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

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There are 9 ways to get from Ancaster to Chicago by train (Amtrak), bus (Flixbus, Greyhound), car, bus, plane, shuttle, or train

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

    best
    1. Take the train from Aldershot to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    10h 13m
    $168–421

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

    cheapest
    1. Drive from Ancaster to Erie-Airport-ERIcar car
    2. Fly from Erie International Airport (ERI) to Chicago O'Hare International Airport (ORD)plane plane ERI - ORD
    5h 40m
    $81–331

  3. Bus

    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
    15h 8m
    $135–213

  4. Drive 466.1 mi

    1. Drive from Ancaster to Chicagocar car 466.1 mi
    7h 45m
    $107–155

  5. Bus to Toronto Pearson International Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from King St. W. @ Summers Ln. to Pearson International Airport Terminal 1bus bus
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)plane plane YYZ - ORD
    6h 54m
    $343–1,018

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

    1. Take the bus from King St. W. @ Summers Ln. to Pearson International Airport Terminal 1bus 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
    8h 1m
    $263–508

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

    1. Take the bus from King St. W. @ Summers Ln. to Pearson International Airport Terminal 1bus 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
    8h 23m
    $273–438

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

    1. Take the train from West Harbour GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    8h 3m
    $189–1,325

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

    1. Take the train from West Harbour GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    7h 54m
    $159–415

Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) flights

Calendar123Weekly Planes
Duration2h 2mAverage Duration
Ticket$41Cheapest Price
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Questions & Answers

Map of how to get from Ancaster to Chicago.ExpandLaunch map view
  • Distance: 486.5 mi
  • Duration: 10h 13m

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

You can take a vehicle from Ancaster to Chicago Union Station via Aldershot, Windsor, and Detroit in around 10h 13m. Alternatively, you can take a vehicle from Ancaster to Chicago Bus Station via Ainslie Terminal, Fairway Station, Victoria / Duke, Kitchener, and Detroit Bus Station in around 15h 8m.

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