MDW - YTO

$106 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 7/15. 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
$228
Typical prices: $258-$348
Porter Airlines
Thu 7/16Sun 7/19
MDW - YTZ • Non-stop
Cheapest one-way
$106
Typical prices: $106-$128
Porter Airlines
Wed 7/15
MDW - YTZ • Non-stop
Top airlines
Porter Airlines
Cheapest • from $228 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Porter Airlines. Average duration is 1h 40m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top routes
MDW
-
YTZ
Cheapest
MDW
-
YTZ
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Porter Airlines
Most punctual • 86% on-time
Evening flights
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 53% price drop
May
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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
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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, Jul 16 - Sun, Jul 19
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$228Porter Airlines
Wed, Jul 22 - Wed, Jul 29
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$229Porter Airlines
Sun, Jul 12 - Thu, Jul 16
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$230Porter Airlines
Fri, Jul 17 - Sun, Jul 19
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$231Porter Airlines
Thu, Jul 16 - Mon, Jul 20
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$232Porter Airlines
Sat, Jul 18 - Sun, Jul 19
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
8:50 am - 9:40 am
YTZ
-
MDW
1h 50mnonstop
$233Porter Airlines
Fri, Sep 4 - Mon, Sep 7
Delta Logo
1:25 pm - 11:03 pm
MDW
-
YYZ
8h 38m
1 stop
Delta Logo
12:09 pm - 6:33 pm
YYZ
-
MDW
7h 24m
1 stop
$272Delta
Thu, Jul 9 - Sat, Jul 11
Delta Logo
9:19 am - 1:34 pm
MDW
-
YYZ
3h 15m
1 stop
Delta Logo
6:10 am - 12:38 pm
YYZ
-
MDW
7h 28m
1 stop
$289Delta
Fri, Sep 11 - Tue, Sep 15
Delta Logo
9:29 am - 5:20 pm
MDW
-
YYZ
6h 51m
1 stop
Delta Logo
6:00 am - 9:07 am
YYZ
-
MDW
4h 07m
1 stop
$298Delta
Fri, Jul 10 - Sun, Jul 12
KLM Logo
9:19 am - 3:20 pm
MDW
-
YYZ
5h 01m
1 stop
KLM Logo
6:10 am - 12:38 pm
YYZ
-
MDW
7h 28m
1 stop
$316KLM
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.

How much is a round-trip flight from Chicago Midway Airport to Toronto?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago Midway Airport to Toronto departing in July.

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 $199 on the route between Chicago Midway Airport (MDW) and Toronto Island Airport (YTZ). It is also the most popular route.

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 March, where tickets cost $58 (return) on average. On the other hand, the most expensive months are October and January, where the average cost of round-trip tickets is $199 and $187 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.

No, with an average price for the route of $273, prices are generally cheapest when you fly direct.

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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.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on MDW

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 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 seasonJanuary
Cheapest flight$106
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 2% 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 5 days, the lowest price for a flight from Chicago Midway Airport to Toronto was $106 for a one-way ticket and $228 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, Porter Airlines, and United 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.

  • Which airline alliances offer flights from Chicago Midway Airport to Toronto?

    SkyTeam is the only airline alliance operating flights between Chicago Midway Airport and Toronto.

  • 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 $117 or less one-way and $240 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 441 reviews
8.0Comfort
8.2Boarding
8.6Crew
6.9Entertainment
7.5Food
Airline reviews

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

6.0 GoodHarsh, Apr 2026
JFK - YYZ
Read more Porter Airlines reviews

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

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

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

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

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.

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.

Flight was delayed over 2 hours, then landed at a different airport!

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.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)