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

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There are 10 ways to get from Chicago to Oakville by plane, train, train (Amtrak), bus (Amtrak, Flixbus), car, bus, or bus (Greyhound, 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 Union Station GO to Oakville GOtrain train
    5h 57m
    $520–1,429

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Detroit Bus Stationbus bus Greyhound US0160
    2. Take the bus from Detroit Bus Station to Mississaugabus bus FlixBus N2706
    14h 20m
    $119–189

  3. Train via Detroit

    1. Take the train from Chicago Union Station to Detroittrain train Wolverine
    2. Take the train from Windsor to Oakvilletrain train VIA Rail
    10h 18m
    $293–625

  4. Bus via Detroit

    1. Take the bus from Chicago Union Station to Detroitbus bus Amtrak Thruway Connecting Service
    2. Take the bus from Detroit Bus Station to Mississaugabus bus FlixBus N2706
    14h 11m

  5. Drive  783.4 km

    1. Drive from Chicago to Oakvillecar car 783.4 km
    8h 12m
    $157–226

  6. 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 Union Station GO to Oakville GOtrain train
    5h 47m
    $291–2,016

  7. 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 Niagara Fallsbus bus
    3. Take the train from Canadian Border to Oakvilletrain train
    8h 37m
    $308–547

  8. 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 Niagara Fallsbus bus
    3. Take the train from Canadian Border to Oakvilletrain train
    8h 20m
    $288–557

  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 Oakvilletrain train
    9h 16m
    $315–1,699

  10. Train

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train Lake Shore Limited
    2. Take the train from Buffalo to Oakvilletrain train VIA Rail
    15h 10m
    $441–853

Chicago to Oakville by train and car

Calendar21Weekly Services
Duration10h 18mAverage Duration
Ticket$293Cheapest Price
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Comparing Your Travel Options

Map of how to get from Chicago to Oakville.ExpandLaunch map view
  • Distance: 789.7 km
  • Duration: 5h 57m

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

You can take a train from Chicago Union Station to Oakville via Detroit and Windsor in around 10h 18m. Alternatively, you can take a bus from Chicago Union Station to Oakville GO Bus via Detroit, Cass & Milwaukee, Larned & Shelby, Detroit Bus Station, Mississauga, and Square One in around 14h 11m.

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