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How to get fromPort Perry to Chicago Union Stationby bus, train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, subway or shuttle

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There are 10 ways to get from Port Perry to Chicago Union Station by bus, train, plane, train (Amtrak), bus (Flixbus, Greyhound), car, subway, 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 42m
    $201–517

  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 29m
    $70–152

  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
    13h 47m
    $105–265

  4. Drive 552.1 mi

    1. Drive from Port Perry to Chicago Union Stationcar car 552.1 mi
    9h 27m
    $127–183

  5. Line 905 bus, train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    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 Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    7h 42m
    $224–531

  6. Line 905 bus, train to Toronto Island Airport, fly to Chicago Midway International Airport, subway

    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 Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    4. Take the subway from Midway to Quincysubway subway
    7h 26m
    $144–581

  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
    8h 46m
    $221–937

  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
    9h 18m
    $171–587

  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
    12h 7m
    $160–786

  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
    18h 47m
    $142–372

Port Perry to Chicago Union Station by bus, train, and car

Calendar21Weekly Services
Duration13h 47mAverage Duration
Ticket$105Cheapest Price
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Questions & Answers

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

You can take a bus from Simcoe Southbound @ Vanedward to Chicago Union Station via Whitby Station, Whitby GO, Toronto Union Station, Windsor, and Detroit in around 13h 47m. Alternatively, you can take a bus from Curts Eastbound @ Port Perry Terminal to Chicago Union Station via Simcoe Southbound @ Windfields Farm, Simcoe St. N. @ Windfields Farm Dr., Square One, Mississauga, Detroit Bus Station, and Chicago Bus Station in around 17h 29m.

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