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

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There are 9 ways to get from Oshawa to Chicago Loop by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, 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 Chicago O'Hare International Airport

    best
    1. Take the train from Durham College Oshawa GO to Toronto Union Stationtrain
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    6h 13m
    $169–530

  2. Bus

    cheapest
    1. Take the bus from Simcoe St. N. @ Richmond St. E. to Square Onebus56
    2. Take the bus from Mississauga to Detroit Bus Stationbus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    16h 51m
    $85–158

  3. Train via Detroit

    1. Take the train from Durham College Oshawa GO to Toronto Union StationtrainLe
    2. Take the train from Toronto Union Station to Windsortrain
    3. Take the train from Detroit to Chicago Union Stationtrain
    12h 41m
    $88–303

  4. Drive 544.1 mi

    1. Drive from Oshawa to Chicago Loopcar544.1 mi
    9h 8m
    $125–180

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

    1. Take the train from Durham College Oshawa GO to Toronto Union Stationtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    6h 15m
    $122–534

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

    1. Take the train from Durham College Oshawa GO to Toronto Union Stationtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    6h 19m
    $192–554

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

    1. Take the train from Durham College Oshawa GO to Toronto Union Stationtrain
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    7h 37m
    $194–790

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

    1. Take the train from Durham College Oshawa GO to Toronto Union Stationtrain
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    7h 50m
    $169–600

  9. Train

    1. Take the train from Durham College Oshawa GO to Toronto Union StationtrainLe
    2. Take the train from Toronto Union Station to Buffalotrain
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain
    18h 19m
    $112–342

Oshawa to Chicago Loop by train and car

Calendar21Weekly Services
Duration12h 41mAverage Duration
Ticket$88Cheapest Price
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Questions & Answers

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

You can take a train from Durham College Oshawa GO to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 12h 41m. Alternatively, you can take a bus from Simcoe St. N. @ Richmond St. E. to Washington & Lasalle via Square One, Mississauga, Detroit Bus Station, Chicago Bus Station, and Jefferson & Harrison in around 16h 51m.

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