YTZ - MDW

$124 Find Cheap Flights from Toronto Island 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 Island to Midway departing on 7/22. 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
$204
Typical prices: $332-$233
Porter Airlines
Tue 5/5Fri 5/8
YTZ - MDW • Non-stop
Cheapest one-way
$125
Porter Airlines
Wed 7/22
YTZ - MDW • Non-stop
Nonstop flights
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
Most punctual • 85% on-time
Best time • Fewest delays
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We hope you love your trip to Midway!
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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

Tue, May 5 - Fri, May 8
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$204Porter Airlines
Wed, May 13 - Wed, May 20
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$205Porter Airlines
Sat, May 9 - Sun, May 10
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$206Porter Airlines
Thu, May 7 - Sun, May 10
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$207Porter Airlines
Fri, May 22 - Sun, May 31
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$208Porter Airlines
Wed, Jun 24 - Fri, Jul 3
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$209Porter Airlines
Thu, May 7 - Mon, May 11
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$210Porter Airlines
Fri, May 22 - Mon, May 25
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$211Porter Airlines
Wed, Jul 8 - Sat, Jul 11
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
$212Porter Airlines
Thu, May 7 - Sun, May 10
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$213Porter Airlines
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 May.

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 Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Toronto Island, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

Good to know

Low seasonSeptember
Cheapest flight$125
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly and prices are also 3% 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 3 days, the lowest price for a flight from Toronto Island Airport to Chicago Midway Airport was $124 for a one-way ticket and $204 for a round-trip.

  • Do I need a passport to fly between Toronto Island and Chicago Midway Airport?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Toronto Island and on arrival in Chicago Midway Airport.

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

    Toronto Island and Chicago Midway Airport are both served by 1 main airport. You will leave Toronto Island from Toronto Island and will be arriving at Chicago Midway.

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

    Air Canada, United Airlines, American Airlines, WestJet Encore, and Delta 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 nonstop 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 travelers 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. Booking your flights between Toronto Island and MDW can sometimes prove cheaper using this method.

  • 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 $178 or less one-way and $271 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 direct 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 direct 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 435 reviews
8.6Crew
8.2Boarding
7.0Entertainment
8.0Comfort
7.6Food
Airline reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

10.0 ExcellentAnonymous, Apr 2026
YHM - YHZ
Read more Porter Airlines reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

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.

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.

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

Information on your arrival and departure airports