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

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There are 10 ways to get from Oshawa to Milwaukee by train, plane, train (Amtrak), bus (Flixbus), car, bus, or shuttle

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 40m
    $612–1,446

  2. Bus

    cheapest
    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 12m
    $103–175

  3. 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
    $187–606

  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
    $193–1,472

  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
    $353–1,272

  7. Train to Toronto Island Airport, fly to Chicago Midway International Airport, train

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    3. Take the train from Chicago Union Station to Milwaukeetrain train
    8h 25m
    $181–641

  8. Train, shuttle to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport, bus

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    4. Take the bus from Chicago to Milwaukee Intermodal Stationbus bus
    9h 23m
    $263–662

  9. 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 35m
    $106–180

  10. 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
    20h 57m
    $237–603

Oshawa to Milwaukee by train and car

Calendar21Weekly Services
Duration14h 59mAverage Duration
Ticket$187Cheapest Price
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Questions & Answers

Map of how to get from Oshawa to Milwaukee.ExpandLaunch map view
  • Distance: 473.4 mi
  • Duration: 7h 40m

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 12m.

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