MDW - YTZ

$76 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 7/26. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Expert advice
Useful Info
Flights Deals

Cheap Flight Deals 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.

Recent round-trip flight deals from Midway to Toronto Island

KAYAK's recommended round-trip deals from the most popular airlines that fly from Midway to Toronto Island.
Discover the best prices for you by selecting your travel dates on KAYAK.
Porter Airlines Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$166Porter Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Porter Airlines Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:30 am - 8:19 amYTZ-MDW
1h 49mnonstop
$177Porter Airlines
Find Deal
Fri, Sep 26 - Tue, Sep 30
Porter Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$178Porter Airlines
Find Deal
Fri, Jun 20 - Tue, Jun 24
Porter Airlines Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$180Porter Airlines
Find Deal
Sat, May 24 - Mon, May 26
 Logo
9:40 am - 12:22 pmMDW-YTZ
1h 42mnonstop
 Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Sat, Jun 14 - Sat, Jun 21
 Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
 Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Thu, Jun 12 - Thu, Jun 19
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$236Air Transat
Find Deal
Fri, Aug 1 - Tue, Aug 5
APG Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
APG Airlines Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$259APG Airlines
Find Deal
Fri, Jun 13 - Fri, Jun 20
APG Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
APG Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$263APG Airlines
Find Deal
Thu, Jun 5 - Thu, Jun 5
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$291Air Transat
Find Deal
Tue, Aug 12 - Thu, Aug 14
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 offers a compact terminal with easy navigation, making it ideal for quick departures. Enjoy local dining options like Billy Goat Tavern.

Read more about MDWby Stefanie Waldek
YTZ

At YTZ, take the pedestrian tunnel for a quick 6-minute walk to the mainland, or opt for the 90-second ferry ride.

Read more about YTZby James March
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
James March

James March

Expert on YTZ

James March

James March

For UK-based James March, nothing beats the thrill and chaos of arriving in a new city for the first time, and he tries to put that feeling into his writing and inspire others to travel too. From Birmingham to Blackpool and Leicester to Liverpool, James has reviewed hotels, written narratives and created guides for those who love to travel.

Read more
Useful Info

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 Thursday and more expensive on a Sunday. On your return trip to Chicago Midway Airport, you should consider flying back on a Monday, and avoid Tuesdays for better deals.

Can I save money by flying with a layover from Chicago Midway Airport to Toronto Island 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 $515, prices are generally cheapest when you fly direct.

Good to know

Low seasonFebruary
High seasonApril
Cheapest flight$76
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 1% 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 $76 for a one-way ticket and $166 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?

    Air Canada, American Airlines, United Airlines, and Delta 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 $116 or less one-way and $218 or less round-trip.

Prefer to fly direct from Chicago Midway Airport 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
See more direct flights

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 285 reviews
8.1Comfort
8.2Boarding
7.0Entertainment
8.8Crew
7.6Food
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

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.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.