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

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There are 11 ways to get from Ontario to Chicago by car, plane, train (Amtrak), bus (Flixbus, Greyhound), 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. Drive to Detroit, fly to Chicago Midway International Airport

    best
    1. Drive from Windsor to Michigan & Casscar car
    2. Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane plane DTW - MDW
    3h 56m
    $135–468

  2. Bus

    cheapest
    1. Take the bus from Toronto to Detroit Bus Stationbus bus FlixBus 2701 / ...
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160 / ...
    13h 55m
    $108–177

  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
    10h 38m
    $151–402

  4. Drive 513.5 mi

    1. Drive from Toronto to Chicagocar car 513.5 mi
    8h 37m
    $118–170

  5. Fly Detroit to Chicago O'Hare International Airport

    1. Fly from Detroit (DTW) to Chicago O'Hare International Airport (ORD)plane plane DTW - ORD
    4h 15m
    $155–658

  6. Fly Toronto Island Airport to Chicago O'Hare International Airport

    1. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    4h 50m
    $172–1,305

  7. Fly Toronto Pearson International Airport to Chicago O'Hare International Airport

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 8m
    $335–1,065

  8. Fly Toronto Island Airport to Chicago Midway International Airport

    1. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    4h 41m
    $142–435

  9. Fly Ottawa Macdonald-Cartier International Airport to Chicago O'Hare International Airport

    1. Fly from Ottawa Macdonald-Cartier International Airport (YOW) to Chicago O'Hare International Airport (ORD)plane plane YOW - ORD
    5h 50m
    $305–1,208

  10. Bus via Detroit

    1. Take the bus from Toronto to Detroit Bus Stationbus bus FlixBus 2701 / ...
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    14h 7m
    $158–227

  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
    15h 39m
    $201–522

Ontario to Chicago by train and car

Calendar21Weekly Services
Duration10h 38mAverage Duration
Ticket$151Cheapest Price
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Questions & Answers

Map of how to get from Ontario to Chicago.ExpandLaunch map view
  • Distance: 263.6 mi
  • Duration: 3h 56m

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

You can take a train from Toronto Union Station to Chicago Union Station via Windsor and Detroit in around 10h 38m. Alternatively, you can take a bus from Toronto to Chicago Bus Station via Detroit Bus Station in around 13h 55m.

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