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How to get fromChicago to Oshawaby plane, train, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or bus (Amtrak, Flixbus)

Find Transport to Oshawa

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There are 11 ways to get from Chicago to Oshawa by plane, train, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or bus (Amtrak, 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. Fly Chicago O'Hare International Airport to Toronto Pearson International Airport, train

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ)plane plane ORD - YYZ
    2. Take the train from Toronto Union Station to Oshawatrain train
    6h 34m
    $574–1,620

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Detroit Bus Stationbus bus
    2. Take the bus from Detroit Bus Station to Mississaugabus bus
    3. Take the bus from Square One to Centre St. S. @ Athol St. W.bus bus 56
    15h 47m
    $124–198

  3. Train via Detroit

    1. Take the train from Chicago Union Station to Detroittrain train
    2. Take the train from Windsor to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    12h 17m
    $197–755

  4. Drive  868.5 km

    1. Drive from Chicago to Oshawacar car 868.5 km
    9h 3m
    $177–255

  5. Fly Chicago O'Hare International Airport to Toronto Island Airport, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Island Airport (YTZ)plane plane ORD - YTZ
    2. Take the train from Toronto Union Station to Oshawatrain train
    6h 21m
    $295–2,207

  6. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane plane ORD - BUF
    2. Take the bus from Buffalo to Torontobus bus
    3. Take the train from Toronto Union Station to Oshawatrain train
    9h 42m
    $285–737

  7. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane plane MDW - BUF
    2. Take the bus from Buffalo to Torontobus bus
    3. Take the train from Toronto Union Station to Oshawatrain train
    9h 22m
    $275–747

  8. Fly Chicago O'Hare International Airport to Rochester, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Rochester (ROC)plane plane ORD - ROC
    2. Take the train from Rochester to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    11h 40m
    $246–1,409

  9. Fly Chicago Midway International Airport to Rochester, train

    1. Fly from Chicago Midway International Airport (MDW) to Rochester (ROC)plane plane MDW - ROC
    2. Take the train from Rochester to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    11h 21m
    $316–1,809

  10. Bus via Kitchener

    1. Take the bus from Chicago Union Station to Detroitbus bus
    2. Take the bus from Detroit Bus Station to Kitchenerbus bus
    3. Take the bus from Kitchener GO Bus to Bramalea GO Busbus bus 30
    4. Take the bus from Bramalea GO Bus to Centre St. S. @ Athol St. W.bus bus 56
    16h 3m
    $164–232

  11. Train

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train
    2. Take the train from Buffalo to Toronto Union Stationtrain train
    3. Take the train from Union Station GO to Durham College Oshawa GOtrain train Le
    17h 35m
    $245–729

Chicago to Oshawa by train and car

Calendar21Weekly Services
Duration12h 17mAverage Duration
Ticket$197Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Oshawa.ExpandLaunch map view
  • Distance: 806.1 km
  • Duration: 6h 34m

What companies run services between Chicago, IL, USA and Oshawa, ON, Canada?

You can take a train from Chicago Union Station to Oshawa via Detroit, Windsor, and Toronto Union Station in around 12h 17m. Alternatively, you can take a bus from Chicago Bus Station to Centre St. S. @ Athol St. W. via Detroit Bus Station, Mississauga, and Square One in around 15h 47m.

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Want to know more about travelling around Canada

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