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How to get fromChicago to Caledonby plane, bus, train (Amtrak), bus (Greyhound, Flixbus), car, subway, train or shuttle

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

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 Chicago O'Hare International Airport to Toronto Pearson International Airport, line 37 bus

    best
    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Pearson International Airport (YYZ)planeORD - YYZ
    2. Take the bus from Brampton Bus Terminal to Hurontario St. @ Charleston Side Rd.bus
    7h 27m
    $249–627

  2. Train via Sarnia

    cheapest
    1. Take the train from Chicago Union Station to Port Huron StationtrainBlue Water
    2. Take the train from Sarnia to GeorgetowntrainVIA Rail
    14h 44m
    $96–309

  3. Train

    1. Take the train from Chicago Union Station to DetroittrainWolverine
    2. Take the train from Windsor to Toronto Union StationtrainVIA Rail
    13h 43m
    $138–360

  4. Bus

    1. Take the bus from Chicago Bus Station to Detroit Bus StationbusGreyhound US0160
    2. Take the bus from Detroit Bus Station to MississaugabusFlixBus N2706
    15h 27m
    $109–290

  5. Drive 799 km

    1. Drive from Chicago to Caledoncar799 km
    8h 37m
    $156–225

  6. Subway to Chicago Midway International Airport, fly to Toronto Island Airport, train, line 37 bus

    1. Take the subway from Roosevelt to Midwaysubway
    2. Fly from Chicago Midway International Airport (MDW) to Toronto Island Airport (YTZ)planeMDW - YTZ
    3. Take the train from Toronto Union Station to Brampton Innovation District GOtrain
    4. Take the bus from Brampton Bus Terminal to Hurontario St. @ Charleston Side Rd.bus
    7h 38m
    $182–631

  7. Fly Chicago Midway International Airport to Buffalo Niagara International Airport, shuttle

    1. Fly from Chicago Midway International Airport (MDW) to Buffalo Niagara International Airport (BUF)planeMDW - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle
    8h 26m
    $389–1,687

  8. Fly Chicago O'Hare International Airport to Toronto Island Airport, train, line 37 bus

    1. Fly from Chicago O'Hare International Airport (ORD) to Toronto Island Airport (YTZ)planeORD - YTZ
    2. Take the train from Toronto Union Station to Brampton Innovation District GOtrain
    3. Take the bus from Brampton Bus Terminal to Hurontario St. @ Charleston Side Rd.bus
    7h 54m
    $272–681

  9. Fly Chicago O'Hare International Airport to Buffalo Niagara International Airport, shuttle

    1. Fly from Chicago O'Hare International Airport (ORD) to Buffalo Niagara International Airport (BUF)planeORD - BUF
    2. Take a shuttle bus from Buffalo Airport to Pearson International Airport Terminal 1shuttle
    8h 57m
    $339–1,387

  10. Fly Chicago Midway International Airport to Toronto Pearson International Airport

    1. Fly from Chicago Midway International Airport (MDW) to Toronto Pearson International Airport (YYZ)planeMDW - YYZ
    8h 41m
    $489–1,127

  11. Train #2

    1. Take the train from Chicago Union Station to Buffalo Depew StationtrainLake Shore Limited
    2. Take the train from Buffalo to Toronto Union StationtrainVIA Rail
    18h 37m
    $122–417

Chicago to Caledon by train, car, and bus

Calendar21Weekly Services
Duration13h 43mAverage Duration
Ticket$138Cheapest Price
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Questions & Answers

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

You can take a train from Chicago Union Station to Hurontario St. @ Travelled Rd. via Detroit, Windsor, Toronto Union Station, Brampton Innovation District GO, and Brampton Bus Terminal in around 13h 43m. Alternatively, you can take a bus from Chicago Bus Station to Hurontario St. @ Charleston Side Rd. via Detroit Bus Station, Mississauga, City Centre Transit Terminal - Platform L, Theatre Lane - Zum Main Station Stop NB, and Brampton Bus Terminal in around 15h 27m.

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