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How to get fromOshawa to Milwaukeeby train, plane, train (Amtrak), bus (Flixbus), car, or bus

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There are 8 ways to get from Oshawa to Milwaukee by train, plane, train (Amtrak), bus (Flixbus), car, 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 to Toronto Pearson International Airport, fly to General Mitchell International Airport

    best
    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to General Mitchell International Airport (MKE)plane plane YYZ - MKE
    7h 47m
    $81–574

  2. Train via Detroit

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    4. Take the train from Chicago Union Station to Milwaukeetrain train
    14h 59m
    $156–574

  3. Bus

    1. Take the bus from Simcoe St. N. @ Richmond St. E. to Square Onebus bus 56
    2. Take the bus from Mississauga to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Milwaukee Intermodal Stationbus bus
    18h 9m
    $97–154

  4. Drive  631.1 mi

    1. Drive from Oshawa to Milwaukeecar car 631.1 mi
    10h 53m
    $145–209

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

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    3. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    7h 35m
    $212–1,666

  6. Train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport, bus

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    3. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    7h 54m
    $402–1,166

  7. Bus via Kitchener

    1. Take the bus from Simcoe St. S. @ Athol St. E. to Bramalea GO Busbus bus 56
    2. Take the bus from Bramalea GO Bus to Kitchener GO Busbus bus 30 / ...
    3. Take the bus from Kitchener to Detroit Bus Stationbus bus
    4. Take the bus from Detroit Bus Station to Milwaukee Intermodal Stationbus bus
    18h 25m
    $105–155

  8. Train

    1. Take the train from Durham College Oshawa GO to Union Station GOtrain train Le
    2. Take the train from Toronto Union Station to Buffalotrain train
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    4. Take the train from Chicago Union Station to Milwaukeetrain train
    21h 2m
    $191–542

Oshawa to Milwaukee by train and car

Calendar21Weekly Services
Duration14h 59mAverage Duration
Ticket$156Cheapest Price
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Comparing Your Travel Options

Map of how to get from Oshawa to Milwaukee.ExpandLaunch map view
  • Distance: 473.4 mi
  • Duration: 7h 47m

What companies run services between Oshawa, ON, Canada and Milwaukee, WI, USA?

You can take a train from Oshawa to Milwaukee via Toronto Union Station, Windsor, Detroit, and Chicago Union Station in around 14h 59m. Alternatively, you can take a bus from Simcoe St. N. @ Richmond St. E. to Milwaukee Intermodal Station via Square One, Mississauga, and Detroit Bus Station in around 18h 9m.

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