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

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There are 10 ways to get from Milton to Chicago by plane, bus, train, bus (Flixbus, Greyhound), car, train (Amtrak), 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 2m
    $405–972

  2. Bus

    cheapest
    1. Take the bus from Milton, ON - Carpool Lot to London, ON - VIA Railbus bus
    2. Take the bus from London to Detroit Bus Stationbus bus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    13h 40m
    $77–123

  3. Bus, train

    1. Take the bus from Milton, ON - Carpool Lot to London, ON - VIA Railbus bus
    2. Take the train from London to Sarniatrain train
    3. Take the train from Port Huron Station to Chicago Union Stationtrain train
    11h 27m
    $109–367

  4. Drive  479.8 mi

    1. Drive from Milton to Chicagocar car 479.8 mi
    8h 2m
    $110–159

  5. Train to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Milton GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    6h 3m
    $190–1,415

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

    1. Take the bus from Mississauga to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    7h 54m
    $187–380

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

    1. Take the bus from Mississauga to Buffalobus bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    8h 13m
    $197–370

  8. Train via Detroit

    1. Take the train from Milton GO to Union Station GOtrain train Mi
    2. Take the train from Toronto Union Station to Windsortrain train
    3. Take the train from Detroit to Chicago Union Stationtrain train
    12h 41m
    $129–393

  9. Bus via Dearborn

    1. Take the bus from Milton, ON - Carpool Lot to London, ON - VIA Railbus bus
    2. Take the bus from London to Detroit Bus Stationbus bus
    3. Take the bus from Dearborn to Chicago Union Stationbus bus
    13h 58m
    $99–150

  10. Train

    1. Take the train from Oakville to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    16h 59m
    $150–485

Milton to Chicago by train and car

Calendar21Weekly Services
Duration12h 41mAverage Duration
Ticket$129Cheapest Price
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Comparing Your Travel Options

Map of how to get from Milton to Chicago.ExpandLaunch map view
  • Distance: 475.8 mi
  • Duration: 5h 2m

What companies run services between Milton, ON, Canada and Chicago, 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 bus from Milton, ON - Carpool Lot to Chicago Bus Station via London, ON - VIA Rail, London, and Detroit Bus Station in around 13h 40m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

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