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

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There are 11 ways to get from Milton to Chicago by bus, plane, train, bus (Flixbus, Greyhound), car, shuttle, or train (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 25 bus to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Regional Rd. 25 @ Hwy. 401 Park & Ride to Square Onebus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    5h 54m
    $182–447

  2. Bus, train

    cheapest
    1. Take the bus from Milton, ON - Carpool Lot to London, ON - VIA Railbus
    2. Take the train from London to Sarniatrain
    3. Take the train from Port Huron Station to Chicago Union Stationtrain
    11h 27m
    $66–228

  3. Bus

    1. Take the bus from Milton, ON - Carpool Lot to London, ON - Victoria Hospitalbus
    2. Take the bus from London to Detroit Bus Stationbus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    13h 54m
    $72–183

  4. Drive 483 mi

    1. Drive from Milton to Chicagocar483 mi
    8h 2m
    $111–160

  5. Train to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the train from Milton GO to Toronto Union Stationtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    6h
    $133–448

  6. Fly Toronto Pearson International Airport to Chicago Midway International Airport

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)planeYYZ - MDW
    7h 48m
    $352–867

  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
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    7h 8m
    $202–737

  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
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    7h 28m
    $177–577

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

    1. Take the train from Milton GO to Toronto Union Stationtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    6h 11m
    $193–488

  10. Train via Detroit

    1. Take the train from Milton GO to Toronto Union StationtrainMi
    2. Take the train from Toronto Union Station to Windsortrain
    3. Take the train from Detroit to Chicago Union Stationtrain
    12h 41m
    $89–243

  11. Train

    1. Take the train from Oakville to BuffalotrainVIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union StationtrainLake Shore Limited
    16h 54m
    $91–291

Milton to Chicago by train and car

Calendar21Weekly Services
Duration12h 41mAverage Duration
Ticket$89Cheapest Price
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Questions & Answers

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

You can take a bus from Milton, ON - Carpool Lot to Chicago Bus Station via London, ON - Victoria Hospital, Wellington South of Baseline NB - #1923, Elgin Hall WB - #1821, London, and Detroit Bus Station in around 13h 54m. Alternatively, Delta, Air Canada, and two other airlines fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW) 5 times a day.

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