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How to get fromNorth York to Chicagoby subway, plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus, or bus (Flixbus, Amtrak)

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There are 10 ways to get from North York to Chicago by subway, plane, train (Amtrak), bus (Flixbus, Greyhound), car, bus, 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 1 subway to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the subway from North York Centre Station - Southbound Platform to Union Station - Northbound Platform Towards Vaughan Metropolitan Centresubway subway
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 50m
    $374–957

  2. Fly Toronto Pearson International Airport to Chicago Midway International Airport

    cheapest
    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    7h 19m
    $54–327

  3. Train via Detroit

    1. Take the train from Toronto Union Station to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    12h 4m
    $213–455

  4. Bus

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    15h 19m
    $85–141

  5. Drive  509.7 mi

    1. Drive from North York to Chicagocar car 509.7 mi
    8h 31m
    $117–169

  6. Line 1 subway to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the subway from North York Centre Station - Southbound Platform to King Station - Southbound Platformsubway subway
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 40m
    $204–1,507

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

    1. Take the bus from Toronto to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    9h 28m
    $185–373

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

    1. Take the bus from Toronto to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    9h 53m
    $195–363

  9. Bus via Kitchener

    1. Take the bus from Hwy 407 Bus Terminal to Kitchener GO Busbus bus 30
    2. Take the bus from Kitchener to Detroit Bus Stationbus bus
    3. Take the bus from Dearborn to Chicago Union Stationbus bus
    16h 56m

  10. Train

    1. Take the train from Toronto Union Station to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    17h 5m
    $322–632

North York to Chicago by bus and foot

Calendar5Weekly Services
Duration15h 19mAverage Duration
Ticket$85Cheapest Price
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Comparing Your Travel Options

Map of how to get from North York to Chicago.ExpandLaunch map view
  • Distance: 478.4 mi
  • Duration: 5h 50m

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

You can take a subway from North York Centre Station - Southbound Platform to Chicago Union Station via Union Station - Northbound Platform Towards Vaughan Metropolitan Centre, Toronto Union Station, Windsor, and Detroit in around 12h 4m. Alternatively, you can take a bus from Yonge St. @ Park Home Ave. to Chicago Bus Station via Square One, Mississauga, and Detroit Bus Station in around 15h 19m.

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