Rome2Rio

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

Find Transport to Chicago Loop

See all options

There are 10 ways to get from Oakville to Chicago Loop by train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, subway, or shuttle

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 Toronto Union Stationtrain
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    5h 58m
    $178–531

  2. Bus

    cheapest
    1. Take the bus from Mississauga to Detroit Bus StationbusFlixBus N2706
    2. Take the bus from Detroit Bus Station to Chicago Bus StationbusGreyhound US0160
    15h 12m
    $78–184

  3. Train via Detroit

    1. Take the train from Oakville to WindsortrainVIA Rail
    2. Take the train from Detroit to Chicago Union StationtrainWolverine
    10h 13m
    $80–227

  4. Drive 491.6 mi

    1. Drive from Oakville to Chicago Loopcar491.6 mi
    8h 8m
    $113–163

  5. Train to Toronto Island Airport, fly to Chicago Midway International Airport, subway

    1. Take the train from Oakville GO to Exhibition GOtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    3. Take the subway from Midway to Washington/Wellssubway
    5h 28m
    $131–455

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

    1. Take the train from Oakville GO to Exhibition GOtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    5h 31m
    $191–485

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

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)planeYYZ - MDW
    7h 35m
    $348–931

  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
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    7h 20m
    $198–801

  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
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    7h 32m
    $173–651

  10. Train

    1. Take the train from Oakville to BuffalotrainVIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union StationtrainLake Shore Limited
    15h 14m
    $86–293

Oakville to Chicago Loop by train and car

Calendar21Weekly Services
Duration10h 13mAverage Duration
Ticket$80Cheapest Price
See schedules

Questions & Answers

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 12m.

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

More Questions & Answers

Trips from Oakville

Trips to Chicago Loop

Popular routes