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

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There are 10 ways to get from Orillia to Chicago by bus, plane, train, bus (Flixbus, Greyhound), car, or shuttle

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 Transit to VAUGHAN - HWY 407 terminalbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 45m
    $203–496

  2. Bus

    cheapest
    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus 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 12m
    $86–171

  3. Bus, train via Detroit

    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus bus
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    13h 44m
    $96–221

  4. Drive 547.2 mi

    1. Drive from Orillia to Chicagocar car 547.2 mi
    10h 40m
    $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 407 terminalbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    7h 25m
    $215–507

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

    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus 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
    8h 25m
    $193–646

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

    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus bus
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    7h 15m
    $135–497

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

    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus 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
    8h 14m
    $223–906

  9. Bus via Kitchener

    1. Take the bus from Orillia Transit to VAUGHAN - HWY 407 terminalbus 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 Bus Station to Chicago Bus Stationbus bus
    16h 37m
    $89–180

  10. Bus, train

    1. Take the bus from Orillia Transit to Toronto 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
    $108–319

Orillia to Chicago by bus, subway, train, and car

Calendar21Weekly Services
Duration13h 44mAverage Duration
Ticket$96Cheapest Price
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Questions & Answers

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

You can take a bus from Orillia Transit to Chicago Bus Station via VAUGHAN - HWY 407 terminal, Hwy 407 Bus Terminal, Pearson International Airport Terminal 1, Toronto Pearson Airport, and Detroit Bus Station in around 16h 12m.

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Need to know: Greyhound

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