MDW - YTZ

$107 Find Cheap Flights from Chicago Midway Airport to Toronto Island

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Toronto Island departing on 11/23. 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 Toronto Island Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Toronto, 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 Chicago to Toronto, as well as popular online travel agencies
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Flight Deals

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

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

Tue, Nov 11 - Tue, Nov 18
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$225Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$226Porter Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$227Porter Airlines
Find Deal
Sun, Feb 22 - Tue, Feb 24
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$234Porter Airlines
Find Deal
Sun, Nov 23 - Sun, Nov 30
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$236Porter Airlines
Find Deal
Sun, Nov 9 - Thu, Nov 13
Porter Airlines Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$238Porter Airlines
Find Deal
Thu, Nov 13 - Thu, Nov 20
Multiple Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
9:15 am - 10:05 amYTZ-MDW
1h 50mnonstop
$262Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Air Transat Logo
11:00 am - 1:42 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$275Air Transat
Find Deal
Thu, Nov 6 - Sun, Nov 9
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$283Air Transat
Find Deal
Thu, Nov 6 - Sun, Nov 9
Air Transat Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
$284Air Transat
Find Deal

Everything you should know

Our travelers' advice
AI-generated summary based on content written by travel experts
Midway's compact terminal is easy to navigate.
Take the free shuttle from YTZ to Union Station.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Porter Airlines
Cheapest • from $225 (round-trip)
Porter Airlines
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
July
Cheapest • 38% price drop
June
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$225
Overall average: $294
Porter Airlines
Tue 11/11Tue 11/18
MDW - YTZ • Non-stop
Cheapest one-way
$107
Overall average: $143
Porter Airlines
Sun 11/23
MDW - YTZ • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toronto Island!
Expert advice

Expert advice for your flight from Midway to Toronto Island

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
MDW

Midway's compact terminal makes it easy to navigate, with all concourses accessible from the central check-in and security area.

Read more about MDWby Stefanie Waldek
YTZ

Take the free shuttle from YTZ to Union Station, connecting to public and regional transit every 15 minutes.

Read more about YTZby Jennifer Bain
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Jennifer Bain

Jennifer Bain

Expert on YTZ

Jennifer Bain

Jennifer Bain

Jennifer Bain is a Canadian travel writer who takes at least 50 flights a year and has proudly visited all 13 of Canada's provinces and territories. She is a former newspaper travel editor who has written three travel books. Jennifer is the Canada editor for U.S.-based National Parks Traveler and freelances for numerous other outlets.

Read more
Booking Insights

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

Get data-powered insights and trends into flights from Midway to Toronto Island to help you find the cheapest flights, the best time to fly and much more.

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

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

Your flight ticket price will generally be cheaper if you fly to Toronto Island on a Saturday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Saturday, and avoid Thursdays for better deals.

What is the cheapest month to fly from Chicago Midway Airport to Toronto Island Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Toronto Island 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 Chicago Midway Airport to Toronto Island Airport is July, where tickets cost $174 (return) on average. On the other hand, the most expensive months are March and January, where the average cost of round-trip tickets is $473 and $367 respectively.

Good to know

Low seasonMarch
Cheapest flight$107
Best time to beat the crowds but there is an average 68% increase in price.
Most popular time to fly and prices are also 32% lower on average.
Flight from Chicago Midway Airport to Toronto Island

When to book flights from Midway to Toronto Island

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Toronto Island Airport was $107 for a one-way ticket and $225 for a round-trip.

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

    Yes, you’ll need a passport to travel to Toronto Island from Chicago Midway Airport.

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

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

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

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

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

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

  • How does KAYAK find such low prices on flights from Chicago Midway Airport to Toronto Island?

    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 Chicago Midway Airport to Toronto Island.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Toronto Island?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto Island from Chicago Midway Airport 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 Chicago Midway Airport to Toronto Island?

    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 Toronto Island with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YTZ 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 Chicago Midway Airport to Toronto Island?

    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 Toronto Island from Chicago Midway Airport 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 Chicago Midway Airport to Toronto Island Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $84 or less one-way and $197 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Toronto Island?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Midway to Toronto Island

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Toronto. 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 Midway to Toronto Island? 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 370 reviews
7.0Entertainment
7.6Food
8.0Comfort
8.2Boarding
8.6Crew
Airline reviews

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

4.0 OkayAnonymous, Sep 2025LGA - YYZ
Read more Porter Airlines reviews

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

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.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

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.

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

Information on your arrival and departure airports

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