YTO - MDW

C$ 185 Find Cheap Flights from Toronto 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 Toronto to Midway departing on 28/11. 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, 0 bags

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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Flight Deals

Cheap Flights from Toronto to Midway (YTO-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Toronto 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 Toronto to Midway

Thu, 13 Nov - Mon, 17 Nov
Porter Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 262Porter Airlines
Find Deal
Tue, 11 Nov - Fri, 14 Nov
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 267Porter Airlines
Find Deal
Thu, 11 Dec - Sun, 14 Dec
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 271Porter Airlines
Find Deal
Tue, 11 Nov - Fri, 14 Nov
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 281Air Transat
Find Deal
Tue, 18 Nov - Thu, 20 Nov
Air Transat Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
4:15 p.m. - 6:57 p.m.MDW-YTZ
1h 42mdirect
C$ 290Air Transat
Find Deal
Thu, 20 Nov - Sat, 22 Nov
Delta Logo
3:38 p.m. - 6:08 p.m.YYZ-MDW
3h 30m1 stop
Delta Logo
6:48 p.m. - 11:05 p.m.MDW-YYZ
3h 17m1 stop
C$ 295Delta
Find Deal
Thu, 4 Dec - Sun, 7 Dec
Delta Logo
12:13 p.m. - 6:00 p.m.YYZ-MDW
6h 47m1 stop
Delta Logo
9:34 a.m. - 2:48 p.m.MDW-YYZ
4h 14m1 stop
C$ 297Delta
Find Deal
Sat, 15 Nov - Mon, 24 Nov
KLM Logo
6:05 a.m. - 8:52 a.m.YYZ-MDW
3h 47m1 stop
KLM Logo
6:48 p.m. - 11:05 p.m.MDW-YYZ
3h 17m1 stop
C$ 308KLM
Find Deal
Fri, 21 Nov - Sun, 23 Nov
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 311Multiple Airlines
Find Deal
Tue, 11 Nov - Thu, 13 Nov
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.YTZ-MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.MDW-YTZ
1h 42mdirect
C$ 319Multiple Airlines
Find Deal

Everything you should know

Top airlines
Porter Airlines
Cheapest • from C$ 262 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
YTZ-MDW
Cheapest
YTZ-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 29% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 262
Overall average: C$ 544
Porter Airlines
Thu 13/11Mon 17/11
YTZ - MDW • Direct
Cheapest one-way flights
C$ 185
Typical prices: C$ 187-C$ 245
Porter Airlines
Fri 28/11
YTZ - MDW • Direct
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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 Toronto to Midway flights

Get data-powered insights and trends into flights from Toronto 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 to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Toronto to Chicago Midway Airport departing in November.

What is the cheapest Toronto to Chicago Midway Airport flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Toronto to Chicago Midway Airport costs C$ 296 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). It is also the most popular route.

What is the cheapest month to fly from Toronto 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 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 to Chicago Midway Airport is September, where tickets cost C$ 241 (return) on average. On the other hand, the most expensive months are January and December, where the average cost of round-trip tickets is C$ 429 and C$ 387 respectively.

Can I save money by flying with a layover from Toronto to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at C$ 360 on average.

Good to know

Low seasonJanuary
Cheapest flightC$ 185
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto to Midway

Are your dates flexible? Find out the best times to travel from Toronto 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 to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from Toronto to Chicago Midway Airport was C$ 185 for a one-way ticket and C$ 262 for a round-trip.

  • Which airports will I be using when flying from Toronto to Chicago Midway Airport?

    Toronto is served by 2 major airports and there is only 1 main airport in Chicago Midway Airport. You will leave Toronto from one of these airports: Toronto Island or Toronto Pearson Intl. You will be arriving at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Chicago Midway Airport?

    Air Canada, United Airlines, American Airlines, and WestJet Encore offer inflight Wi-Fi service on the Toronto to Chicago Midway Airport flight route.

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

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto to Chicago Midway Airport flight route.

  • On which days can I fly direct from Toronto to Chicago Midway Airport?

    There are direct flights from Toronto to Chicago Midway Airport on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are Porter Airlines and Air Transat. With an average price for the route of C$ 316 and an overall rating of 8.0, Porter Airlines is the most popular choice. Air Transat is also a great choice for the route, with an average price of C$ 381 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Toronto 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 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 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 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Toronto to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 197 or less one-way and C$ 348 or less round-trip.

Prefer to fly direct from Toronto to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto to Chicago Midway.
Find which airlines fly direct from Toronto to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Toronto to Chicago Midway

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more nonstop flights

Direct returns

Chicago Midway to Toronto

Monday

Porter Airlines

Porter Airlines

Tuesday

Porter Airlines

Porter Airlines

Wednesday

Porter Airlines

Porter Airlines

Thursday

Porter Airlines

Porter Airlines

Friday

Porter Airlines

Porter Airlines

Saturday

Porter Airlines

Porter Airlines

Sunday

Porter Airlines

Porter Airlines

See more nonstop flights

Reviews of the top airlines flying from Toronto 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 Toronto 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 384 reviews
7.0Entertainment
8.6Crew
8.0Comfort
8.2Boarding
7.6Food
Airline reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

8.0 ExcellentPilar, Oct 2025FLL - YOW
Read more Porter Airlines reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

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

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.

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Everything was horrible. On the day of my departure, I was denied check-in and boarding because my reservation only showed one of my last names, while my passport contains both. This minor discrepancy could have been easily corrected, but I was informed that no adjustment could be made. As a result, I lost not only my outbound flight but also my return flight and had to purchase a new ticket at a significantly higher cost.

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

Everything you need to know for your flight from Toronto to Midway

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