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

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

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 Orangeville, ON to Toronto Pearson International Airportbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 41m
    $348–1,125

  2. Bus

    cheapest
    1. Take the bus from Orangeville, ON to Toronto Pearson International 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
    15h 4m
    $96–165

  3. Train

    1. Take the train from Brampton to Sarniatrain train VIA Rail
    2. Take the train from Port Huron Station to Chicago Union Stationtrain train Blue Water
    13h 40m
    $147–410

  4. Drive 485.9 mi

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

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

    1. Take the bus from Orangeville, ON to Toronto Pearson International 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
    6h 48m
    $208–575

  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 42m
    $185–1,321

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

    1. Take the bus from Orangeville, ON to Toronto Pearson International Airportbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    7h 2m
    $498–975

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

    1. Take the bus from Orangeville, ON to Toronto Pearson International 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 O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 10m
    $258–515

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

    1. Take the bus from Townline @ Mill St. to Bramalea GO Busbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 33m
    $155–451

  10. Bus via Kitchener

    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 to Chicago Union Stationbus bus
    16h 19m
    $142–215

  11. 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
    $213–546

Orangeville to Chicago by bus, train, and car

Calendar7Weekly Services
Duration13h 40mAverage Duration
Ticket$147Cheapest Price
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Questions & Answers

Map of how to get from Orangeville to Chicago.ExpandLaunch map view
  • Distance: 486.6 mi
  • Duration: 5h 41m

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

You can take a bus from Townline @ Mill St. to Chicago Union Station via Main St. N. @ Nelson St. E., Brampton, Sarnia, and Port Huron Station in around 13h 40m. Alternatively, you can take a bus from Orangeville, ON to Chicago Bus Station via Toronto Pearson International Airport, Toronto airport terminal 3, Toronto Airport-Terminal 1, Toronto Pearson Airport, and Detroit Bus Station in around 15h 4m.

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