$106 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 7/8. 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, 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$219
Calgary
Calgary1 stop$354
Halifax
Halifax2 stops$384
Ottawa
Ottawa1 stop$408
Winnipeg
Winnipeg1 stop$374
Québec City
Québec City1 stop$535
St. John's
St. John's2 stops$621
Saskatoon
Saskatoon2 stops$513
Thunder Bay
Thunder Bay1 stop$494
Toronto
Torontononstop$219
Calgary
Calgary1 stop$354
Halifax
Halifax2 stops$384
Ottawa
Ottawa1 stop$408
Winnipeg
Winnipeg1 stop$374
Québec City
Québec City1 stop$535
St. John's
St. John's2 stops$621
Saskatoon
Saskatoon2 stops$513
Thunder Bay
Thunder Bay1 stop$494

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, Jul 30 - Mon, Aug 3
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
$219Porter Airlines
Mon, Jul 6 - Wed, Jul 8
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
$223Porter Airlines
Thu, Jul 2 - Tue, Aug 11
Porter Airlines Logo
10:25 am - 1:05 pm
MDW
-
YTZ
1h 40mnonstop
Porter Airlines Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
$224Porter Airlines
Wed, Jul 15 - 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
$225Porter Airlines
Fri, Jul 24 - Mon, Jul 27
KLM Logo
9:19 am - 5:24 pm
MDW
-
YYZ
7h 05m
1 stop
KLM Logo
12:09 pm - 6:25 pm
YYZ
-
MDW
7h 16m
1 stop
$266KLM
Wed, Sep 9 - Tue, Sep 15
Delta Logo
9:29 am - 5:20 pm
MDW
-
YYZ
6h 51m
1 stop
Delta Logo
6:00 am - 12:34 pm
YYZ
-
MDW
7h 34m
1 stop
$272Delta
Fri, Oct 2 - Sun, Oct 11
Delta Logo
9:30 am - 5:20 pm
MDW
-
YYZ
6h 50m
1 stop
Delta Logo
12:15 pm - 6:37 pm
YYZ
-
MDW
7h 22m
1 stop
$273Delta
Thu, Jul 2 - Mon, Jul 6
KLM Logo
1:26 pm - 11:02 pm
MDW
-
YYZ
8h 36m
1 stop
KLM Logo
12:09 pm - 6:31 pm
YYZ
-
MDW
7h 22m
1 stop
$279KLM
Tue, Jul 21 - Fri, Aug 7
Multiple Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
Multiple Airlines Logo
1:30 pm - 9:40 am
YHZ
-
MDW
22h 10m
1 stop
$384Multiple Airlines
Wed, Jul 29 - Fri, Aug 7
Multiple Airlines Logo
3:20 pm - 11:44 pm
MDW
-
YHZ
6h 24m
2 stops
Multiple Airlines Logo
1:30 pm - 9:40 am
YHZ
-
MDW
22h 10m
1 stop
$387Multiple 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 $207 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 $207.

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 $286, 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$106
Best time to beat the crowds with an average 31% 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
8.2Boarding
6.9Entertainment
7.6Food
8.6Crew
8.0Comfort
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

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

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

Information on your arrival and departure airports