$101 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 7/6. 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$218
Calgary
Calgary1 stop$352
Halifax
Halifax1 stop$394
Ottawa
Ottawa1 stop$414
Winnipeg
Winnipeg2 stops$397
Québec City
Québec City1 stop$535
St. John's
St. John's2 stops$568
Saskatoon
Saskatoon2 stops$522
Thunder Bay
Thunder Bay1 stop$485
Toronto
Torontononstop$218
Calgary
Calgary1 stop$352
Halifax
Halifax1 stop$394
Ottawa
Ottawa1 stop$414
Winnipeg
Winnipeg2 stops$397
Québec City
Québec City1 stop$535
St. John's
St. John's2 stops$568
Saskatoon
Saskatoon2 stops$522
Thunder Bay
Thunder Bay1 stop$485

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

Thu, Jun 25 - Mon, Jun 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
$218Porter Airlines
Fri, Jul 10 - Mon, Jul 13
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$219Porter Airlines
Tue, Jul 21 - Sat, Jul 25
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
$220Porter Airlines
Thu, Jul 2 - Sun, Jul 5
KLM Logo
1:26 pm - 11:02 pm
MDW
-
YYZ
8h 36m
1 stop
KLM Logo
6:05 am - 12:46 pm
YYZ
-
MDW
7h 41m
1 stop
$265KLM
Thu, Jul 2 - Mon, Jul 6
KLM Logo
1:26 pm - 11:02 pm
MDW
-
YYZ
8h 36m
1 stop
KLM Logo
6:05 am - 12:46 pm
YYZ
-
MDW
7h 41m
1 stop
$272KLM
Sun, Sep 20 - Tue, Sep 29
Delta Logo
9:30 am - 5:20 pm
MDW
-
YYZ
6h 50m
1 stop
Delta Logo
6:00 am - 12:34 pm
YYZ
-
MDW
7h 34m
1 stop
$273Delta
Tue, Sep 1 - Sun, Sep 6
Delta Logo
9:24 am - 5:24 pm
MDW
-
YYZ
7h 00m
1 stop
Delta Logo
6:10 am - 9:17 am
YYZ
-
MDW
4h 07m
1 stop
$281Delta
Wed, Jul 1 - Tue, Jul 7
WestJet Logo
9:22 am - 5:29 pm
MDW
-
YYZ
7h 07m
1 stop
WestJet Logo
2:29 pm - 6:30 pm
YYZ
-
MDW
5h 01m
1 stop
$304WestJet
Tue, Aug 4 - Mon, Aug 17
Multiple Airlines Logo
10:20 am - 9:25 pm
MDW
-
YHZ
9h 05m
1 stop
Multiple Airlines Logo
8:30 am - 9:40 am
YHZ
-
MDW
27h 10m
1 stop
$394Multiple Airlines
Fri, Jul 3 - Sat, Jul 11
Multiple Airlines Logo
10:25 am - 11:22 pm
MDW
-
YHZ
10h 57m
1 stop
Multiple Airlines Logo
11:00 pm - 9:40 am
YHZ
-
MDW
12h 40m
1 stop
$414Multiple Airlines
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 5 days was to Toronto, at $195 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 5 days was $195.

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 $267 on average. Morning departures are around 2% cheaper than evening flights, on average. 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 $273.

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 $289, 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 March, when tickets cost $58 (return) on average. On the other hand, the most expensive months are October and January, when the average cost of round-trip tickets is $199 and $187 respectively.

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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.

Top tips for finding cheap flights to Canada

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Toronto $117 one-way - $247 round-trip

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 438 reviews
8.6Crew
8.0Comfort
8.2Boarding
7.6Food
6.9Entertainment
Airline reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

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..

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

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

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Five hour delays every hour, I wish it were all at once

Flight delayed four separate times. I’m now one hour hours late to landing.

worst flight ever from Delta, it got delayed and kept on delaying..

Should never have had to go to Detroit from Orlando back to Tennessee!

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

Two delays on two separate planes with parts they could not easily find and replace.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

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

Information on your arrival and departure airports