Rome2Rio

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

Find Transport to Chicago

See all options

There are 8 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 WindsortrainVIA Rail
    2. Take the train from Detroit to Chicago Union StationtrainWolverine
    10h 13m
    $109–267

  2. Bus

    cheapest
    1. Take the bus from King St. W. @ Summers Ln. to Square Onebus40 / ...
    2. Take the bus from Mississauga to Detroit Bus Stationbus
    3. Take the bus from Detroit Bus Station to Chicago Bus Stationbus
    15h 59m
    $80–197

  3. Drive 466.1 mi

    1. Drive from Ancaster to Chicagocar466.1 mi
    7h 40m
    $107–155

  4. 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
    2. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    6h 58m
    $183–449

  5. 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
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    8h 12m
    $203–739

  6. 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
    2. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    3. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    8h 32m
    $178–579

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

    1. Take the train from West Harbour GO to Exhibition GOtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    7h 48m
    $142–458

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

    1. Take the train from West Harbour GO to Exhibition GOtrain
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    7h 59m
    $202–498

Ancaster to Chicago by bus and foot

Calendar5Weekly Services
Duration15h 59mAverage Duration
Ticket$80Cheapest Price
See schedules

Questions & Answers

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 bus from WILSON at ROUSSEAUX to Chicago Bus Station via MAIN at HUGHSON, King St. W. @ Summers Ln., Square One, Mississauga, and Detroit Bus Station in around 15h 59m.

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

More Questions & Answers

Where to next?

Trips from Ancaster

Trips to Chicago

Popular routes