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How to get fromMississauga to Chicagoby 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 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)plane plane YYZ - ORD
    5h 7m
    $186–470

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

    cheapest
    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    6h 36m
    $61–350

  3. Train via Detroit

    1. Take the train from Oakville to Windsortrain train VIA Rail
    2. Take the train from Detroit to Chicago Union Stationtrain train Wolverine
    11h 56m
    $76–194

  4. Bus

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit Bus Station to Chicago Bus Stationbus bus Greyhound US0160
    13h 10m
    $69–152

  5. Drive 498.1 mi

    1. Drive from Mississauga to Chicagocar car 498.1 mi
    8h 24m
    $114–165

  6. 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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago O'Hare International Airport (ORD)plane plane BUF - ORD
    6h 47m
    $176–620

  7. 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 bus
    2. Fly from Buffalo Niagara International Airport (BUF) to Chicago Midway International Airport (MDW)plane plane BUF - MDW
    6h 36m
    $206–880

  8. 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 train
    2. Take the tram from Toronto Union Station to Fleet St at Bathurst St West Sidetram tram
    3. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 57m
    $201–486

  9. 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 train
    2. Take the tram from Toronto Union Station to Fleet St at Bathurst St West Sidetram tram
    3. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    5h 47m
    $121–476

  10. Train

    1. Take the train from Oakville to Buffalotrain train VIA Rail
    2. Take the train from Buffalo Depew Station to Chicago Union Stationtrain train Lake Shore Limited
    16h 57m
    $91–291

Mississauga to Chicago by bus, train, and car

Calendar21Weekly Services
Duration11h 56mAverage Duration
Ticket$76Cheapest Price
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Questions & Answers

What companies run services between Mississauga, ON, Canada and Chicago, 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 56m.

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Need to know: Greyhound

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