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How to get fromToronto to Chicagoby taxi, plane, train, bus, or car

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There are 7 ways to get from Toronto to Chicago by taxi, plane, train, bus, or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

  1. Taxi to Pittsburgh International Airport, fly to Chicago Midway International Airport

    best
    1. Take the taxi from Toronto to Pittsburgh-Airport-PITtaxi taxi
    2. Fly from Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW)plane plane PIT - MDW
    2h 43m
    $130–445

  2. Drive to Akron, fly to Chicago O'Hare International Airport

    cheapest
    1. Drive from Toronto to Akron-Airport-CAKcar car
    2. Fly from Akron (CAK) to Chicago O'Hare International Airport (ORD)plane plane CAK - ORD
    4h 13m
    $54–283

  3. Taxi, train (Amtrak)

    1. Take the taxi from Toronto to Pittsburgh Amtrak Stationtaxi taxi
    2. Take the train from Pittsburgh Amtrak Station to Chicago Union Stationtrain train Floridian
    10h 43m
    $242–428

  4. Taxi, bus

    1. Take the taxi from Toronto to Pittsburgh International Airporttaxi taxi
    2. Take the bus from Pittsburgh Intermodal Station to Chicago Bus Stationbus bus Greyhound US0164
    12h 32m
    $138–220

  5. Drive 433.3 mi

    1. Drive from Toronto to Chicagocar car 433.3 mi
    7h 38m
    $80–115

  6. Taxi to Pittsburgh International Airport, fly to Chicago O'Hare International Airport

    1. Take the taxi from Toronto to Pittsburgh-Airport-PITtaxi taxi
    2. Fly from Pittsburgh International Airport (PIT) to Chicago O'Hare International Airport (ORD)plane plane PIT - ORD
    3h 10m
    $450–1,285

  7. Taxi, bus via Chicago (Flixbus)

    1. Take the taxi from Toronto to Pittsburgh International Airporttaxi taxi
    2. Take the bus from Pittsburgh Intermodal Station to Chicagobus bus FlixBus N2640
    13h 50m
    $155–235

Pittsburgh International Airport (PIT) to Chicago Midway International Airport (MDW) flights

Calendar22Weekly Planes
Duration1h 35mAverage Duration
Ticket$61Cheapest Price
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Questions & Answers

Map of how to get from Toronto to Chicago.ExpandLaunch map view
  • Distance: 443.5 mi
  • Duration: 2h 43m

What companies run services between Toronto, OH, USA and Chicago, IL, USA?

There is no direct connection from Toronto to Chicago. However, you can take the taxi to Pittsburgh-Airport-PIT airport, fly to Chicago Midway International Airport (MDW), walk to Midway, then take the subway to Harold Washington Library. Alternatively, you can take the taxi to Pittsburgh Amtrak Station then take the train to Chicago Union Station.

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