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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 bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 15m
    $183–469

  2. Bus

    cheapest
    1. Take the bus from Brock Rd. @ Hwy. 407 Park & Ride to Square Onebus bus 56
    2. Take the bus from Mississauga to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    15h 57m
    $75–192

  3. Train via Detroit

    1. Take the train from Toronto Union Station to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    12h 58m
    $89–238

  4. Drive 532.1 mi

    1. Drive from Pickering to Chicagocar car 532.1 mi
    8h 58m
    $122–176

  5. 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 bus
    2. Take the train from Pickering GO to Toronto Union Stationtrain train
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 35m
    $193–488

  6. 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 bus
    2. Take the train from Pickering GO to Toronto Union Stationtrain train
    3. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 24m
    $123–448

  7. 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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 55m
    $178–599

  8. 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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 44m
    $213–839

  9. Train

    1. Take the train from Toronto Union Station to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 6m
    $106–295

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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