YTO - MDW

C$ 165 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 12/5. 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
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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Everything you should know

Cheapest round-trip
C$ 260
Typical prices: C$ 256-C$ 306
Porter Airlines
Thu 5/3Fri 6/3
YTZ - MDW • Direct
Cheapest one-way flights
C$ 165
Typical prices: C$ 196-C$ 329
Air Transat
Tue 12/5
YTZ - MDW • Direct
Top airlines
Porter Airlines
Cheapest • from C$ 260 (round-trip)
Porter Airlines
Best reviews • 7.9 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 • 24% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
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, 5 Mar - Fri, 6 Mar
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$ 260Porter Airlines
Mon, 9 Mar - Mon, 16 Mar
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$ 262Porter Airlines
Thu, 19 Feb - Mon, 23 Feb
Multiple Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 269Multiple Airlines
Sun, 1 Mar - Sat, 7 Mar
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
12:45 p.m. - 3:27 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 270Multiple Airlines
Fri, 13 Feb - Sun, 15 Feb
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 272Porter Airlines
Mon, 20 Apr - Thu, 23 Apr
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$ 283Air Transat
Tue, 17 Feb - Sun, 22 Feb
Delta Logo
10:05 a.m. - 12:46 p.m.
YYZ
-
MDW
3h 41m
1 stop
Delta Logo
1:28 p.m. - 10:40 p.m.
MDW
-
YYZ
8h 12m
1 stop
C$ 304Delta
Thu, 19 Feb - Mon, 23 Feb
Delta Logo
12:11 p.m. - 5:37 p.m.
YYZ
-
MDW
6h 26m
1 stop
Delta Logo
6:17 p.m. - 10:40 p.m.
MDW
-
YYZ
3h 23m
1 stop
C$ 307Delta
Wed, 25 Feb - Wed, 4 Mar
WestJet Logo
6:15 a.m. - 8:54 a.m.
YYZ
-
MDW
3h 39m
1 stop
WestJet Logo
6:20 p.m. - 10:40 p.m.
MDW
-
YYZ
3h 20m
1 stop
C$ 319WestJet
Thu, 19 Feb - Mon, 23 Feb
WestJet Logo
6:15 a.m. - 8:54 a.m.
YYZ
-
MDW
3h 39m
1 stop
WestJet Logo
1:28 p.m. - 7:09 p.m.
MDW
-
YYZ
4h 41m
1 stop
C$ 322WestJet
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 March.

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$ 231 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$ 233 (return) on average. On the other hand, the most expensive months are December and July, where the average cost of round-trip tickets is C$ 369 and C$ 364 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.

No, with an average price for the route of C$ 317, prices are generally cheapest when you fly direct.

Good to know

Low seasonDecember
Cheapest flightC$ 165
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly and prices are also 4% 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$ 165 for a one-way ticket and C$ 260 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?

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

  • 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$ 273 and an overall rating of 7.9, Porter Airlines is the most popular choice. Air Transat is also a great choice for the route, with an average price of C$ 348 and an overall rating of 7.7.

  • 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$ 185 or less one-way and C$ 260 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.
7.9
Porter AirlinesOverall score based on 412 reviews
8.6Crew
7.5Food
6.9Entertainment
8.2Boarding
7.9Comfort
Airline reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

6.0 GoodBeat, Jan 2026
YUL - YVR
Read more Porter Airlines reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average

Organization and the adjusted times but the snacks could be of a bigger portion

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 did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

Very good. A lot better experience then I expected for an economy flight.

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.

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

Information on your arrival and departure airports