$116 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 3/29. 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
$167
Porter Airlines
Thu 4/16Sun 4/19
YUL - MDW • 1 stop
Cheapest non-stop
$193
Typical prices: $189-$226
Porter Airlines
Wed 3/18Wed 3/25
YTZ - MDW • Non-stop
Top routes
YUL
-
MDW
Cheapest
YTZ
-
MDW
Most popular
Insights
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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, Apr 16 - Sun, Apr 19
Porter Airlines Logo
6:45 am - 10:05 am
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
$167Porter Airlines
Sat, Apr 18 - Mon, Apr 20
Porter Airlines Logo
8:55 am - 11:50 am
YUL
-
MDW
3h 55m
1 stop
Porter Airlines Logo
4:15 pm - 10:45 pm
MDW
-
YUL
5h 30m
1 stop
$169Porter Airlines
Thu, Apr 16 - Sun, Apr 19
Porter Airlines Logo
6:45 am - 10:05 am
YUL
-
MDW
4h 20m
1 stop
Porter Airlines Logo
11:00 am - 5:45 pm
MDW
-
YUL
5h 45m
1 stop
$171Porter Airlines
Fri, May 8 - Mon, May 11
Porter Airlines Logo
6:30 am - 9:40 am
YUL
-
MDW
4h 10m
1 stop
Porter Airlines Logo
10:25 am - 5:15 pm
MDW
-
YUL
5h 50m
1 stop
$173Porter Airlines
Tue, Mar 31 - Tue, Apr 7
Delta Logo
6:30 am - 1:25 pm
YYC
-
MDW
5h 55m
1 stop
Delta Logo
2:05 pm - 8:45 pm
MDW
-
YYC
7h 40m
1 stop
$231Delta
Sat, May 23 - Fri, May 29
Delta Logo
12:09 pm - 6:14 pm
YYZ
-
MDW
7h 05m
1 stop
Delta Logo
6:36 pm - 10:59 pm
MDW
-
YYZ
3h 23m
1 stop
$242Delta
Thu, Apr 16 - Mon, Apr 20
Multiple Airlines Logo
5:15 pm - 8:04 am
YYZ
-
MDW
15h 49m
1 stop
Multiple Airlines Logo
9:14 am - 12:14 am
MDW
-
YYZ
14h 00m
1 stop
$288Multiple Airlines
Sun, Mar 22 - Sun, Mar 29
WestJet Logo
10:05 am - 12:29 pm
YYZ
-
MDW
3h 24m
1 stop
WestJet Logo
9:35 am - 5:17 pm
MDW
-
YYZ
6h 42m
1 stop
$291WestJet
Wed, Jun 3 - Mon, Jun 8
Multiple Airlines Logo
6:25 pm - 9:40 am
YOW
-
MDW
16h 15m
1 stop
Multiple Airlines Logo
5:35 pm - 5:35 pm
MDW
-
YOW
23h 00m
1 stop
$312Multiple Airlines
Wed, Jun 3 - Sat, Jun 6
WestJet Logo
5:55 am - 6:14 pm
YOW
-
MDW
13h 19m
2 stops
WestJet Logo
6:36 pm - 5:35 pm
MDW
-
YOW
21h 59m
2 stops
$410WestJet
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 $116 one-way, and $167 round-trip on the route from Montreal 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 $191 round-trip.

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 $122 one-way - $195 round-trip.

Good to know

Low seasonFebruary
Cheapest flight$116
Best time to beat the crowds but there is an average 23% increase 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?

    The cheapest airline ticket to Chicago Midway Airport from the Canada in the last 72 hours was $116 one-way, and $167 round-trip on the route from Montreal 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 $191 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 $309. The cheapest price found on KAYAK in the last 2 weeks cost $108 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 tickets can be as cheap as $208. 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 $230 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 $320.

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 $122 or less one-way and $195 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.
7.9
Porter AirlinesOverall score based on 416 reviews
8.2Boarding
7.5Food
7.9Comfort
8.6Crew
6.9Entertainment
Airline reviews

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..

6.0 GoodBeat, Jan 2026
YUL - YVR
Read more Porter Airlines reviews

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.

Much roomer than air Canada! Great flight for the price. No complaints

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