Rome2Rio

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

Find Transport to Oakville

See all options

There are 10 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 42m
    $261–1,918

  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 31m
    $107–204

  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
    $182–524

  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 55m
    $169–253

  5. Drive  783.4 km

    1. Drive from Chicago to Oakvillecar car 783.4 km
    8h 22m
    $156–226

  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
    6h 2m
    $520–1,531

  7. 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 26m
    $380–611

  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 5m
    $360–621

  9. 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
    $123–512

  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
    $233–664

Chicago to Oakville by train and car

Calendar21Weekly Services
Duration10h 18mAverage Duration
Ticket$182Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Oakville.ExpandLaunch map view
  • Distance: 783.7 km
  • Duration: 5h 42m

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 55m.

Airlines
Train operators
Bus operators

Want to know more about travelling around Canada

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers