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Flights from Toronto to Chicago – Airlines & connecting routes

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YYZ to MDW flights and routes map YYZ to MDW – All flight route options from Pearson International, Canada to Chicago Midway International, Illinois, USA. These flights are operated by 4 different airlines through 1 different connections. The shortest flight time is 3 hours and 45 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
Canada YYZ Pearson Toronto, ON, Canada
USA MDW Chicago Midway , IL, USA
YYZ
Pearson
CanadaToronto, ON, Canada
Chicago Midway
USAChicago, IL, USA
MDW
No direct flights found
2 routes with 1 stop found »
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1 stop route options with the same airline:

Duration

Via Detroit DTW
1 stop with Delta Air Lines. 4 flights per day.

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3h 45m

Via Detroit DTW
1 stop with Delta Air Lines.
3h 45m
4 flights per day.
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1 stop route options with codeshare or different airlines:

Duration

Via Detroit DTW With Air Canada & Delta Air Lines 0-1 flights per day.

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5h 26m

Via Detroit DTW
5h 26m
With Air Canada & Delta Air Lines 0-1 flights per day.
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Other flight options

Check out these routes. They have daily flights from Pearson International and connections to Chicago:

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Toronto to Chicago flights

This route is operated by one airline and has approximately 96 flights per week. You will be doing a stopover in Detroit (Airport code: DTW).

Are there any non-stop flights from YYZ to MDW?

There are no direct or non-stop flights from Pearson International, YYZ to Chicago Midway International, MDW.

Toronto to Chicago with Delta Air Lines

If you fly from Toronto with Delta Air Lines you will do a stopover in Detroit, DTW before reaching Chicago. This flight trip will take 3 hours and 45 minutes and you can fly every weekday with departures between 6:00 am and 4:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Pearson to Midway International Airport

The flight time between YYZ and MDW is 5 hours and 26 minutes.

ViaTotal flight timeLayover timeDistance
DTW Detroit5h 26m2h 24m443 miles (713 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.
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Toronto - Chicago route map and flight paths
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Show all destinations from YYZ Show all destinations from MDW
From Toronto to USA

Below is a list of other destinations to USA from Pearson International with either direct flights or 1 stop connections.

From Canada to Chicago

Below is a list of other cities in Canada with flights to Chicago with either non-stop or connecting flights.

Via Detroit. A flight from Toronto (YYZ) to Chicago (MDW) via Detroit will take approximately 5 hours and 26 minutes.

You can fly with Air Canada or Delta Air Lines from Toronto to Chicago.

The flight time between Pearson (YYZ) and Chicago Midway International (MDW) via Detroit Metropolitan Airport, DTW is 5 hours and 26 minutes.

No. But you can still purchase a 1 stop flight via Detroit to Chicago (MDW).

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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