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

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There are 9 ways to get from Port Perry to Chicago by bus, train, plane, bus (Flixbus, Greyhound), train (Amtrak), car, 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 905 bus, train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Simcoe Southbound @ Vanedward to Whitby Stationbus bus
    2. Take the train from Whitby GO to Union Station GOtrain train
    3. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    7h 28m
    $191–517

  2. Bus

    cheapest
    1. Take the bus from Simcoe St. N. @ Windfields Farm Dr. 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
    17h 20m
    $76–161

  3. 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
    18h 47m
    $172–407

  4. Drive 551.6 mi

    1. Drive from Port Perry to Chicagocar car 551.6 mi
    9h 26m
    $127–183

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

    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
    7h 8m
    $221–567

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

    1. Take the train from Whitby GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    6h 58m
    $111–767

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

    1. Take the bus from Simcoe St. N. @ Windfields Farm Dr. to Richmond Hill Centrebus bus
    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
    8h 42m
    $216–893

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

    1. Take the bus from Simcoe St. N. @ Windfields Farm Dr. to Richmond Hill Centrebus bus
    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
    9h 6m
    $176–573

  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
    11h 53m
    $160–781

Port Perry to Chicago by bus and foot

Calendar5Weekly Services
Duration17h 20mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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

You can take a bus from Curts Eastbound @ Port Perry Terminal to Chicago Bus Station via Simcoe Southbound @ Windfields Farm, Simcoe St. N. @ Windfields Farm Dr., Square One, Mississauga, and Detroit Bus Station in around 17h 20m. Alternatively, you can take a bus from Simcoe Southbound @ Vanedward to Chicago Union Station via Whitby Station, Whitby GO, Toronto Union Station, and Buffalo Depew Station in around 18h 47m.

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