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

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There are 12 ways to get from Milton to Chicago by plane, bus, train, bus (Flixbus, Greyhound), car, shuttle, 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
    $345–1,123

  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 25m
    $77–145

  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
    $134–398

  4. Drive 483 mi

    1. Drive from Milton to Chicagocar car 483 mi
    8h 6m
    $111–160

  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 1m
    $180–1,315

  6. 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 6m
    $265–573

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

    1. Take the train from Milton GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    5h 52m
    $150–435

  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 29m
    $255–443

  9. Drive to Erie International Airport, fly to Chicago O'Hare International Airport

    1. Drive from Milton to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    5h 47m
    $83–324

  10. 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
    $159–413

  11. Bus via Detroit

    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 to Chicago Union Stationbus bus
    13h 37m
    $137–210

  12. 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 54m
    $200–525

Milton to Chicago by train and car

Calendar21Weekly Services
Duration12h 41mAverage Duration
Ticket$159Cheapest Price
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Questions & Answers

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

What companies run services between Milton, 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 bus from Milton, ON - Carpool Lot to Chicago Bus Station via London, ON - VIA Rail, London, and Detroit Bus Station in around 13h 25m.

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