$70 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 10/15. 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

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Flight Deals

Cheap Flights from Midway to Canada

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Toronto
Torontononstop$230
Calgary
Calgary1 stop$251
Halifax
Halifax1 stop$208
Ottawa
Ottawa1 stop$282
Québec City
Québec City1 stop$171
Winnipeg
Winnipeg1 stop$344
St. John's
St. John's1 stop$470
Saskatoon
Saskatoon2 stops$400
Thunder Bay
Thunder Bay2 stops$424
Toronto
Torontononstop$230
Calgary
Calgary1 stop$251
Halifax
Halifax1 stop$208
Ottawa
Ottawa1 stop$282
Québec City
Québec City1 stop$171
Winnipeg
Winnipeg1 stop$344
St. John's
St. John's1 stop$470
Saskatoon
Saskatoon2 stops$400
Thunder Bay
Thunder Bay2 stops$424

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

Sat, Oct 18 - Thu, Oct 23
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$171Porter Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$173Porter Airlines
Find Deal
Mon, Oct 6 - Fri, Oct 17
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$175Porter Airlines
Find Deal
Tue, Oct 14 - Fri, Oct 17
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
$183Porter Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Multiple Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
Multiple Airlines Logo
12:00 pm - 9:47 amYTZ-MDW
22h 47m2 stops
$230Multiple Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Multiple Airlines Logo
6:25 am - 12:15 amMDW-YVR
19h 50m2 stops
Multiple Airlines Logo
11:00 pm - 6:39 pmYVR-MDW
17h 39m1 stop
$236Multiple Airlines
Find Deal
Tue, Sep 30 - Fri, Oct 3
Delta Logo
1:43 pm - 8:42 pmMDW-YYC
7h 59m1 stop
Delta Logo
6:40 am - 5:35 pmYYC-MDW
9h 55m1 stop
$251Delta
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Sat, Nov 8 - Sat, Nov 15
Delta Logo
1:06 pm - 11:02 pmMDW-YYC
10h 56m2 stops
Delta Logo
6:20 am - 1:07 pmYYC-MDW
5h 47m1 stop
$261Delta
Find Deal
Sat, Nov 1 - Sat, Nov 8
WestJet Logo
9:20 am - 3:59 pmMDW-YYZ
5h 39m1 stop
WestJet Logo
6:20 am - 1:08 pmYYZ-MDW
7h 48m1 stop
$277WestJet
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Wed, Nov 19 - Fri, Nov 21
WestJet Logo
10:47 am - 5:00 pmMDW-YYZ
5h 13m1 stop
WestJet Logo
6:10 pm - 9:53 amYYZ-MDW
16h 43m1 stop
$290WestJet
Find Deal
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 $75 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 $75.

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 $246, 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 March and June, when the average cost of round-trip tickets is $381 and $371 respectively.

Good to know

Low seasonMarch
Cheapest flight$70
Best time to beat the crowds but there is an average 68% increase in price.
Most popular time to fly and prices are also 32% lower on average.
Flight from Chicago Midway Airport to Québec City

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.

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

    The cheapest time of day to fly to Canada is generally in the evening, when round-trip flights cost $273 on average. Morning departures are around 1% more expensive than evening flights, on average. The most expensive time of day to fly to Canada is generally at night, which is peak travel time and where the average cost of a ticket is $360.

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 $88 one-way - $196 round-trip

Reviews of the top airline 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.
7.9
Porter AirlinesOverall score based on 365 reviews
8.2Boarding
7.0Entertainment
7.6Food
7.9Comfort
8.6Crew
Airline reviews

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.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

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.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

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.

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

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

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