MDW - YTZ

$61 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 8/26. 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
Expert advice
Booking Insights
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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Toronto Island

Wed, Sep 3 - Mon, Sep 8
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$158Porter Airlines
Find Deal
Wed, Sep 3 - Sat, Sep 6
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$191Porter Airlines
Find Deal
Wed, Sep 3 - Sun, Sep 7
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$192Porter Airlines
Find Deal
Wed, Sep 3 - Wed, Sep 3
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$193Porter Airlines
Find Deal
Wed, Sep 3 - Sun, Sep 7
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$194Porter Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$195Porter Airlines
Find Deal
Wed, Sep 10 - Thu, Sep 18
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$196Porter Airlines
Find Deal
Sat, Sep 27 - Sat, Oct 4
 Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
 Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Wed, Sep 10 - Thu, Sep 18
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
$247Air Transat
Find Deal
Fri, Sep 5 - Mon, Sep 8
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$249Air Transat
Find Deal
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 Wednesday, and avoid Thursdays for better deals.

Good to know

Low seasonJune
Cheapest flight$61
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 31% 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 $61 for a one-way ticket and $158 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 $86 or less one-way and $167 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

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Tuesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Wednesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Thursday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Friday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Saturday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Sunday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

See more direct flights

Direct returns

Toronto Island to Chicago Midway

Monday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Tuesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Wednesday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Thursday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Friday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Saturday

Air Transat, Porter Airlines

Air Transat, Porter Airlines

Sunday

Air Transat, Porter Airlines

Air Transat, 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.
8.0
Porter AirlinesOverall score based on 332 reviews
8.7Crew
8.0Comfort
7.0Entertainment
8.2Boarding
7.6Food
Airline reviews

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

2.0 MediocreKirsten, Aug 2025BOS - YOW
Read more Porter Airlines reviews

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.

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.

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

Information on your arrival and departure airports

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