Rome2Rio

How to get fromChicago to Pickeringby plane, bus, train (Amtrak), bus (Amtrak, Flixbus), car, train, or shuttle

Find Transport to Pickering

See all options

There are 11 ways to get from Chicago to Pickering by plane, bus, train (Amtrak), bus (Amtrak, Flixbus), 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. Fly Chicago O'Hare International Airport to Toronto Pearson International Airport, bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ)plane plane ORD - YYZ
    2. Take the bus from Hwy 407 Bus Terminal to Brock Rd. @ Hwy. 407 Park & Ridebus bus
    6h 15m
    $287–1,326

  2. Train, bus

    cheapest
    1. Take the train from Van Buren St. to Gary Metro Centertrain train Ssl
    2. Take the bus from Gary Bus Station to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Kitchenerbus bus
    4. Take the bus from Kitchener GO Bus to Bramalea GO Busbus bus 30
    5. Take the bus from Bramalea GO Bus to Brock Rd. @ Hwy. 407 Park & Ridebus bus 56
    18h
    $130–227

  3. Train via Detroit

    1. Take the train from Chicago Union Station to Detroittrain train Wolverine
    2. Take the train from Windsor to Toronto Union Stationtrain train VIA Rail
    12h 26m
    $177–397

  4. Bus

    1. Take the bus from Chicago Union Station to Dearbornbus bus
    2. Take the bus from Detroit Bus Station to Mississaugabus bus
    3. Take the bus from Square One to Brock Rd. @ Hwy. 407 Park & Ridebus bus 56
    14h 55m
    $181–280

  5. Drive 857.1 km

    1. Drive from Chicago to Pickeringcar car 857.1 km
    9h 1m
    $170–245

  6. Fly Chicago O'Hare International Airport to Toronto Island Airport, train, line 112 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Island Airport (YTZ)plane plane ORD - YTZ
    2. Take the train from Union Station GO to Pickering GOtrain train
    3. Take the bus from Pickering Parkway Terminal Platform B12 to Peter Matthews Southbound @ Alexander Knoxbus bus
    6h 27m
    $296–1,623

  7. Fly Chicago Midway International Airport to Toronto Island Airport, train

    1. Fly from Chicago Midway International Airport (MDW) to Toronto Island Airport (YTZ)plane plane MDW - YTZ
    2. Take the train from Union Station GO to Pickering GOtrain train
    6h 10m
    $166–673

  8. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, shuttle, bus

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)plane plane MDW - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle bus
    3. Take the bus from Hwy 407 Bus Terminal to Brock Rd. @ Hwy. 407 Park & Ridebus bus
    7h 15m
    $377–1,686

  9. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, shuttle, bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)plane plane ORD - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle bus
    3. Take the bus from Hwy 407 Bus Terminal to Brock Rd. @ Hwy. 407 Park & Ridebus bus
    7h 43m
    $297–1,186

  10. Fly Chicago O'Hare International Airport to Erie International Airport, drive

    1. Fly from Chicago O'Hare International Airport (ORD) to Erie International Airport (ERI)plane plane ORD - ERI
    2. Drive from Erie-Airport-ERI to Pickeringcar car
    7h 36m
    $138–537

  11. Train

    1. Take the train from Chicago Union Station to Buffalo Depew Stationtrain train Lake Shore Limited
    2. Take the train from Buffalo to Toronto Union Stationtrain train VIA Rail
    17h 18m
    $253–583

Chicago to Pickering by train, car, and bus

Calendar21Weekly Services
Duration12h 26mAverage Duration
Ticket$177Cheapest Price
See schedules

Questions & Answers

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

You can take a train from Chicago Union Station to Peter Matthews Southbound @ Alexander Knox via Detroit, Windsor, Union Station GO, Pickering GO, and Pickering Parkway Terminal Platform B12 in around 12h 26m. Alternatively, you can take a bus from Chicago Union Station to Brock Rd. @ Hwy. 407 Park & Ride via Dearborn Transit Center, Cass & Michigan, Rosa Parks Transit Center - Bay 10, Lafayette & Fifth, Detroit Bus Station, Mississauga, and Square One in around 14h 55m.

Airlines
Train operators
Bus operators

Want to know more about travelling around Canada

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers

Trips from Chicago

Trips to Pickering

Popular routes