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

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There are 11 ways to get from Oakville to Chicago by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus, 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 Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the train from Oakville GO to Union Station GOtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 4m
    $398–1,013

  2. Fly Toronto Pearson International Airport to Chicago Midway International Airport

    cheapest
    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    7h 23m
    $53–313

  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
    $205–441

  4. Bus

    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 6m
    $80–135

  5. Drive  487.6 mi

    1. Drive from Oakville to Chicagocar car 487.6 mi
    8h 12m
    $112–162

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

    1. Take the train from Oakville GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 55m
    $208–1,413

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

    1. Take the train from Oakville to Canadian Bordertrain train
    2. Take the bus from Niagara Falls to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 55m
    $210–402

  8. Train to Rochester, fly to Chicago Midway International Airport

    1. Take the train from Oakville to Rochestertrain train
    2. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    8h 18m
    $147–712

  9. Train, bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Oakville to Canadian Bordertrain train
    2. Take the bus from Niagara Falls to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    8h 20m
    $220–392

  10. 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
    $315–612

  11. Bus via Dearborn

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Dearborn to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    15h 24m

Oakville to Chicago by bus and foot

Calendar5Weekly Services
Duration15h 6mAverage Duration
Ticket$80Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Oakville to Chicago.ExpandLaunch map view
  • Distance: 490.7 mi
  • Duration: 6h 4m

What companies run services between Oakville, ON, Canada and Chicago, 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 Chicago Bus Station via Square One, Mississauga, and Detroit Bus Station in around 15h 6m.

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Want to know more about travelling around United States

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