YTZ - MDW

C$ 192 Find Cheap Flights from Toronto Island to Chicago Midway Airport – Compare and Save

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 Island 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, 0 bags

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Everything you should know

Cheapest round-trip
C$ 291
Typical prices: C$ 268-C$ 437
Porter Airlines
Mon 31/8Mon 21/9
YTZ - MDW • Direct
Cheapest one-way flights
C$ 192
Porter Airlines
Wed 26/8
YTZ - MDW • Direct
Direct flights
Every day
You can fly direct with Porter Airlines. Average duration is 1h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Avoid delays
Porter Airlines
Most punctual • 85% on-time
Morning flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
February
Cheapest • 100% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Toronto Island to Midway (YTZ-MDW)

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

Mon, 31 Aug - Mon, 21 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 291Porter Airlines
Tue, 25 Aug - Wed, 9 Sep
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 292Porter Airlines
Mon, 7 Sep - Thu, 10 Sep
Porter Airlines Logo
10:10 a.m. - 11:00 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 292Porter Airlines
Thu, 20 Aug - Sun, 23 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Wed, 19 Aug - Wed, 19 Aug
Porter Airlines Logo
8:55 a.m. - 9:45 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:15 p.m. - 5:55 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Fri, 28 Aug - Sun, 30 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:20 a.m. - 1:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Tue, 18 Aug - Thu, 20 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Fri, 21 Aug - Mon, 31 Aug
Porter Airlines Logo
1:45 p.m. - 2:35 p.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 298Porter Airlines
Thu, 10 Sep - Mon, 14 Sep
Air Transat Logo
10:10 a.m. - 11:00 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 308Air Transat
Tue, 15 Sep - Wed, 16 Sep
Air Transat Logo
10:10 a.m. - 11:00 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
11:45 a.m. - 2:25 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 308Air Transat
Booking Insights

KAYAK's insights & trends for Toronto Island to Midway flights

Get data-powered insights and trends into flights from Toronto Island 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 Island Airport 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 Island Airport to Chicago Midway Airport departing in August.

Flight prices are typical for this route right now.

Flights to Chicago Midway Airport from Toronto Island Airport usually cost between C$ 291 and C$ 583 in August.
The lowest price found in the past 5 days was C$ 291 on Porter Airlines (31 Aug–21 Sep).

What’s the cheapest day of the week to fly from Toronto Island to Chicago Midway Airport?

The average price of all round-trip flights from Toronto Island Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

When flying from Toronto Island to Chicago Midway Airport, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Wednesdays and the most expensive ones on Mondays.

What is the cheapest month to fly from Toronto Island 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 Island 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 Island Airport to Chicago Midway Airport is February, where tickets cost C$ 0 (return) on average. On the other hand, the most expensive months are June and November, where the average cost of round-trip tickets is C$ 605 and C$ 602 respectively.

Find deals

Good to know

Cheapest flight

C$ 192
Most popular time to fly and prices are also 8% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto Island to Midway

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

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

    In the last 5 days, the lowest price for a flight from Toronto Island Airport to Chicago Midway Airport was C$ 192 for a one-way ticket and C$ 291 for a round-trip.

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

    When flying out of Toronto Island you will be using Toronto Island. You will be landing at Chicago Midway Airport, also known as Chicago Midway.

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

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

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

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

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Toronto Island 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 Island 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 Island Airport to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 182 or less one-way and C$ 289 or less round-trip.

Prefer to fly direct from Toronto Island 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 Island to Chicago Midway.
Find which airlines fly direct from Toronto Island Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Toronto Island 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 Island

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 airline flying from Toronto Island 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 Island 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 449 reviews
8.0Comfort
8.6Crew
7.5Food
8.2Boarding
6.9Entertainment
Airline reviews

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.

6.0 GoodJen, Jan 2026
YTZ - BOS
Read more Porter Airlines reviews

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.

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

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.

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.

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

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.

Nothing to like about porter. Flight cancelled. No flight back to Boston for 2 days. No hotel accommodation. Terrible. Never again by porter.

Porter is the airline that does care. All trips with Porter have been smooth and relaxing. The extras are the customer appreciation. The others just don’t do that.

The flight was delayed for more than 2 hrs. The plane was changed and staff couldn’t count people so we had to wait even longer while waiting for take off.

Communication at the gate was adequate. Boarding was orderly. Seats are decent, with a reasonable amount of leg room. Flight was only 1.5 hours, so only a modest snack service (short bread cookie or small bag of chips) and a drink (coffee, tea, soda, cup of beer or wine). Exiting the plane was also orderly. Overall the flight was fine and the price reasonable.

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

Information on your arrival and departure airports

Toronto Island (YTZ)
Midway (MDW)