YYZ - MDW

C$ 200 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 29/10. 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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Booking Insights
Flight 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, 18 Oct - Sat, 25 Oct
WestJet Logo
6:20 a.m. - 10:30 a.m.YYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
C$ 326WestJet
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Thu, 16 Oct - Fri, 31 Oct
Multiple Airlines Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
C$ 350Multiple Airlines
Find Deal
Thu, 30 Oct - Mon, 3 Nov
Multiple Airlines Logo
5:15 p.m. - 8:32 a.m.YYZ-MDW
16h 17m1 stop
Multiple Airlines Logo
9:32 a.m. - 2:05 p.m.MDW-YYZ
27h 33m1 stop
C$ 351Multiple Airlines
Find Deal
Sat, 18 Oct - Sat, 25 Oct
WestJet Logo
6:20 a.m. - 10:30 a.m.YYZ-MDW
5h 10m1 stop
WestJet Logo
10:35 a.m. - 4:50 p.m.MDW-YYZ
5h 15m1 stop
C$ 352WestJet
Find Deal
Tue, 21 Oct - Fri, 31 Oct
Multiple Airlines Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
Multiple Airlines Logo
9:32 a.m. - 8:00 p.m.MDW-YYZ
9h 28m1 stop
C$ 354Multiple Airlines
Find Deal
Mon, 13 Oct - Tue, 21 Oct
WestJet Logo
7:45 a.m. - 10:14 p.m.YYZ-MDW
15h 29m1 stop
WestJet Logo
1:48 p.m. - 11:18 p.m.MDW-YYZ
8h 30m1 stop
C$ 356WestJet
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Wed, 29 Oct - Wed, 5 Nov
WestJet Logo
6:00 p.m. - 9:45 a.m.YYZ-MDW
16h 45m1 stop
WestJet Logo
10:40 a.m. - 9:55 p.m.MDW-YYZ
10h 15m1 stop
C$ 359WestJet
Find Deal
Wed, 29 Oct - Wed, 5 Nov
WestJet Logo
6:00 p.m. - 9:45 a.m.YYZ-MDW
16h 45m1 stop
WestJet Logo
10:40 a.m. - 4:50 p.m.MDW-YYZ
5h 10m1 stop
C$ 361WestJet
Find Deal
Wed, 15 Oct - Tue, 21 Oct
WestJet Logo
6:00 p.m. - 10:14 p.m.YYZ-MDW
5h 14m1 stop
WestJet Logo
12:48 p.m. - 9:55 p.m.MDW-YYZ
8h 07m1 stop
C$ 362WestJet
Find Deal
Thu, 23 Oct - Sat, 1 Nov
Delta Logo
9:45 a.m. - 12:28 p.m.YYZ-MDW
3h 43m1 stop
Delta Logo
1:11 p.m. - 5:19 p.m.MDW-YYZ
3h 08m1 stop
C$ 419Delta
Find Deal

Everything you should know

Top airlines
WestJet
Cheapest • from C$ 326 (round-trip)
Porter Airlines
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
February
Cheapest • 31% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 326
Overall average: C$ 456
WestJet
Sat 18/10Sat 25/10
YYZ - MDW • 1 stop
Cheapest one-way flights
C$ 200
Multiple Airlines
Wed 29/10
YYZ - MDW • 1 stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
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.

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$ 303 (return) on average. On the other hand, the most expensive months are September and August, where the average cost of round-trip tickets is C$ 781 and C$ 548 respectively.

Good to know

Low seasonFebruary
Cheapest flightC$ 200
Best time to beat the crowds (31% less expensive on average)
Most popular time to fly and prices are also 8% lower 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$ 145 for a one-way ticket and C$ 236 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.

  • Which is the best airline for flights from Toronto to Chicago, Porter Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are Porter Airlines and WestJet. With an average price for the route of C$ 349 and an overall rating of 7.9, Porter Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of C$ 677 and an overall rating of 7.2.

  • 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.
7.9
Porter AirlinesOverall score based on 363 reviews
7.0Entertainment
8.6Crew
8.1Boarding
7.6Food
7.9Comfort
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

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.

I like how spacious the plane was but I did not like the fact that there was no entertainment

No dogs! Can we have no dogs in the cabin? Why was there a yappy little dog behind me? Lucky I had ear plugs. Sorry for others without

In spite of purchasing premium, I felt it was perhaps the most uncomfortable seat I have flown in. The base was either broken or poorly made and had no support. Even placing pillows and blankets on the seat (1D aisle) didn’t help. It made for a long and mostly sleepless six hour flight. Crew also were very loudly talking to each other through the night making it very hard to sleep. It was purchased for the price, so I get the risk, but was not impressed.

Good value, minor delay due to waiting for inbound plane but they gave accurate information about wait time. Able to switch to a seat by my husband thanks to a kind flight attendant

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.

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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