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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 10 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 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 9m
    $382–1,116

  2. Bus

    cheapest
    1. Take the bus from Broadway @ John St. to Bramalea GO Busbus bus 37
    2. Take the bus from Brampton Bramalea GO to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    15h 27m
    $77–143

  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
    $132–390

  4. Drive 485.9 mi

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

  5. 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
    $185–1,421

  6. Bus, shuttle 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 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
    7h 15m
    $262–446

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

    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 30m
    $492–966

  8. Bus, shuttle 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 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 43m
    $272–436

  9. 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 Dearborn to Chicago Union Stationbus bus
    16h 24m
    $126–187

  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
    $183–516

Orangeville to Chicago by bus, train, and car

Calendar7Weekly Services
Duration13h 40mAverage Duration
Ticket$132Cheapest Price
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Questions & Answers

Map of how to get from Orangeville to Chicago.ExpandLaunch map view
  • Distance: 490.6 mi
  • Duration: 6h 9m

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 Broadway @ John St. to Chicago Bus Station via Bramalea GO Bus, Brampton Bramalea GO, and Detroit Bus Station in around 15h 27m.

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