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

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There are 11 ways to get from Pickering to Chicago by bus, plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, 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. 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
    $333–1,119

  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
    16h
    $80–147

  3. Train via Detroit

    1. Take the train from Pickering GO to Union Station GOtrain train Le
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    13h 4m
    $154–404

  4. Drive 532.1 mi

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

  5. Train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Pickering GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 23m
    $200–1,316

  6. Train to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the train from Pickering GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 14m
    $140–446

  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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 19m
    $193–689

  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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 46m
    $173–549

  9. Train, train to Rochester, fly to Chicago Midway International Airport

    1. Take the train from Pickering GO to Union Station GOtrain train
    2. Take the train from Toronto Union Station to Rochestertrain train
    3. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    11h 3m
    $149–690

  10. 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 Detroit to Chicago Union Stationbus bus
    16h 31m
    $140–212

  11. Train

    1. Take the train from Pickering GO to Union Station GOtrain train Le
    2. Take the train from Toronto Union Station to Buffalotrain train
    3. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train
    17h 56m
    $198–531

Pickering to Chicago by bus, train, and car

Calendar21Weekly Services
Duration13h 4mAverage Duration
Ticket$154Cheapest Price
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Questions & Answers

Map of how to get from Pickering to Chicago.ExpandLaunch map view
  • Distance: 495.9 mi
  • Duration: 6h 12m

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

You can take a bus from Peter Matthews Northbound @ Alexander Knox to Chicago Union Station via Pickering Parkway Terminal Platform B12, Pickering GO, Toronto Union Station, Windsor, and Detroit in around 13h 4m. 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 16h.

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