$97 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 9/26. 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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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

Fri, Sep 19 - Mon, Sep 22
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
$135Porter Airlines
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Thu, Sep 11 - Sat, Sep 13
Porter Airlines Logo
11:00 am - 4:24 pmYQB-MDW
6h 24m1 stop
Porter Airlines Logo
9:35 am - 3:55 pmMDW-YQB
5h 20m1 stop
$139Porter Airlines
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Sun, Oct 5 - Mon, Oct 6
Air Transat Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$212Air Transat
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Tue, Oct 7 - Sun, Oct 12
Delta Logo
12:15 pm - 6:25 pmYYZ-MDW
7h 10m1 stop
Delta Logo
9:35 am - 2:45 pmMDW-YYZ
4h 10m1 stop
$212Delta
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Wed, Oct 22 - Tue, Oct 28
Delta Logo
7:00 am - 4:09 pmYUL-MDW
10h 09m1 stop
Delta Logo
6:23 pm - 11:14 pmMDW-YUL
3h 51m1 stop
$215Delta
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Thu, Sep 18 - Sat, Sep 20
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$216Air Transat
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Thu, Oct 2 - Thu, Oct 9
Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$222
Find Deal
Thu, Sep 11 - Mon, Sep 15
Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$224
Find Deal
Tue, Sep 16 - Tue, Sep 23
WestJet Logo
7:45 am - 9:36 pmYYZ-MDW
14h 51m1 stop
WestJet Logo
9:20 am - 12:31 amMDW-YYZ
14h 11m2 stops
$265WestJet
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Wed, Oct 1 - Fri, Oct 3
WestJet Logo
1:20 pm - 9:36 pmYYZ-MDW
9h 16m1 stop
WestJet Logo
7:15 pm - 6:03 pmMDW-YYZ
21h 48m2 stops
$266WestJet
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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.

In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Québec City, at $135 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $172 in the last 3 days.

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 September with an average price of $155.

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 $182 round-trip.

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Good to know

Low seasonFebruary
Cheapest flight$97
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 4% lower on average.
Flight from Québec City to Chicago Midway Airport

FAQs - booking Chicago Midway Airport flights

  • What is the cheapest flight to Chicago Midway Airport?

    In the last 3 days, the cheapest flight deal to Chicago Midway Airport was found on the route from Québec City, at $135 return. The most popular connection is from Toronto to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $172 in the last 3 days.

  • 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 $226. The cheapest price found on KAYAK in the last 2 weeks cost $101 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 Wednesday where round-trip tickets can be as cheap as $228. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $288 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 $238 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 1,586 direct flights from within Canada to Chicago Midway Airport. The most common day for departures is Sunday, with 18% 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 $153 or less one-way and $182 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 336 reviews
8.2Boarding
8.7Crew
7.0Entertainment
7.6Food
8.0Comfort
Airline reviews

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.

8.0 ExcellentStephanie, Aug 2025YYZ - LGA
Read more Porter Airlines reviews

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.

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

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.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

Traveling to a place near Midway?

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

Chicago Midway Airport (MDW)

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