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

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There are 11 ways to get from Oshawa to Chicago by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, or bus (Flixbus, Amtrak)

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 Island Airport, fly to Chicago O'Hare International Airport

    best
    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
    5h 50m
    $181–1,448

  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 Chicago Bus Stationbus bus
    16h 37m
    $88–160

  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
    12h 30m
    $160–546

  4. Drive 543.3 mi

    1. Drive from Oshawa to Chicagocar car 543.3 mi
    9h 11m
    $125–180

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

    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
    6h 9m
    $341–1,248

  6. Train to Toronto Island Airport, fly to Chicago Midway International Airport

    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
    5h 41m
    $151–568

  7. Train, shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    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 Midway International Airport (MDW)plane plane BUF - MDW
    7h 15m
    $261–698

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

    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
    7h 38m
    $251–568

  9. Train, train to Rochester, fly to Chicago Midway International Airport

    1. Take the train from Oshawa to Toronto Union Stationtrain train
    2. Take the train from Toronto Union Station to Rochestertrain train
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    10h 25m
    $150–792

  10. 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 to Chicago Union Stationbus bus
    17h 12m
    $151–225

  11. 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
    18h 28m
    $210–543

Oshawa to Chicago by train and car

Calendar21Weekly Services
Duration12h 30mAverage Duration
Ticket$160Cheapest Price
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Questions & Answers

Map of how to get from Oshawa to Chicago.ExpandLaunch map view
  • Distance: 497.2 mi
  • Duration: 5h 50m

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

You can take a train from Oshawa to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 12h 30m. Alternatively, you can take a bus from Simcoe St. N. @ Richmond St. E. to Chicago Bus Station via Square One, Mississauga, and Detroit Bus Station in around 16h 37m.

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