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

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There are 10 ways to get from Toronto (Station) to Chicago by 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. 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 15m
    $398–982

  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
    6h 34m
    $51–300

  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 43m
    $135–408

  4. Bus

    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
    $77–131

  5. Drive  509.5 mi

    1. Drive from Toronto (Station) to Chicagocar car 509.5 mi
    8h 35m
    $117–169

  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
    5h 7m
    $202–1,405

  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
    7h 56m
    $183–369

  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
    8h 21m
    $193–359

  9. Bus via Dearborn

    1. Take the bus from Toronto to Detroit Bus Stationbus bus FlixBus 2701 / ...
    2. Take the bus from Dearborn to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    14h 13m
    $104–153

  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 43m
    $171–539

Toronto (Station) to Chicago by foot, train, and car

Calendar21Weekly Services
Duration10h 43mAverage Duration
Ticket$135Cheapest Price
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Comparing Your Travel Options

Map of how to get from Toronto (Station) to Chicago.ExpandLaunch map view
  • Distance: 469.6 mi
  • Duration: 5h 15m

What companies run services between Toronto (Station), ON, Canada and Chicago, IL, USA?

American Airlines, Air Canada, and United Airlines fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a vehicle from Toronto (Station) to Chicago Union Station via Toronto Union Station, Windsor, and Detroit in around 10h 43m.

Airlines
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Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

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