$110 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 12/3. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$184
Overall average: $292
Porter Airlines
Thu 12/11Sun 12/14
YTZ - MDW • Non-stop
Cheapest one-way
$110
Multiple Airlines
Wed 12/3
YVR - MDW • 1 stop
Top routes
YVR-MDW
Cheapest
YTZ-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 29% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight 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

Thu, Dec 11 - Sun, Dec 14
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$184Porter Airlines
Find Deal
Fri, Dec 5 - Thu, Dec 11
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$188Porter Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
Porter Airlines Logo
2:30 pm - 3:20 pmYTZ-MDW
1h 50mnonstop
Porter Airlines Logo
4:15 pm - 6:57 pmMDW-YTZ
1h 42mnonstop
$191Porter Airlines
Find Deal
Mon, Jan 5 - Mon, Jan 12
Delta Logo
7:45 am - 12:48 pmYYZ-MDW
6h 03m1 stop
Delta Logo
6:14 pm - 10:41 pmMDW-YYZ
3h 27m1 stop
$201Delta
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Sun, Dec 7 - Thu, Dec 11
Multiple Airlines Logo
11:00 pm - 10:12 pmYVR-MDW
21h 12m1 stop
Multiple Airlines Logo
7:23 pm - 3:45 pmMDW-YVR
22h 22m2 stops
$205Multiple Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Delta Logo
12:13 pm - 6:00 pmYYZ-MDW
6h 47m1 stop
Delta Logo
9:34 am - 2:48 pmMDW-YYZ
4h 14m1 stop
$210Delta
Find Deal
Thu, Dec 11 - Sun, Dec 14
KLM Logo
6:05 am - 12:34 pmYYZ-MDW
7h 29m1 stop
KLM Logo
9:34 am - 5:15 pmMDW-YYZ
6h 41m1 stop
$213KLM
Find Deal
Fri, Dec 5 - Mon, Dec 8
Multiple Airlines Logo
11:00 pm - 1:59 pmYVR-MDW
12h 59m1 stop
Multiple Airlines Logo
8:42 pm - 2:45 pmMDW-YVR
20h 03m2 stops
$215Multiple Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
WestJet Logo
6:30 am - 1:10 pmYYZ-MDW
7h 40m1 stop
WestJet Logo
1:50 pm - 11:27 pmMDW-YYZ
8h 37m1 stop
$275WestJet
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Tue, Dec 2 - Tue, Dec 9
WestJet Logo
6:30 pm - 9:54 amYYZ-MDW
16h 24m2 stops
WestJet Logo
10:49 am - 11:59 pmMDW-YYZ
12h 10m1 stop
$279WestJet
Find Deal
Booking Insights

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 flight to Chicago Midway Airport?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

The cheapest airline ticket to Chicago Midway Airport from the Canada in the last 72 hours was $110 one-way, and $184 round-trip on the route from Vancouver to Chicago Midway Airport. The most popular route is from Toronto to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $184 round-trip.

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 September, where tickets cost $154 on average for one-way flights. On the other hand, the most expensive months are October and July, where the average cost of tickets from Canada is $448 and $383 respectively. For return trips, the best month to travel is September with an average price of $172.

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 $189 one-way - $286 round-trip.

Good to know

Low seasonFebruary
Cheapest flight$110
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Vancouver to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    The cheapest airline ticket to Chicago Midway Airport from the Canada in the last 72 hours was $110 one-way, and $184 round-trip on the route from Vancouver to Chicago Midway Airport. The most popular route is from Toronto to Chicago Midway Airport and the cheapest ticket found on this route in the last 72 hours was $184 round-trip.

  • 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 $266. The cheapest price found on KAYAK in the last 2 weeks cost $163 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 Saturday where tickets can be as cheap as $228. On the other hand, the most expensive day to fly is Thursday, where prices are $294 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 flights cost $240 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 $333.

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 $189 or less one-way and $286 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 387 reviews
8.2Boarding
7.6Food
8.0Comfort
7.0Entertainment
8.6Crew
Airline reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

8.0 ExcellentPilar, Oct 2025FLL - YOW
Read more Porter Airlines reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

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

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

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.

Traveling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Chesterton
Schererville
Munster
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago

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