$94 Find Cheap Flights from Chicago Midway Airport to Canada

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 Canada departing on 6/12. 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

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Cheap Flights from Midway to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$216
Calgary
Calgary1 stop$290
Halifax
Halifax2 stops$375
Ottawa
Ottawa1 stop$353
Winnipeg
Winnipeg1 stop$413
Québec City
Québec City2 stops$471
St. John's
St. John's1 stop$504
Saskatoon
Saskatoon1 stop$416
Thunder Bay
Thunder Bay1 stop$513
Toronto
Torontononstop$216
Calgary
Calgary1 stop$290
Halifax
Halifax2 stops$375
Ottawa
Ottawa1 stop$353
Winnipeg
Winnipeg1 stop$413
Québec City
Québec City2 stops$471
St. John's
St. John's1 stop$504
Saskatoon
Saskatoon1 stop$416
Thunder Bay
Thunder Bay1 stop$513

Book Cheap Midway to Canada Plane Tickets

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

Fri, Apr 24 - Mon, Apr 27
Porter Airlines Logo
4:05 pm - 10:45 pm
MDW
-
YUL
5h 40m
1 stop
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
$208Porter Airlines
Fri, Jun 5 - Mon, Jun 8
Porter Airlines Logo
10:25 am - 5:15 pm
MDW
-
YUL
5h 50m
1 stop
Porter Airlines Logo
6:30 am - 9:40 am
YUL
-
MDW
4h 10m
1 stop
$209Porter Airlines
Thu, Apr 23 - Fri, May 1
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
$216Porter Airlines
Sat, Apr 11 - Sun, Apr 12
Porter Airlines Logo
12:55 pm - 3:37 pm
MDW
-
YTZ
1h 42mnonstop
Porter Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
$216Porter Airlines
Thu, Apr 23 - Fri, May 1
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
$217Porter Airlines
Sat, May 30 - Tue, Jun 2
Delta Logo
6:36 pm - 10:59 pm
MDW
-
YYZ
3h 23m
1 stop
Delta Logo
12:29 pm - 5:56 pm
YYZ
-
MDW
6h 27m
1 stop
$247Delta
Fri, Jun 5 - Wed, Jun 10
Delta Logo
9:23 am - 6:31 pm
MDW
-
YYZ
8h 08m
1 stop
Delta Logo
12:09 pm - 6:31 pm
YYZ
-
MDW
7h 22m
1 stop
$269Delta
Tue, Apr 14 - Sun, May 3
Multiple Airlines Logo
7:30 am - 7:35 pm
MDW
-
YYZ
11h 05m
1 stop
Multiple Airlines Logo
5:50 pm - 1:00 pm
YYZ
-
MDW
20h 10m
1 stop
$328Multiple Airlines
Tue, Apr 14 - Wed, May 6
Multiple Airlines Logo
7:30 am - 8:10 pm
MDW
-
YYZ
11h 40m
2 stops
Multiple Airlines Logo
11:30 am - 4:26 pm
YYZ
-
MDW
5h 56m
1 stop
$338Multiple Airlines
Sat, May 30 - Sun, May 31
WestJet Logo
1:59 pm - 8:39 pm
MDW
-
YVR
8h 40m
1 stop
WestJet Logo
1:15 pm - 8:43 am
YVR
-
MDW
17h 28m
2 stops
$506WestJet
Booking Insights

KAYAK's insights & trends for Midway to Canada flights

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

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

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

The cheapest ticket to Canada from Chicago Midway Airport found in the last 72 hours was to Toronto, at $176 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Toronto Island Airport (YTZ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $176.

What is the cheapest time of day to fly to Canada?

The average price for all round-trip flights from Chicago Midway Airport to Canada depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Canada is generally in the morning, when round-trip flights cost $257 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Canada is generally in the evening, which is peak travel time and where the average cost of a ticket is $258.

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

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 $260, prices are generally cheapest when you fly direct.

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

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 Canada, 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 Canada is July, when tickets cost $179 (return) on average. On the other hand, the most expensive months are June and November, when the average cost of round-trip tickets is $442 and $287 respectively.

Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Chicago Midway Airport to Toronto Island

FAQs - booking Canada flights

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

    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 Canada.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago Midway Airport to Canada?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago Midway Airport to Canada 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 Canada?

    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 from Chicago Midway Airport to Canada with an airline and back 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 Canada?

    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 from Chicago Midway Airport to Canada up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Midway to Canada

 
Need help choosing which airline to fly with from Midway to Canada? 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 428 reviews
8.0Comfort
8.2Boarding
7.0Entertainment
8.6Crew
7.6Food
Airline reviews

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

2.0 MediocreAnonymous, Mar 2026
NAS - YOW
Read more Porter Airlines reviews

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

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.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

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

Information on your arrival and departure airports