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

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There are 8 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 bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    8h 5m
    $351–1,035

  2. Bus

    cheapest
    1. Take the bus from Owen Sound to Toronto Pearson Airportbus bus
    2. Take the bus from Toronto Pearson Airport to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    17h 35m
    $89–175

  3. Bus, train

    1. Take the bus from Owen Sound to Guelphbus bus
    2. Take the train from Guelph to Sarniatrain train
    3. Take the train from Port Huron Station to Chicago Union Stationtrain train
    14h 36m

  4. Drive 489.3 mi

    1. Drive from Owen Sound to Chicagocar car 489.3 mi
    9h 22m
    $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 bus
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    9h 11m
    $271–525

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

    1. Take the bus from Owen Sound to Guelphbus bus
    2. Take the train from Guelph Central GO to Union Station GOtrain train
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    9h 40m

  7. Bus, train to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the bus from Owen Sound to Guelphbus bus
    2. Take the train from Guelph Central GO to Union Station GOtrain train
    3. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    9h 31m

  8. Bus, shuttle

    1. Take the bus from Owen Sound to Guelphbus bus
    2. Take the bus from Guelph to Londonbus bus
    3. Take a shuttle bus from Days Inn by Wyndham London to Detroit Airportshuttle bus
    4. Take the bus from Dearborn to Chicago Union Stationbus bus
    17h 49m

Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) flights

Calendar123Weekly Planes
Duration2h 2mAverage Duration
Ticket$41Cheapest Price
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Questions & Answers

Map of how to get from Owen Sound to Chicago.ExpandLaunch map view
  • Distance: 581.5 mi
  • Duration: 8h 5m

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 35m.

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