Rome2Rio

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

Find Transport to Oshawa

See all options

There are 11 ways to get from Chicago to Oshawa 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 Toronto Union Station to Oshawatrain train
    6h 16m
    $275–2,207

  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 Kitchenerbus bus
    4. Take the bus from Kitchener GO Bus to Bramalea GO Busbus bus 30 / ...
    5. Take the bus from Bramalea GO Bus to Centre St. S. @ Athol St. W.bus bus 56
    18h 33m
    $140–237

  3. Train via Detroit

    1. Take the train from Chicago Union Station to Detroittrain train
    2. Take the train from Windsor to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    12h 17m
    $198–735

  4. Bus

    1. Take the bus from Chicago Union Station to Dearbornbus bus
    2. Take the bus from Detroit Bus Station to Brampton Bramalea GObus bus
    3. Take the bus from Bramalea GO Bus to Centre St. S. @ Athol St. W.bus bus 56
    15h 7m
    $185–275

  5. Drive  868.4 km

    1. Drive from Chicago to Oshawacar car 868.4 km
    9h 22m
    $174–251

  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 Toronto Union Station to Oshawatrain train
    6h 37m
    $524–1,720

  7. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, shuttle, train

    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
    3. Take the train from Toronto Union Station to Oshawatrain train
    8h 1m
    $384–800

  8. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, shuttle, train

    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
    3. Take the train from Toronto Union Station to Oshawatrain train
    7h 39m
    $364–820

  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 Oshawacar car
    7h 45m
    $144–537

  10. Fly Chicago Midway International Airport to Rochester, train

    1. Fly from Chicago Midway International Airport (MDW) to Rochester (ROC)plane plane MDW - ROC
    2. Take the train from Rochester to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    11h 16m
    $306–1,709

  11. Train

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train
    2. Take the train from Buffalo to Toronto Union Stationtrain train
    3. Take the train from Union Station GO to Durham College Oshawa GOtrain train Le
    17h 35m
    $252–693

Chicago to Oshawa by train and car

Calendar21Weekly Services
Duration12h 17mAverage Duration
Ticket$198Cheapest Price
See schedules

Questions & Answers

Map of how to get from Chicago to Oshawa.ExpandLaunch map view
  • Distance: 800.1 km
  • Duration: 6h 16m

What companies run services between Chicago, IL, USA and Oshawa, ON, Canada?

You can take a train from Chicago Union Station to Oshawa via Detroit, Windsor, and Toronto Union Station in around 12h 17m. Alternatively, you can take a bus from Chicago Union Station to Centre St. S. @ Athol St. W. via Dearborn Transit Center, Cass & Michigan, Rosa Parks Transit Center - Bay 10, Lafayette & Fifth, Detroit Bus Station, Brampton Bramalea GO, and Bramalea GO Bus in around 15h 7m.

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