MDW - YTO

$85 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 1/29. 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 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$191
Overall average: $367
Porter Airlines
Thu 1/29Sun 2/1
MDW - YTZ • Non-stop
Cheapest one-way
$85
Porter Airlines
Thu 1/29
MDW - YTZ • Non-stop
Our travelers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
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 $191 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
MDW-YTZ
Cheapest
MDW-YTZ
Most popular
Insights
Insights
Insights
Insights
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Toronto!
Flight Deals
Booking Insights
Expert advice
Flight 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

Thu, Jan 29 - Sun, Feb 1
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
$191Porter Airlines
Tue, Jan 20 - Tue, Jan 27
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
$194Porter Airlines
Tue, Jan 20 - Tue, Jan 27
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
9:20 am - 10:10 am
YTZ
-
MDW
1h 50mnonstop
$197Porter Airlines
Fri, Jan 30 - Sat, Jan 31
Porter Airlines Logo
11:05 am - 1:47 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
11:00 am - 11:50 am
YTZ
-
MDW
1h 50mnonstop
$199Porter Airlines
Thu, Feb 5 - Mon, Feb 9
Delta Logo
9:33 am - 4:12 pm
MDW
-
YYZ
5h 39m1 stop
Delta Logo
7:45 am - 12:46 pm
YYZ
-
MDW
6h 01m1 stop
$234Delta
Thu, Jan 29 - Tue, Feb 3
Delta Logo
1:26 pm - 7:08 pm
MDW
-
YYZ
4h 42m1 stop
Delta Logo
12:12 pm - 5:55 pm
YYZ
-
MDW
6h 43m1 stop
$251Delta
Mon, Jan 12 - Mon, Jan 19
Multiple Airlines Logo
4:31 pm - 2:05 pm
MDW
-
YYZ
20h 34m1 stop
Multiple Airlines Logo
6:05 am - 8:52 am
YYZ
-
MDW
3h 47m1 stop
$299Multiple Airlines
Wed, Jan 7 - Fri, Jan 9
WestJet Logo
6:14 pm - 9:04 am
MDW
-
YYZ
13h 50m1 stop
WestJet Logo
10:05 am - 12:48 pm
YYZ
-
MDW
3h 43m1 stop
$302WestJet
Wed, Jan 7 - Tue, Jan 13
WestJet Logo
6:14 pm - 10:41 pm
MDW
-
YYZ
3h 27m1 stop
WestJet Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
$303WestJet
Thu, Jan 29 - Tue, Feb 3
Multiple Airlines Logo
5:01 pm - 11:46 am
MDW
-
YYZ
17h 45m2 stops
Multiple Airlines Logo
11:30 am - 5:29 pm
YYZ
-
MDW
6h 59m1 stop
$314Multiple Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Chicago Midway Airport to Toronto costs $168 on the route between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ). It is also the most popular route.

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.

No, with an average price for the route of $287, prices are generally cheapest when you fly direct.

Expert advice

Expert advice for your flight from Midway to Toronto

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
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.

YTZ

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

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

Good to know

Low seasonJuly
Cheapest flight$85
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

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 $85 for a one-way ticket and $191 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?

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

  • 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 $126 or less one-way and $243 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 399 reviews
7.6Food
7.0Entertainment
8.6Crew
7.9Comfort
8.2Boarding
Airline reviews

Much roomer than air Canada! Great flight for the price. No complaints

8.0 ExcellentDiane, Dec 2025
TPA - YYZ
Read more Porter Airlines reviews

Much roomer than air Canada! Great flight for the price. No complaints

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

As a first time flyer with Porter I was happy with the service and comfort of the airline.

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Other than wifi no on board entertainment. Will use them again, roomier seats than other airlines and snacks and beverages, better than average

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

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.👍

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

Information on your arrival and departure airports