$98 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 2/19. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$181
Overall average: $233
Multiple Airlines
Fri 2/20Sun 2/22
YTZ - MDW • Non-stop
Cheapest one-way
$98
Porter Airlines
Thu 2/19
YUL - MDW • 1 stop
Top routes
YUL-MDW
Cheapest
YTZ-MDW
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 27% price drop
August
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Fri, Feb 20 - Sun, Feb 22
Multiple Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
4:15 pm - 6:57 pm
MDW
-
YTZ
1h 42mnonstop
$181Multiple Airlines
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
4:15 pm - 6:57 pm
MDW
-
YTZ
1h 42mnonstop
$183Multiple Airlines
Sat, Feb 21 - Sat, Feb 28
Porter Airlines Logo
11:00 am - 11:50 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
12:45 pm - 3:27 pm
MDW
-
YTZ
1h 42mnonstop
$184Porter Airlines
Sat, Jan 31 - Mon, Feb 2
Porter Airlines Logo
11:00 am - 11:50 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$185Porter Airlines
Sun, Feb 8 - Tue, Feb 10
Multiple Airlines Logo
2:30 pm - 3:20 pm
YTZ
-
MDW
1h 50mnonstop
Multiple Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$186Multiple Airlines
Thu, Jan 22 - Fri, Jan 23
Porter Airlines Logo
9:15 am - 10:05 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$187Porter Airlines
Tue, Feb 3 - Tue, Feb 10
Delta Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
Delta Logo
6:35 pm - 10:42 pm
MDW
-
YYZ
3h 07m1 stop
$207Delta
Thu, Feb 5 - Sun, Feb 8
Delta Logo
10:05 am - 12:46 pm
YYZ
-
MDW
3h 41m1 stop
Delta Logo
9:33 am - 4:12 pm
MDW
-
YYZ
5h 39m1 stop
$216Delta
Thu, Feb 5 - Sun, Feb 8
KLM Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
KLM Logo
9:33 am - 4:12 pm
MDW
-
YYZ
5h 39m1 stop
$275KLM
Wed, Feb 11 - Wed, Feb 11
WestJet Logo
6:00 am - 8:52 am
YYZ
-
MDW
3h 52m1 stop
WestJet Logo
6:35 pm - 9:02 am
MDW
-
YYZ
13h 27m1 stop
$277WestJet
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 $98 one-way, and $181 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 $181 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 January and October, where the average cost of tickets from Canada is $554 and $540 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 $212 one-way - $216 round-trip.

Good to know

Low seasonJanuary
Cheapest flight$98
Best time to beat the crowds but there is an average 44% increase in price.
Most popular time to fly and prices are also 7% lower on average.
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 $98 one-way, and $181 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 $181 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 $256. The cheapest price found on KAYAK in the last 2 weeks cost $110 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 $217. On the other hand, the most expensive day to fly is Thursday, where prices are $291 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 $231 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.

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 $212 or less one-way and $216 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 406 reviews
7.9Comfort
7.6Food
7.0Entertainment
8.6Crew
8.2Boarding
Airline reviews

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.

6.0 GoodJen, Jan 2026
YTZ - BOS
Read more Porter Airlines reviews

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.👍

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

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