MDW - YTO

$52 Find Cheap Flights from Chicago Midway Airport to Toronto

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 departing on 10/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Toronto

 
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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Flights Deals

Cheap Flights from Midway to Toronto (MDW-YTO)

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

Sun, Sep 14 - Wed, Sep 17
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$124Porter Airlines
Find Deal
Tue, Aug 26 - Tue, Sep 2
Porter Airlines Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$139Porter Airlines
Find Deal
Mon, Sep 22 - Wed, Sep 24
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$146
Find Deal
Thu, Aug 28 - Mon, Sep 1
Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Logo
9:00 am - 9:50 amYTZ-MDW
1h 50mnonstop
$150
Find Deal
Wed, Sep 10 - Fri, Sep 12
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
$184Air Transat
Find Deal
Sat, Aug 23 - Tue, Aug 26
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
$219Air Transat
Find Deal
Wed, Sep 10 - Fri, Sep 12
Delta Logo
9:30 am - 5:23 pmMDW-YYZ
6h 53m1 stop
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
$234Delta
Find Deal
Wed, Aug 20 - Fri, Sep 12
Delta Logo
9:31 am - 5:23 pmMDW-YYZ
6h 52m1 stop
Delta Logo
4:12 pm - 6:35 pmYYZ-MDW
3h 23m1 stop
$243Delta
Find Deal
Thu, Aug 21 - Sun, Aug 24
WestJet Logo
12:43 pm - 9:58 pmMDW-YYZ
8h 15m1 stop
WestJet Logo
6:07 pm - 9:36 amYYZ-MDW
16h 29m1 stop
$319WestJet
Find Deal
Thu, Aug 21 - Sun, Aug 24
WestJet Logo
12:43 pm - 9:58 pmMDW-YYZ
8h 15m1 stop
WestJet Logo
1:20 pm - 9:44 pmYYZ-MDW
9h 24m1 stop
$321WestJet
Find Deal
Expert advice

Expert advice for your flight from Midway to Toronto

 
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 flights

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

What is the cheapest Chicago Midway Airport to Toronto flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago Midway Airport to Toronto.

Our data shows that the cheapest route for a return flight from Chicago Midway Airport to Toronto cost $148 and was between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $148.

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

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, 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 is July, where tickets cost $187 (return) on average. On the other hand, the most expensive months are March and June, where the average cost of round-trip tickets is $381 and $371 respectively.

Can I save money by flying with a layover from Chicago Midway Airport to Toronto?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $257 on average.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$52
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 25% increase in price.
Flight from Chicago Midway Airport to Toronto Island

When to book flights from Midway to Toronto

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

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Toronto was $52 for a one-way ticket and $124 for a round-trip.

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

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

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

    All the following airlines offer inflight Wi-Fi service on the Chicago Midway Airport to Toronto flight route: American Airlines, Air Canada, United Airlines, Iberia, British Airways, and Finnair.

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

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

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

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

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

    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.

  • 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?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Toronto 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?

    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 with an airline and back to Chicago Midway Airport with another airline.

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

    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 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

  • Looking for a cheap flight? 25% of our users found flights on this route for $69 or less one-way and $168 or less round-trip.

Prefer to fly direct from Chicago Midway Airport to Toronto?

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

Direct departures

Chicago Midway to Toronto

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 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

 
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? 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 318 reviews
7.6Food
8.2Boarding
8.0Comfort
8.7Crew
7.0Entertainment
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

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.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

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. :)

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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