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How to get fromDowntown Toronto to Chicago Loopby plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle or train

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There are 10 ways to get from Downtown Toronto to Chicago Loop by plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, or train

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

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

    best
    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 7m
    $183–416

  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
    14h 14m
    $71–153

  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
    $113–279

  4. Drive 514.1 mi

    1. Drive from Downtown Toronto to Chicago Loopcar car 514.1 mi
    8h 37m
    $118–170

  5. 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 49m
    $212–555

  6. 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 45m
    $102–805

  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 23m
    $206–821

  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
    6h 39m
    $161–541

  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
    8h 49m
    $147–721

  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
    15h 39m
    $164–415

Downtown Toronto to Chicago Loop by train and car

Calendar21Weekly Services
Duration10h 38mAverage Duration
Ticket$113Cheapest Price
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Questions & Answers

What companies run services between Downtown Toronto, ON, Canada and Chicago Loop, IL, USA?

American Airlines, Air Canada, and two other airlines fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a train from Toronto Union Station to Chicago Union Station via Windsor and Detroit in around 10h 38m.

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