Rome2Rio

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

Find Transport to Chicago Loop

See all options
QR code to download the Rome2Rio app

Download the Rome2Rio travel app

Scan QR code with your phone to download the app

Download on the App StoreGet it on Google Play

There are 11 ways to get from Oakville to Chicago Loop by train (Amtrak), bus (Flixbus, Greyhound), car, train, plane, bus (Flixbus, Amtrak), 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. Train via Detroit

    best
    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
    $205–440

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

    cheapest
    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 8m
    $47–261

  3. 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 18m
    $87–143

  4. Drive  488.5 mi

    1. Drive from Oakville to Chicago Loopcar car 488.5 mi
    8h 13m
    $94–135

  5. 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

  6. 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 26m
    $315–612

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

    1. Take the train from Oakville GO to Exhibition GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 49m
    $208–1,325

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

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    8h 6m
    $62–361

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

    1. Take the train from Oakville GO to Niagara Falls GOtrain train
    2. Take the bus from Niagara Falls USA to Buffalo Niagara International Airportbus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    8h 32m
    $201–480

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

    1. Take the train from Oakville GO to Niagara Falls GOtrain train
    2. Take the bus from Niagara Falls USA to Buffalo Niagara International Airportbus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    8h 45m
    $191–470

  11. Train, train to Rochester, fly to Chicago Midway International Airport

    1. Take the train from Oakville to Canadian Bordertrain train
    2. Take the train from Niagara Falls Amtrak Station to Rochestertrain train
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    8h 12m
    $175–850

Oakville to Chicago Loop by train and car

Calendar21Weekly Services
Duration10h 13mAverage Duration
Ticket$205Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Oakville to Chicago Loop.ExpandLaunch map view
  • Distance: 488.3 mi
  • Duration: 10h 13m

What companies run services between Oakville, ON, Canada and Chicago Loop, 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 Washington & Lasalle via Square One, Mississauga, Detroit Bus Station, Chicago Bus Station, and Jefferson & Harrison in around 15h 18m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

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

Booking & Getting There