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

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There are 10 ways to get from Waterloo to Chicago by bus, plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, shuttle, 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. Bus to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    best
    1. Take the bus from Kitchener to Toronto Pearson Airportbus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    5h 35m
    $390–1,017

  2. Bus

    cheapest
    1. Take the bus from Kitchener to Detroit Bus Stationbus bus FlixBus N2710
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    12h 25m
    $68–125

  3. Train

    1. Take the train from Kitchener to Sarniatrain train VIA Rail
    2. Take the train from Port Huron Station to Chicago Union Stationtrain train Blue Water
    10h 47m
    $118–377

  4. Drive 446.5 mi

    1. Drive from Waterloo to Chicagocar car 446.5 mi
    7h 56m
    $103–148

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

    1. Take the train from Kitchener 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 37m
    $185–1,321

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

    1. Take the bus from Kitchener to Toronto Pearson Airportbus bus
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    6h 41m
    $260–447

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

    1. Take the bus from Kitchener to Toronto Pearson Airportbus bus
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle bus
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    7h 9m
    $270–437

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

    1. Drive from Waterloo to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    6h 42m
    $94–353

  9. Bus, shuttle to Detroit, fly to Chicago Midway International Airport

    1. Take the bus from Kitchener to Londonbus bus
    2. Take a shuttle bus from Days Inn by Wyndham London to Detroit Airportshuttle bus
    3. Fly from Detroit (DTW) to Chicago Midway International Airport (MDW)plane plane DTW - MDW
    8h 25m
    $186–574

  10. Bus via Detroit

    1. Take the bus from Kitchener to Detroit Bus Stationbus bus FlixBus N2710
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    12h 37m
    $113–165

Waterloo to Chicago by train and car

Calendar7Weekly Services
Duration10h 47mAverage Duration
Ticket$118Cheapest Price
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Questions & Answers

Map of how to get from Waterloo to Chicago.ExpandLaunch map view
  • Distance: 508.7 mi
  • Duration: 5h 35m

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

You can take a train from Kitchener to Chicago Union Station via Sarnia and Port Huron Station in around 10h 47m. Alternatively, you can take a bus from Kitchener to Chicago Bus Station via Detroit Bus Station in around 12h 25m.

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