Rome2Rio

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

Find Transport to Oshawa

See all options

There are 11 ways to get from Chicago to Oshawa by plane, train, train (Amtrak), bus (Greyhound, Flixbus), car, bus, or bus (Amtrak, Flixbus)

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 Pearson International Airport, train

    best
    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 29m
    $524–1,620

  2. Bus

    cheapest
    1. Take the bus from Chicago Bus Station to Detroit Bus Stationbus bus
    2. Take the bus from Detroit Bus Station to Mississaugabus bus
    3. Take the bus from Square One to Centre St. S. @ Athol St. W.bus bus 56
    15h 53m
    $128–206

  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 14m
    $309–835

  4. Drive  868.5 km

    1. Drive from Chicago to Oshawacar car 868.5 km
    9h 3m
    $173–250

  5. Fly Chicago O'Hare International Airport to Toronto Island Airport, train

    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 18m
    $295–2,107

  6. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, bus, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane plane ORD - BUF
    2. Take the bus from Buffalo to Torontobus bus
    3. Take the train from Toronto Union Station to Oshawatrain train
    9h 18m
    $285–727

  7. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, bus, train

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane plane MDW - BUF
    2. Take the bus from Buffalo to Torontobus bus
    3. Take the train from Toronto Union Station to Oshawatrain train
    8h 59m
    $295–737

  8. Fly Chicago O'Hare International Airport to Rochester, train

    1. Fly from Chicago O'Hare International Airport (ORD) to Rochester (ROC)plane plane ORD - ROC
    2. Take the train from Rochester to Toronto Union Stationtrain train
    3. Take the train from Toronto Union Station to Oshawatrain train
    11h 30m
    $246–1,359

  9. 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 13m
    $346–1,909

  10. Bus via Kitchener

    1. Take the bus from Chicago Union Station to Detroitbus bus
    2. Take the bus from Detroit Bus Station to Kitchenerbus bus
    3. Take the bus from Kitchener GO Bus to Bramalea GO Busbus bus 30 / ...
    4. Take the bus from Bramalea GO Bus to Centre St. S. @ Athol St. W.bus bus 56
    16h 9m

  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
    $454–874

Chicago to Oshawa by bus and foot

Calendar5Weekly Services
Duration15h 53mAverage Duration
Ticket$128Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Chicago to Oshawa.ExpandLaunch map view
  • Distance: 806.1 km
  • Duration: 6h 29m

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 14m. Alternatively, you can take a bus from Chicago Bus Station to Centre St. S. @ Athol St. W. via Detroit Bus Station, Mississauga, and Square One in around 15h 53m.

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

Booking & Getting There