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

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There are 10 ways to get from Whitby to Chicago by train, plane, train (Amtrak), bus, car, shuttle, or bus (Flixbus, Greyhound)

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

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

    best
    1. Take the train from Whitby GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 56m
    $190–1,515

  2. Bus

    cheapest
    1. Take the bus from Pickering GO Bus to Pearson International Airport Terminal 1bus bus 94
    2. Take the bus from Toronto Pearson Airport to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    16h 47m
    $84–161

  3. Train via Detroit

    1. Take the train from Whitby 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
    12h 36m
    $144–393

  4. Train, bus

    1. Take the train from Whitby GO to Union Station GOtrain train Le
    2. Take the bus from Toronto to Detroit Bus Stationbus bus
    3. Take the bus from Dearborn to Chicago Union Stationbus bus
    16h 11m
    $125–192

  5. Drive  537.7 mi

    1. Drive from Whitby to Chicagocar car 537.7 mi
    9h 5m
    $124–178

  6. Train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Whitby GO to Union Station GOtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 15m
    $380–1,115

  7. Train, shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the train from Whitby GO to Union Station GOtrain train
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 21m
    $260–445

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

    1. Take the train from Whitby GO to Union Station GOtrain train
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 38m
    $270–435

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

    1. Take the train from Whitby 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
    10h 31m
    $144–659

  10. Train

    1. Take the train from Whitby 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 37m
    $178–500

Whitby to Chicago by train and car

Calendar21Weekly Services
Duration12h 36mAverage Duration
Ticket$144Cheapest Price
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Questions & Answers

Map of how to get from Whitby to Chicago.ExpandLaunch map view
  • Distance: 497.9 mi
  • Duration: 5h 56m

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

You can take a train from Whitby GO to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 12h 36m. Alternatively, you can take a bus from Dundas Westbound @ Brock Street to Chicago Bus Station via Pickering Parkway Terminal Platform B12, Pickering GO Bus, Pearson International Airport Terminal 1, Toronto Pearson Airport, and Detroit Bus Station in around 16h 47m.

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