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Find cheap flights from Toronto Pearson Airport to Chicago Midway Airport from C$ 217

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 21/5. 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
0 bags
Thu 6/6
Thu 13/6

Search 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
In the last 7 days, travellers have searched 42,573,820 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
12:30 p.m. - 5:06 p.m.YYZ-MDW
5h 36m1 stop
9:29 a.m. - 5:08 p.m.MDW-YYZ
6h 39m1 stop
C$ 372Delta
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Fri, 24 May - Mon, 1 Jul
6:04 a.m. - 8:48 a.m.YYZ-MDW
3h 44m1 stop
5:45 p.m. - 10:50 p.m.MDW-YYZ
4h 05m1 stop
C$ 392Delta
Find Deal
Fri, 7 Jun - Sun, 9 Jun
6:04 a.m. - 8:48 a.m.YYZ-MDW
3h 44m1 stop
9:28 a.m. - 5:08 p.m.MDW-YYZ
6h 40m1 stop
C$ 407Delta
Find Deal
Fri, 7 Jun - Sat, 8 Jun
6:04 a.m. - 8:51 a.m.YYZ-MDW
3h 47m1 stop
9:28 a.m. - 5:08 p.m.MDW-YYZ
6h 40m1 stop
C$ 417Delta
Find Deal
Sat, 1 Jun - Sat, 8 Jun
7:45 a.m. - 1:06 p.m.YYZ-MDW
6h 21m1 stop
2:05 p.m. - 11:50 p.m.MDW-YYZ
8h 45m1 stop
C$ 422WestJet
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Sun, 1 Sep - Thu, 5 Sep
9:45 a.m. - 5:06 p.m.YYZ-MDW
8h 21m1 stop
5:45 p.m. - 10:50 p.m.MDW-YYZ
4h 05m1 stop
C$ 424Delta
Find Deal
Mon, 20 May - Sat, 27 Jul
7:45 a.m. - 10:01 p.m.YYZ-MDW
15h 16m1 stop
6:00 a.m. - 9:57 p.m.MDW-YYZ
14h 57m1 stop
C$ 431WestJet
Find Deal
Sat, 1 Jun - Mon, 3 Jun
1:25 p.m. - 10:01 p.m.YYZ-MDW
9h 36m1 stop
2:15 p.m. - 11:14 p.m.MDW-YYZ
7h 59m1 stop
C$ 454WestJet
Find Deal
Sat, 1 Jun - Tue, 4 Jun
7:10 p.m. - 4:55 p.m.YYZ-MDW
22h 45m1 stop
12:42 p.m. - 12:10 p.m.MDW-YYZ
22h 28m1 stop
C$ 459WestJet
Find Deal
Fri, 31 May - Tue, 4 Jun
8:30 p.m. - 5:50 a.m.YYZ-MDW
10h 20m1 stop
9:08 p.m. - 5:56 p.m.MDW-YYZ
19h 48m2 stops
C$ 820
Find Deal
Fri, 17 May - Sat, 18 May

Flights from Pearson Intl to Midway - Travel Insights & Trends

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 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 March, where tickets cost C$ 295 on average. On the other hand, the most expensive months are June and August, where the average cost of tickets is C$ 520 and C$ 468 respectively.

How far in advance should I book a flight from Toronto Pearson Intl Airport to Chicago Midway Airport?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Toronto Pearson Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Toronto Pearson Intl Airport to Chicago Midway Airport, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 16 days before departure.

Which airlines provide the cheapest flights from Toronto Pearson Airport to Chicago Midway Airport?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the last 72 hours, the best return deals on flights connecting Toronto Pearson Airport to Chicago Midway Airport were found on Delta (C$ 372) and WestJet (C$ 422). Delta proposed the cheapest one-way flight at C$ 220.

Good to know

Low season

January

High season

February

Cheapest flight

C$ 217
Best time to beat the crowds (37% less expensive on average)
Most popular time to fly and prices are also 39% 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$ 159 for a one-way ticket and C$ 272 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.

See more FAQs

Top 4 airlines serving 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.
8.8
Endeavor AirlinesOverall score based on 4 reviews
7.0Entertainment
9.5Crew
9.5Comfort
8.5Food
9.5Boarding
Airline reviews
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"
8.6 ExcellentIllan, Jun. 2019YYZ - JFK
Read more about Endeavor Airlines reviews
Pros: "seat space was great and I was lucky enough to have medium size passenger next to me :-)"
Cons: "Can't really think of anything . . . my expectations were exceeded"

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

Great! No food was available during the flight due to the catering service strike but snacks were given throughout the flight which was nice.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Crew was rude.didn’t even say hi or welcome to board

Nothing special. Unacceptable wait for baggage on arriving in Calgary

Departure delay on a late night flight. Made us even later. Tired but got home.

Westjet forced me to put my carry-on baggage in check-in probably because I was assigned seat 23A (the last row seat), which had no cabin space, which is unfair. I wanted to carry on my luggage so that I don't have to wait at the airport for my luggage. Also, because there was no cabin space, I was forced to keep my laptop bag under the seat, which I didn't want to as I was carrying 2 laptops and charger. The airline should basically tell people that if you are assigned a last row seat, then you are not allowed a cabin baggage or a personal item.

Easy processing, flight time was quick and staff was professional and kind.

It was delayed by two ours very full no room to move

They seem to have squeezed out a little more legroom in these planes! It was very nice to not have to fold in half to fit in the seats!

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Flight Ottawa to Toronto canceled and no crew was available to direct me on what to do. I opened a file and I wait to be compensated.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

The staff were so kind and helpful. We flew back from NY with another airline and it was horrible. We will always stick with Air Canada as everything was far better!

The boarding process in Toronto bad as they share space with domestic flights and when those domestic flights come in you are locked out behind closed doors until they are done and then its a mad rush to get your boarding gates and board. This is not so much due to Air Canada but with the GTAA, but Air Canada could use different gates especially early morning in order to prevent such travel angst.

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
21/5Tue
1 stop
10h 50mYYZ-MDW
C$ 217
14/5Tue
1 stop
16h 16mYYZ-MDW
C$ 219
12/6Wed
1 stopDelta
3h 44mYYZ-MDW
C$ 220
27/5Mon
1 stopDelta
7h 36mYYZ-MDW
C$ 223
14/5Tue
1 stop
16h 16mYYZ-MDW
C$ 231
5/6Wed
1 stopDelta
4h 02mYYZ-MDW
C$ 234
7/8Wed
1 stopWestJet
5h 39mYYZ-MDW
C$ 238
10/8Sat
1 stopWestJet
6h 49mYYZ-MDW
C$ 249
6/6Thu
1 stopWestJet
8h 01mYYZ-MDW
C$ 253
4/6Tue
1 stopWestJet
8h 01mYYZ-MDW
C$ 257

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Last minute flights from Pearson Intl to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
12/5Sun
multi-stopDelta
5h 36mYYZ-MDW
17/5Fri
multi-stopDelta
8h 25mMDW-YYZ
C$ 540
12/5Sun
multi-stopWestJet
9h 38mYYZ-MDW
26/5Sun
multi-stopWestJet
24h 04mMDW-YYZ
C$ 554
12/5Sun
multi-stopWestJet
4h 57mYYZ-MDW
13/5Mon
multi-stopWestJet
5h 12mMDW-YYZ
C$ 582
10/5Fri
multi-stopWestJet
6h 37mYYZ-MDW
18/5Sat
multi-stopWestJet
5h 14mMDW-YYZ
C$ 614
12/5Sun
multi-stopWestJet
5h 33mYYZ-MDW
18/5Sat
multi-stopWestJet
5h 14mMDW-YYZ
C$ 621
12/5Sun
multi-stopWestJet
4h 57mYYZ-MDW
18/5Sat
multi-stopWestJet
5h 14mMDW-YYZ
C$ 622
10/5Fri
multi-stopWestJet
5h 33mYYZ-MDW
13/5Mon
multi-stopWestJet
7h 12mMDW-YYZ
C$ 630
9/5Thu
multi-stopDelta
4h 02mYYZ-MDW
18/5Sat
multi-stopDelta
3h 59mMDW-YYZ
C$ 634
10/5Fri
multi-stopDelta
3h 55mYYZ-MDW
17/5Fri
multi-stopDelta
3h 59mMDW-YYZ
C$ 636
9/5Thu
multi-stop
24h 16mYYZ-MDW
11/5Sat
multi-stop
5h 14mMDW-YYZ
C$ 906

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Toronto Pearson Airport - Chicago Midway Airport Flights

Departure:

Toronto Pearson Airport (YYZ)Canada

Destination:

Chicago Midway Airport (MDW)United States

Return flight deals:

Chicago Midway Airport - Toronto Pearson Airport

Cabin classes: