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

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There are 9 ways to get from Pickering to Chicago by bus, plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. Line 56 bus to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Brock Rd. @ Hwy. 407 Park & Ride to Richmond Hill Centrebus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    6h 15m
    $173–449

  2. Bus

    cheapest
    1. Take the bus from Brock Rd. @ Hwy. 407 Park & Ride to Square Onebus56
    2. Take the bus from Mississauga to Detroit Bus Stationbus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    15h 57m
    $80–207

  3. Train via Detroit

    1. Take the train from Toronto Union Station to WindsortrainVIA Rail
    2. Take the train from Detroit to Chicago Union StationtrainWolverine
    12h 58m
    $89–243

  4. Drive 532.1 mi

    1. Drive from Pickering to Chicagocar532.1 mi
    8h 54m
    $122–176

  5. Line 112 bus, train to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the bus from Peter Matthews Northbound @ Alexander Knox to Pickering Parkway Terminal Platform B12bus
    2. Take the train from Pickering GO to Toronto Union Stationtrain
    3. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    6h 24m
    $133–438

  6. Line 112 bus, train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Peter Matthews Northbound @ Alexander Knox to Pickering Parkway Terminal Platform B12bus
    2. Take the train from Pickering GO to Toronto Union Stationtrain
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    6h 35m
    $193–488

  7. Shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    7h 29m
    $203–729

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

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    7h 49m
    $178–559

  9. Train

    1. Take the train from Toronto Union Station to BuffalotrainVIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union StationtrainLake Shore Limited
    18h 6m
    $96–295

Pickering to Chicago by bus, train, and car

Calendar21Weekly Services
Duration12h 58mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

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

You can take a bus from Zents Westbound @ Tillings to Chicago Union Station via Pickering Parkway Terminal Platform B12, Pickering GO, Toronto Union Station, Windsor, and Detroit in around 12h 58m. Alternatively, you can take a bus from Brock Rd. @ Hwy. 407 Park & Ride to Chicago Bus Station via Square One, Mississauga, and Detroit Bus Station in around 15h 57m.

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