$88 Find Cheap Flights from Canada to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 10/3. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Canada to Midway

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

Tue, Sep 9 - Sun, Sep 14
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$115Porter Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
Porter Airlines Logo
7:30 am - 8:19 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
$130Porter Airlines
Find Deal
Fri, Sep 5 - Mon, Sep 8
 Logo
7:30 am - 8:19 amYTZ-MDW
1h 49mnonstop
 Logo
9:15 am - 11:57 amMDW-YTZ
1h 42mnonstop
Wed, Jul 30 - Thu, Jul 31
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$167Air Transat
Find Deal
Wed, Jul 30 - Fri, Aug 1
Air Transat Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
$168Air Transat
Find Deal
Tue, Jul 15 - Sat, Jul 19
 Logo
7:55 am - 8:45 amYTZ-MDW
1h 50mnonstop
 Logo
9:40 am - 12:20 pmMDW-YTZ
1h 40mnonstop
Sat, Oct 4 - Wed, Oct 15
Delta Logo
12:14 pm - 6:35 pmYYZ-MDW
7h 21m1 stop
Delta Logo
2:00 pm - 10:55 pmMDW-YYZ
7h 55m1 stop
$214Delta
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Sat, Aug 16 - Wed, Aug 20
Delta Logo
12:14 pm - 6:37 pmYYZ-MDW
7h 23m1 stop
Delta Logo
9:31 am - 5:23 pmMDW-YYZ
6h 52m1 stop
$223Delta
Find Deal
Fri, Aug 15 - Fri, Aug 22
WestJet Logo
7:21 pm - 1:03 pmYYZ-MDW
18h 42m1 stop
WestJet Logo
12:43 pm - 9:58 pmMDW-YYZ
8h 15m1 stop
$256WestJet
Find Deal
Tue, Oct 14 - Sat, Oct 18
WestJet Logo
7:45 am - 9:44 pmYYZ-MDW
14h 59m1 stop
WestJet Logo
9:20 am - 8:52 pmMDW-YYZ
10h 32m2 stops
$264WestJet
Find Deal
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KAYAK's insights & trends for flights to Midway

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago Midway Airport, 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 to Chicago Midway Airport is May, where tickets cost $206 on average for return flights. On the other hand, the most expensive months are January and December, where the average cost of tickets from Canada is $322 and $277 respectively. For one-way flights, the best month to travel is July with an average price of $255.

What is a good deal for flights to Chicago Midway Airport?

If you’re looking for cheap airfare to Chicago Midway Airport, 25% of our users found tickets to Chicago Midway Airport for the following prices or less: From Toronto Island Airport $175 round-trip.


Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$88
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Island to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • How far is Chicago Midway Airport from central Chicago?

    You’ll need to travel 9 miles to reach the Chicago city center from Chicago Midway Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $194. The cheapest price found on KAYAK in the last 2 weeks cost $99 and departed from Toronto Island Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Monday where round-trip tickets can be as cheap as $247. On the other hand, the most expensive day to fly is Tuesday, where round-trip prices are $292 on average.

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

    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 to Chicago Midway Airport.

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

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

    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 Chicago Midway Airport 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 to Chicago Midway Airport?

    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 Chicago Midway Airport 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 Chicago Midway Airport?

    The cheapest time of day to fly to Chicago Midway Airport is generally in the evening, when round-trip flights cost $247 on average. The most expensive time of day to fly to Chicago Midway Airport is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $284.

  • How many direct flights to Chicago Midway Airport are there each week?

    Each week there are around 1,726 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Friday, with 15% of flights taking off on this day.

Top tips for finding cheap flights to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $104 or less one-way and $175 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago Midway Airport flight deals.

Reviews of the top airline flying from Canada to Midway

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Midway? 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 298 reviews
8.1Comfort
7.7Food
8.7Crew
7.0Entertainment
8.2Boarding
Airline reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

8.0 ExcellentChaim, Jul 2025YYZ - LGA
Read more Porter Airlines reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

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.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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