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How to get fromOrangeville to Chicagoby bus, plane, train, bus (Flixbus, Greyhound), car, or bus (Flixbus, Amtrak)

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There are 10 ways to get from Orangeville to Chicago by bus, plane, train, bus (Flixbus, Greyhound), car, 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 Townline @ Mill St. to Bramalea GO Busbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 10m
    $402–966

  2. Bus to Toronto Pearson International Airport, fly to Chicago Midway International Airport

    cheapest
    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    7h 45m
    $57–316

  3. Bus, train via Detroit

    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus 37
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    13h 22m
    $138–389

  4. Bus

    1. Take the bus from Broadway @ John St. to Bramalea GO Busbus bus 37
    2. Take the bus from Bramalea GO Bus to Kitchener GO Busbus bus 30 / ...
    3. Take the bus from Kitchener to Detroit Bus Stationbus bus
    4. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    16h 5m
    $85–135

  5. Drive  485.9 mi

    1. Drive from Orangeville to Chicagocar car 485.9 mi
    8h 49m
    $112–161

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

    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 44m
    $194–1,421

  7. Bus, bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus
    2. Take the bus from Toronto Pearson Airport to Buffalo Niagara International Airportbus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    9h 20m
    $188–351

  8. Bus, bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus
    2. Take the bus from Toronto Pearson Airport to Buffalo Niagara International Airportbus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    9h 38m
    $198–341

  9. Bus via Dearborn

    1. Take the bus from Broadway @ John St. to Bramalea GO Busbus bus 37
    2. Take the bus from Bramalea GO Bus to Kitchener GO Busbus bus 30 / ...
    3. Take the bus from Kitchener to Detroit Bus Stationbus bus
    4. Take the bus from Dearborn to Chicago Union Stationbus bus
    16h 24m
    $112–177

  10. Bus, train

    1. Take the bus from Broadway @ John St. to Bramalea GO Busbus bus 37
    2. Take the train from Toronto Union Station to Buffalotrain train
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    18h 40m
    $172–486

Orangeville to Chicago by bus, train, and car

Calendar10Weekly Services
Duration13h 22mAverage Duration
Ticket$138Cheapest Price
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Comparing Your Travel Options

Map of how to get from Orangeville to Chicago.ExpandLaunch map view
  • Distance: 490.6 mi
  • Duration: 6h 10m

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

You can take a bus from Broadway @ John St. to Chicago Bus Station via Bramalea GO Bus, Kitchener GO Bus, Kitchener, and Detroit Bus Station in around 16h 5m.

Airlines
Train operators
Bus operators

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