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

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There are 11 ways to get from Oakville to Chicago Loop by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, subway, 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 Oakville GO to Toronto Union Stationtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 58m
    $188–530

  2. Bus

    cheapest
    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    15h 12m
    $73–189

  3. Train via Detroit

    1. Take the train from Oakville to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    10h 13m
    $75–226

  4. Drive 491.6 mi

    1. Drive from Oakville to Chicago Loopcar car 491.6 mi
    8h 12m
    $113–163

  5. Drive to Erie International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Oakville to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    5h 39m
    $82–322

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

    1. Take the train from Oakville GO to Exhibition GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 40m
    $191–496

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

    1. Take the train from Oakville GO to Exhibition GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    3. Take the subway from Midway to Washington/Wellssubway subway
    5h 36m
    $111–466

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

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 38m
    $173–660

  9. Shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 35m
    $198–900

  10. Train to Detroit, fly to Chicago Midway International Airport

    1. Take the train from Oakville to Windsortrain train
    2. Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane plane DTW - MDW
    8h 18m
    $84–422

  11. Train

    1. Take the train from Oakville to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    15h 14m
    $86–292

Oakville to Chicago Loop by train and car

Calendar21Weekly Services
Duration10h 13mAverage Duration
Ticket$75Cheapest Price
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Questions & Answers

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

You can take a train from Oakville to Chicago Union Station via Windsor and Detroit in around 10h 13m. Alternatively, you can take a bus from Oakville GO Bus to Washington & Lasalle via Square One, Mississauga, Detroit Bus Station, Chicago Bus Station, and Jefferson & Harrison in around 15h 12m.

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