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

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There are 8 ways to get from Pickering to Chicago by bus, plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. 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 12m
    $401–1,017

  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 56m
    $83–140

  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
    13h
    $216–460

  4. Drive  528.9 mi

    1. Drive from Pickering to Chicagocar car 528.9 mi
    8h 53m
    $121–175

  5. Line 118 bus, train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Sideline 24 Southbound @ Flagship to Pickering Parkway Terminal Platform B12bus bus
    2. Take the train from Pickering GO to Union Station GOtrain train
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 36m

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

    1. Take the bus from Toronto to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    10h 23m
    $188–438

  7. Bus via Kitchener

    1. Take the bus from Brock Rd. @ Hwy. 407 Park & Ride to Bramalea GO Busbus bus 56
    2. Take the bus from Bramalea GO Bus 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
    16h 30m

  8. 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 5m
    $325–637

Pickering to Chicago by bus and foot

Calendar5Weekly Services
Duration15h 56mAverage Duration
Ticket$83Cheapest Price
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Comparing Your Travel Options

Map of how to get from Pickering to Chicago.ExpandLaunch map view
  • Distance: 495.5 mi
  • Duration: 6h 12m

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

You can take a bus from Taunton Westbound @ Whites to Chicago Union Station via Pickering Parkway Terminal Platform B12, Pickering GO, Toronto Union Station, Windsor, and Detroit in around 13h. 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 56m.

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