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

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There are 10 ways to get from Mississauga to Chicago Loop by plane, train (Amtrak), bus (Flixbus, Greyhound), car, train, subway, 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 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 6m
    $186–510

  2. Bus

    cheapest
    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 24m
    $66–146

  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 53m
    $111–274

  4. Drive 499 mi

    1. Drive from Mississauga to Chicago Loopcar car 499 mi
    8h 25m
    $115–165

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

    1. Take the train from Erindale GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago O'Hare International Airport (ORD)plane plane YTZ - ORD
    5h 35m
    $218–563

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

    1. Fly from Toronto Pearson International Airport (YYZ) to Chicago Midway International Airport (MDW)plane plane YYZ - MDW
    6h 52m
    $366–910

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

    1. Take the train from Erindale GO to Union Station GOtrain train
    2. Fly from Toronto Island Airport (YTZ) to Chicago Midway International Airport (MDW)plane plane YTZ - MDW
    3. Take the subway from Midway to Washington/Wellssubway subway
    5h 31m
    $108–763

  8. 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 22m
    $206–880

  9. 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 38m
    $166–560

  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 54m
    $165–401

Mississauga to Chicago Loop by bus, train, and car

Calendar21Weekly Services
Duration11h 53mAverage Duration
Ticket$111Cheapest 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 two other 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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