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How to get fromMississauga to Chicago Loopby plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, train or tram

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There are 10 ways to get from Mississauga to Chicago Loop by plane, train (Amtrak), bus (Flixbus, Greyhound), car, shuttle, train, or tram

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 Toronto Pearson International Airport to Chicago O'Hare International Airport

    best
    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD)planeYYZ - ORD
    5h 1m
    $166–760

  2. Bus

    cheapest
    1. Take the bus from Mississauga to Detroit Bus StationbusFlixBus N2706
    2. Take the bus from Detroit Bus Station to Chicago Bus StationbusGreyhound US0160
    13h 24m
    $72–139

  3. Train via Detroit

    1. Take the train from Oakville to WindsortrainVIA Rail
    2. Take the train from Detroit to Chicago Union StationtrainWolverine
    11h 53m
    $76–233

  4. Drive 499 mi

    1. Drive from Mississauga to Chicago Loopcar499 mi
    8h 21m
    $115–165

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

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)planeYYZ - MDW
    6h 51m
    $336–910

  6. Shuttle to Buffalo Niagara International Airport, fly to Chicago Midway International Airport

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)planeBUF - MDW
    6h 24m
    $196–720

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

    1. Take a shuttle bus from Pearson International Airport Terminal 1 to Buffalo Airportshuttle
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)planeBUF - ORD
    6h 37m
    $166–550

  8. Train, line 509 tram to Toronto Island Airport, fly to Chicago Midway International Airport

    1. Take the train from Erindale GO to Toronto Union Stationtrain
    2. Take the tram from Toronto Union Station to Fleet St at Bathurst St West Sidetram
    3. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)planeYTZ - MDW
    5h 50m
    $121–526

  9. Train, line 509 tram to Toronto Island Airport, fly to Chicago O'Hare International Airport

    1. Take the train from Erindale GO to Toronto Union Stationtrain
    2. Take the tram from Toronto Union Station to Fleet St at Bathurst St West Sidetram
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)planeYTZ - ORD
    5h 54m
    $201–456

  10. Train

    1. Take the train from Oakville to BuffalotrainVIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union StationtrainLake Shore Limited
    16h 54m
    $105–280

Mississauga to Chicago Loop by bus, train, and car

Calendar21Weekly Services
Duration11h 53mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

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

American Airlines, Air Canada, and United Airlines fly from Toronto Pearson International Airport (YYZ) to Chicago O'Hare International Airport (ORD) hourly. Alternatively, you can take a bus from Square One to Chicago Union Station via Oakville GO Bus, Oakville, Windsor, and Detroit in around 11h 53m.

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