$117 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 5/27. 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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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, Apr 30 - Sun, May 3
Porter Airlines Logo
6:50 am - 10:15 am
YUL
-
MDW
4h 25m
1 stop
Porter Airlines Logo
10:30 am - 5:15 pm
MDW
-
YUL
5h 45m
1 stop
$175Porter Airlines
Fri, May 8 - Mon, May 11
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
3:20 pm - 10:10 pm
MDW
-
YUL
5h 50m
1 stop
$179Porter Airlines
Fri, May 8 - Mon, May 11
Porter Airlines Logo
6:30 am - 9:45 am
YUL
-
MDW
4h 15m
1 stop
Porter Airlines Logo
10:30 am - 6:15 pm
MDW
-
YUL
6h 45m
1 stop
$180Porter Airlines
Mon, May 4 - Thu, May 7
Multiple Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
10:30 am - 1:10 pm
MDW
-
YTZ
1h 40mnonstop
$198Multiple Airlines
Wed, May 6 - Fri, May 8
Air Transat Logo
1:45 pm - 2:35 pm
YTZ
-
MDW
1h 50mnonstop
Air Transat Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$199Air Transat
Sat, May 2 - Mon, May 4
Delta Logo
2:15 pm - 5:58 pm
YYZ
-
MDW
4h 43m
1 stop
Delta Logo
6:38 pm - 10:56 pm
MDW
-
YYZ
3h 18m
1 stop
$214Delta
Sun, May 10 - Sun, May 17
Delta Logo
6:10 am - 12:42 pm
YYZ
-
MDW
7h 32m
1 stop
Delta Logo
9:22 am - 5:21 pm
MDW
-
YYZ
6h 59m
1 stop
$223Delta
Tue, Apr 21 - Tue, Apr 28
Multiple Airlines Logo
3:35 pm - 1:00 pm
YOW
-
MDW
22h 25m
2 stops
Multiple Airlines Logo
7:30 am - 5:25 pm
MDW
-
YOW
8h 55m
1 stop
$320Multiple Airlines
Wed, Jun 17 - Mon, Jun 22
WestJet Logo
7:00 am - 6:18 pm
YWG
-
MDW
11h 18m
2 stops
WestJet Logo
1:16 pm - 12:55 am
MDW
-
YWG
11h 39m
2 stops
$504WestJet
Mon, Apr 20 - Mon, Apr 27
WestJet Logo
5:00 am - 5:58 pm
YWG
-
MDW
12h 58m
2 stops
WestJet Logo
9:27 am - 12:55 am
MDW
-
YWG
15h 28m
2 stops
$515WestJet
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 Montreal, at $175 return. The most popular connection is from Minneapolis to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $170 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as $215. On the other hand, the most expensive day to fly is Thursday, where round-trip prices are $297 on average.

What is the cheapest time of day to fly to Chicago Midway Airport?

The average price for all round-trip flights to Chicago Midway Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago Midway Airport is generally in the evening, when round-trip flights cost $237 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 $327.

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 $278 round-trip.

Good to know

Low seasonFebruary
Cheapest flight$117
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Montreal 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 Montreal, at $175 return. The most popular connection is from Minneapolis to Chicago Midway Airport and KAYAK users have found round-trip deals for as low as $170 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 $231. The cheapest price found on KAYAK in the last 2 weeks cost $104 and departed from Toronto Island Airport.

  • 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.

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 $127 or less one-way and $278 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 428 reviews
7.0Entertainment
8.0Comfort
8.6Crew
8.2Boarding
7.6Food
Airline reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

10.0 ExcellentDeanna, Mar 2026
YWG - YOW
Read more Porter Airlines reviews

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

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..

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

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.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

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.👍

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
Griffith
Saint John

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago