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

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There are 9 ways to get from Owen Sound to Chicago by bus, plane, train, bus (Flixbus, Greyhound), car, shuttle, or bus (Flixbus, Amtrak)

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
    $352–1,137

  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
    $95–177

  3. Bus, train via Detroit

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus bus
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    15h 41m
    $177–444

  4. Drive 489.3 mi

    1. Drive from Owen Sound to Chicagocar car 489.3 mi
    9h 22m
    $112–162

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

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    9h
    $198–1,346

  6. 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
    $272–587

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

    1. Take the bus from Owen Sound to Toronto Pearson Airportbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    8h 51m
    $168–466

  8. Bus via Detroit

    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 to Chicago Union Stationbus bus
    17h 47m
    $155–242

  9. Bus, train

    1. Take the bus from Owen Sound to Torontobus bus
    2. Take the train from Toronto Union Station to Buffalotrain train
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    20h 54m
    $222–566

Owen Sound to Chicago by bus, train, and car

Calendar8Weekly Services
Duration15h 41mAverage Duration
Ticket$177Cheapest 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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