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

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

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 Island Airport, train

    best
    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 39m
    $241–1,818

  2. Train, bus

    cheapest
    1. Take the train from Van Buren St. to Gary Metro Centertrain train Ssl
    2. Take the bus from Gary Bus Station to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Mississaugabus bus
    16h 30m
    $116–209

  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
    $206–548

  4. Bus

    1. Take the bus from Chicago Union Station to Dearbornbus bus Amtrak Thruway Connecting Service
    2. Take the bus from Detroit Bus Station to Mississaugabus bus FlixBus N2706
    13h 54m
    $193–285

  5. Drive 790 km

    1. Drive from Chicago to Oakvillecar car 790 km
    8h 14m
    $157–227

  6. Fly Chicago O'Hare International Airport to Toronto Pearson International Airport, train

    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 58m
    $480–1,531

  7. Fly Chicago Midway International Airport to Toronto Island Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Toronto Island Airport (YTZ)plane plane MDW - YTZ
    2. Take the train from Union Station GO to Oakville GOtrain train
    5h 28m
    $201–618

  8. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane plane MDW - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle bus
    7h 3m
    $360–791

  9. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane plane ORD - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle bus
    7h 28m
    $350–611

  10. Fly Chicago O'Hare International Airport to Erie International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Erie International Airport (ERI)plane plane ORD - ERI
    2. Drive from Erie-Airport-ERI to Oakvillecar car
    6h 40m
    $128–527

  11. 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
    $278–708

Chicago to Oakville by train and car

Calendar21Weekly Services
Duration10h 18mAverage Duration
Ticket$206Cheapest Price
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Questions & Answers

Map of how to get from Chicago to Oakville.ExpandLaunch map view
  • Distance: 783.7 km
  • Duration: 5h 39m

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 Dearborn Transit Center, Cass & Michigan, Rosa Parks Transit Center - Bay 10, Lafayette & Fifth, Detroit Bus Station, Mississauga, and Square One in around 13h 54m.

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