YYZ - MDW

C$ 185 Find Cheap Flights from Toronto Pearson Airport to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pearson Intl to Midway departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Pearson Intl to Midway (YYZ-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Pearson Intl to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Pearson Intl to Midway

Sat, 13 Sep - Sat, 20 Sep
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
Delta Logo
6:15 p.m. - 10:56 p.m.MDW-YYZ
3h 41m1 stop
C$ 292Delta
Find Deal
Thu, 25 Sep - Mon, 29 Sep
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
Delta Logo
9:35 a.m. - 5:23 p.m.MDW-YYZ
6h 48m1 stop
C$ 294Delta
Find Deal
Fri, 5 Sep - Tue, 16 Sep
Delta Logo
12:15 p.m. - 6:37 p.m.YYZ-MDW
7h 22m1 stop
Delta Logo
9:35 a.m. - 5:23 p.m.MDW-YYZ
6h 48m1 stop
C$ 310Delta
Find Deal
Wed, 27 Aug - Fri, 5 Sep
Delta Logo
6:30 a.m. - 12:28 p.m.YYZ-MDW
6h 58m1 stop
Delta Logo
9:30 a.m. - 5:23 p.m.MDW-YYZ
6h 53m1 stop
C$ 327Delta
Find Deal
Fri, 12 Sep - Fri, 19 Sep
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
Delta Logo
9:29 a.m. - 5:23 p.m.MDW-YYZ
6h 54m1 stop
C$ 328Delta
Find Deal
Thu, 4 Sep - Mon, 8 Sep
Delta Logo
6:30 a.m. - 8:35 a.m.YYZ-MDW
3h 05m1 stop
Delta Logo
1:43 p.m. - 11:33 p.m.MDW-YYZ
8h 50m1 stop
C$ 331Delta
Find Deal
Thu, 28 Aug - Thu, 4 Sep
Delta Logo
6:30 a.m. - 12:28 p.m.YYZ-MDW
6h 58m1 stop
Delta Logo
9:30 a.m. - 5:23 p.m.MDW-YYZ
6h 53m1 stop
C$ 332Delta
Find Deal
Thu, 4 Sep - Sun, 7 Sep
Delta Logo
6:30 a.m. - 8:35 a.m.YYZ-MDW
3h 05m1 stop
Delta Logo
9:31 a.m. - 5:23 p.m.MDW-YYZ
6h 52m1 stop
C$ 342Delta
Find Deal
Thu, 4 Sep - Mon, 8 Sep
WestJet Logo
1:20 p.m. - 9:26 p.m.YYZ-MDW
9h 06m1 stop
WestJet Logo
10:31 a.m. - 4:57 p.m.MDW-YYZ
5h 26m1 stop
C$ 386WestJet
Find Deal
Tue, 7 Oct - Tue, 21 Oct
WestJet Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
WestJet Logo
1:48 p.m. - 11:18 p.m.MDW-YYZ
8h 30m1 stop
C$ 388WestJet
Find Deal
Booking Insights

KAYAK's insights & trends for Pearson Intl to Midway flights

Get data-powered insights and trends into flights from Pearson Intl to Midway to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

What is the cheapest month to fly from Toronto Pearson Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto Pearson Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Toronto Pearson Intl Airport to Chicago Midway Airport is February, where tickets cost C$ 302 (return) on average. On the other hand, the most expensive months are August and October, where the average cost of round-trip tickets is C$ 560 and C$ 520 respectively.


Good to know

Low seasonFebruary
Cheapest flightC$ 185
Best time to beat the crowds (29% less expensive on average)
Most popular time to fly (31% more expensive on average)
Flight from Toronto Pearson Airport to Chicago Midway Airport

When to book flights from Pearson Intl to Midway

Are your dates flexible? Find out the best times to travel from Pearson Intl to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Toronto Pearson Airport to Chicago Midway Airport flights

  • What is the cheapest flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Toronto Pearson Intl Airport to Chicago Midway Airport was C$ 134 for a one-way ticket and C$ 212 for a round-trip.

  • Which aircraft models fly most regularly from Toronto Pearson Airport to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Toronto Pearson Airport to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Toronto Pearson Airport and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Toronto Pearson Airport to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Toronto Pearson Airport to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Toronto Pearson Airport to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Toronto Pearson Airport is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Toronto Pearson Airport to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Toronto Pearson Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Pearson Airport to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Toronto Pearson Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Pearson Intl to Midway

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Pearson Intl to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 318 reviews
8.0Comfort
8.2Boarding
8.7Crew
7.0Entertainment
7.6Food
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

Staff were courteous and helpful. The only negative was the flight delays (which are usually unavoidable) and the high baggage price.

Absolutely terrible, from the customer service to boarding the plane. On the phone, there was some mishaps with getting in my correct date and they did not help me retrieve a refund or any assistance. I’m gonna be reporting to all my followers and family around the region of Los Angeles to New York.

Could not fly out of Canada. Called airlines on Monday, July 14th. Tried to cancel the flight 7 days away, but they said I could not cancel and there would be no refund.

A little disorganized but overall good. The Delta flights were great though

Price was good. Entertainment and food could have been better

Arrival at Comox from, London,ON 6 hours later... No bueano

Generally good. However. The flight left 30 mins behind schedule with no reason given.

Flight delayed, missed my pick-up had to Uber, plus missed dinner and medication, so sad!

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

Everything you need to know for your flight from Pearson Intl to Midway

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