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How to get fromOakville to Chicagoby train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, 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, shuttle, 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 Island 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 Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 42m
    $178–1,313

  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
    14h 58m
    $80–151

  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
    $145–394

  4. Drive 490.8 mi

    1. Drive from Oakville to Chicagocar car 490.8 mi
    8h 12m
    $113–163

  5. Train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    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 1m
    $338–1,113

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

    1. Take the train from Oakville GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    5h 33m
    $148–433

  7. 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 41m
    $82–322

  8. 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 7m
    $258–563

  9. 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 30m
    $248–433

  10. Bus via Detroit

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    15h 10m
    $140–216

  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
    $196–515

Oakville to Chicago by train and car

Calendar21Weekly Services
Duration10h 13mAverage Duration
Ticket$145Cheapest Price
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Questions & Answers

Map of how to get from Oakville to Chicago.ExpandLaunch map view
  • Distance: 487 mi
  • Duration: 5h 42m

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 14h 58m.

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