFlixBus 2552
    10h 13m
    $62–145

  3. Bus

    1. Take the bus from Naperville Amtrak to ChicagobusWaterloo
    2. Take the bus from Chicago Bus Station to Detroit Bus StationbusGreyhound US0160
    7h 50m
    $77–169

  4. Drive 493.9 km

    1. Drive from Naperville to Windsorcar493.9 km
    5h 17m
    $99–143

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

    1. Take the train from Naperville to Chicago Union Stationtrain
    2. Fly from Chicago O'Hare International Airport (ORD) to Detroit (DTW)planeORD - DTW
    5h 42m
    $170–508

  6. Train to Chicago Midway International Airport, fly to Detroit

    1. Take the train from Naperville to Chicago Union Stationtrain
    2. Fly from Chicago Midway International Airport (MDW) to Detroit (DTW)planeMDW - DTW
    5h 33m
    $80–508

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

    1. Take the train from Naperville to Chicago Union Stationtrain
    2. Fly from Chicago O'Hare International Airport (ORD) to Bishop International Airport (FNT)planeORD - FNT
    3. Take the bus from Flint to Detroit Bus Stationbus
    6h 34m
    $109–485

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

    1. Take the train from Naperville to Chicago Union Stationtrain
    2. Take the train from Chicago Union Station to Milwaukeetrain
    3. Fly from General Mitchell International Airport (MKE) to Detroit (DTW)planeMKE - DTW
    7h 39m
    $280–986

Naperville to Windsor by train and bus

Calendar21Weekly Services
Duration7h 39mAverage Duration
Ticket$67Cheapest 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 Cass + Michigan via Chicago Union Station, Dearborn, and Dearborn Transit Center in around 7h 39m. Alternatively, you can take a bus from Naperville Amtrak to Detroit Bus Station via Chicago Bus Station in around 7h 50m.

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