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

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There are 11 ways to get from North York to Chicago by subway, plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, train, 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 Island Airport, fly to Chicago O'Hare International Airport

    best
    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 29m
    $174–1,307

  2. Bus

    cheapest
    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
    $86–152

  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
    $153–405

  4. Drive 512.9 mi

    1. Drive from North York to Chicagocar car 512.9 mi
    8h 38m
    $118–170

  5. Line 1 subway to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    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 43m
    $334–1,107

  6. Line 1 subway to Toronto Island Airport, fly to Chicago Midway 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 Midway International Airport (MDW)plane plane YTZ - MDW
    5h 20m
    $144–427

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

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    6h 49m
    $254–557

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

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 12m
    $244–427

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

    1. Take the train from Toronto Union Station to Rochestertrain train
    2. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    9h 59m
    $143–651

  10. Bus via Detroit

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    15h 32m
    $136–207

  11. 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
    $202–532

North York to Chicago by subway, train, and car

Calendar21Weekly Services
Duration12h 4mAverage Duration
Ticket$153Cheapest Price
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Questions & Answers

Map of how to get from North York to Chicago.ExpandLaunch map view
  • Distance: 474.7 mi
  • Duration: 5h 29m

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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