YTO - MDW

C$ 113 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 26/8. 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 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, 11 Sep - Thu, 18 Sep
Porter Airlines Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
Porter Airlines Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 161Porter Airlines
Find Deal
Mon, 1 Sep - Mon, 8 Sep
Porter Airlines Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Porter Airlines Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 164Porter Airlines
Find Deal
Fri, 5 Sep - Sun, 7 Sep
Air Transat Logo
7:30 a.m. - 8:19 a.m.YTZ-MDW
1h 49mdirect
Air Transat Logo
9:15 a.m. - 11:57 a.m.MDW-YTZ
1h 42mdirect
C$ 204Air Transat
Find Deal
Mon, 1 Sep - Wed, 3 Sep
Air Transat Logo
9:00 a.m. - 9:50 a.m.YTZ-MDW
1h 50mdirect
Air Transat Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 228Air Transat
Find Deal
Thu, 25 Sep - Mon, 29 Sep
 Logo
7:50 a.m. - 8:39 a.m.YTZ-MDW
1h 49mdirect
 Logo
5:20 p.m. - 8:02 p.m.MDW-YTZ
1h 42mdirect
C$ 270
Find Deal
Wed, 27 Aug - Wed, 3 Sep
 Logo
3:35 p.m. - 4:24 p.m.YTZ-MDW
1h 49mdirect
 Logo
9:35 a.m. - 12:17 p.m.MDW-YTZ
1h 42mdirect
C$ 275
Find Deal
Sat, 13 Sep - Sat, 20 Sep
Delta Logo
12:14 p.m. - 6:35 p.m.YYZ-MDW
7h 21m1 stop
Delta Logo
1:43 p.m. - 11:20 p.m.MDW-YYZ
8h 37m1 stop
C$ 292Delta
Find Deal
Sat, 30 Aug - Sat, 6 Sep
Delta Logo
6:30 a.m. - 12:28 p.m.YYZ-MDW
6h 58m1 stop
Delta Logo
6:17 p.m. - 10:58 p.m.MDW-YYZ
3h 41m1 stop
C$ 293Delta
Find Deal
Sat, 30 Aug - Sat, 6 Sep
WestJet Logo
8:00 p.m. - 9:12 p.m.YYZ-MDW
26h 12m2 stops
WestJet Logo
7:17 p.m. - 11:53 a.m.MDW-YYZ
15h 36m1 stop
C$ 384WestJet
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$ 385WestJet
Find Deal
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?

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

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Toronto to Chicago Midway Airport.

Our data shows that the cheapest route for a return flight from Toronto to Chicago Midway Airport cost C$ 183 and was between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is C$ 183.

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 May, where tickets cost C$ 283 (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$ 443 and C$ 381 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$ 387, prices are generally cheapest when you fly direct.


Good to know

Low seasonJanuary
Cheapest flightC$ 113
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly (7% more expensive 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$ 82 for a one-way ticket and C$ 117 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, WestJet, WestJet Encore, and Delta.

  • 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$ 331 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$ 373 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$ 128 or less one-way and C$ 199 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 318 reviews
8.7Crew
8.2Boarding
8.0Comfort
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.

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The plane was pretty full, and we dis not have any includes meal for our 4h30 flight? And on-board entertainment wasn't available, there was no TV or plugging to charger your device on the plane. They told us to download an app if we wanted to watch movies but it never connected, that was a disappointment, the r we st was very good though and the crew were really nice!

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

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

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