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

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There are 9 ways to get from Orillia 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 Orillia Downtown Terminal Bus Stop to Toronto Pearson Airportbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 12m
    $403–972

  2. Bus

    cheapest
    1. Take the bus from Orillia Downtown Terminal Bus Stop 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
    16h
    $86–142

  3. Bus, train via Detroit

    1. Take the bus from Orillia Downtown Terminal Bus Stop 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
    13h 45m
    $138–409

  4. Drive  570.8 mi

    1. Drive from Orillia to Chicagocar car 570.8 mi
    9h 36m
    $131–189

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

    1. Take the bus from Orillia Transit to Vaughan - Hwy 407bus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    7h 4m
    $191–1,431

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

    1. Take the bus from Orillia Downtown Terminal Bus Stop to Toronto Pearson Airportbus 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 21m
    $189–357

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

    1. Take the bus from Orillia Downtown Terminal Bus Stop to Toronto Pearson Airportbus 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 40m
    $199–347

  8. Bus via Kitchener

    1. Take the bus from Orillia Transit to Vaughan - Hwy 407bus bus
    2. Take the bus from Hwy 407 Bus Terminal 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
    17h 10m
    $110–174

  9. Bus, train

    1. Take the bus from Orillia Downtown Terminal Bus Stop 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
    18h 44m
    $174–501

Orillia to Chicago by bus, train, and car

Calendar4Weekly Services
Duration13h 45mAverage Duration
Ticket$138Cheapest Price
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Comparing Your Travel Options

Map of how to get from Orillia to Chicago.ExpandLaunch map view
  • Distance: 530.8 mi
  • Duration: 6h 12m

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

You can take a bus from Orillia Downtown Terminal Bus Stop to Chicago Bus Station via Toronto Pearson Airport and Detroit Bus Station in around 16h.

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Train operators
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