Rome2Rio

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

Find Transport to Chicago

See all options

There are 11 ways to get from Waterdown to Chicago by train (Amtrak), train, bus, car, plane, or bus (Flixbus, Greyhound)

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

  1. Train via Detroit

    best
    1. Take the train from Aldershot to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    11h 6m
    $204–446

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

    cheapest
    1. Drive from Waterdown to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    5h 58m
    $80–320

  3. Train, bus

    1. Take the train from Aldershot to Londontrain train
    2. Take the bus from London to Detroit Bus Stationbus bus
    3. Take the bus from Dearborn to Chicago Union Stationbus bus
    15h 11m

  4. Drive  475.1 mi

    1. Drive from Waterdown to Chicagocar car 475.1 mi
    7h 59m
    $109–157

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

    1. Take the train from Aldershot 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 56m
    $211–1,516

  6. Train

    1. Take the train from Aldershot to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    16h 10m
    $314–613

  7. Bus

    1. Take the bus from Aldershot GO Bus to Guelph Central GO Busbus bus 17
    2. Take the bus from Guelph to Londonbus bus
    3. Take the bus from London to Detroit Bus Stationbus bus
    4. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus
    17h 47m
    $86–140

  8. Train to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Aldershot GO to Union Station GOtrain train
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    7h 10m
    $381–966

  9. Train, bus to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take the train from Aldershot to Canadian Bordertrain train
    2. Take the bus from Niagara Falls to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    8h 51m
    $205–398

  10. Train, bus to Buffalo Niagara International Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Aldershot to Canadian Bordertrain train
    2. Take the bus from Niagara Falls to Buffalobus bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    9h 16m
    $215–388

  11. Train to Rochester, fly to Chicago Midway International Airport

    1. Take the train from Aldershot to Rochestertrain train
    2. Fly from Rochester (ROC) to Chicago Midway International Airport (MDW)plane plane ROC - MDW
    9h 14m
    $144–762

Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD) flights

Calendar28Weekly Planes
Duration2h 53mAverage Duration
Ticket$42Cheapest Price
See schedules

Comparing Your Travel Options

Map of how to get from Waterdown to Chicago.ExpandLaunch map view
  • Distance: 477.8 mi
  • Duration: 11h 6m

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

You can take a bus from DUNDAS at MAIN to Chicago Union Station via Aldershot Go Via Station Platform 10, Aldershot, Windsor, and Detroit in around 11h 6m. Alternatively, you can take a bus from DUNDAS at HAMILTON to Chicago Bus Station via Aldershot Go Via Station Platform 10, Aldershot GO Bus, Guelph Central GO Bus, Guelph, London, and Detroit Bus Station in around 17h 47m.

Airlines
Train operators
Bus operators

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

Read the travel guideNeed to know: Greyhound

Booking & Getting There