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

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

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 5m
    $336–1,110

  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 10m
    $75–142

  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
    $146–409

  4. Drive 498.1 mi

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

  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 36m
    $178–1,313

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

    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
    5h 27m
    $148–433

  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 11m
    $256–560

  8. 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 26m
    $486–960

  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 34m
    $246–430

  10. Bus via Detroit

    1. Take the bus from Mississauga to Detroit Bus Stationbus bus FlixBus N2706
    2. Take the bus from Detroit to Chicago Union Stationbus bus Amtrak Thruway Connecting Service
    13h 22m
    $135–207

  11. 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
    $200–526

Mississauga to Chicago by bus, train, and car

Calendar21Weekly Services
Duration11h 53mAverage Duration
Ticket$146Cheapest Price
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Questions & Answers

Map of how to get from Mississauga to Chicago.ExpandLaunch map view
  • Distance: 464.2 mi
  • Duration: 5h 5m

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 53m.

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