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

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There are 10 ways to get from Orillia 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 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 10m
    $344–1,124

  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
    15h 40m
    $87–164

  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 46m
    $169–431

  4. Drive 547.2 mi

    1. Drive from Orillia to Chicagocar car 547.2 mi
    10h 39m
    $126–181

  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 3m
    $181–1,331

  6. Bus, shuttle 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 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 16m
    $264–574

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

    1. Take the bus from Orillia Transit to Vaughan - Hwy 407bus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 54m
    $151–451

  8. Bus, shuttle 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 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 39m
    $254–444

  9. 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 Detroit to Chicago Union Stationbus bus
    17h 10m
    $149–237

  10. Bus, train

    1. Take the bus from Orillia Transit to Union Station Bus Terminalbus 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 54m
    $213–551

Orillia to Chicago by bus, train, and car

Calendar5Weekly Services
Duration13h 46mAverage Duration
Ticket$169Cheapest Price
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Questions & Answers

Map of how to get from Orillia to Chicago.ExpandLaunch map view
  • Distance: 530.8 mi
  • Duration: 6h 10m

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 15h 40m.

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