Rome2Rio

How to get fromOwen Sound to Chicagoby bus, plane, train, bus (Flixbus, Greyhound), car or shuttle

Find Transport to Chicago

See all options

There are 9 ways to get from Owen Sound to Chicago by bus, plane, train, bus (Flixbus, Greyhound), car, 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. Bus to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    8h 7m
    $179–839

  2. Bus

    cheapest
    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Take the bus from Toronto Pearson Airport to Detroit Bus Stationbus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    17h 55m
    $82–229

  3. Bus, train

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Take the train from Toronto Union Station to Windsortrain
    3. Take the train from Detroit to Chicago Union Stationtrain
    15h 37m
    $99–321

  4. Drive 489.3 mi

    1. Drive from Owen Sound to Chicagocar489.3 mi
    9h 17m
    $112–162

  5. Bus, shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    9h 20m
    $209–799

  6. Bus to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    9h 7m
    $138–612

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

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    9h 18m
    $218–542

  8. Bus, train via London

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus
    2. Take the bus from Pearson International Airport Terminal 1 to London, ON - VIA Railbus
    3. Take the train from London to Sarniatrain
    4. Take the train from Port Huron Amtrak Station to Chicago Union Stationtrain
    16h 3m
    $84–337

  9. Bus, train #2

    1. Take the bus from Owen Sound to Torontobus
    2. Take the train from Toronto Union Station to Buffalotrain
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain
    20h 54m
    $123–306

Owen Sound to Chicago by bus, train, and car

Calendar5Weekly Services
Duration15h 37mAverage Duration
Ticket$99Cheapest Price
See schedules

Questions & Answers

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

You can take a bus from Owen Sound to Chicago Bus Station via Toronto Pearson Airport and Detroit Bus Station in around 17h 55m.

Transport is disrupted due to the Russia-Ukraine war. Read more

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

Where to next?

Trips from Owen Sound

Trips to Chicago

Popular routes