MDW

C$ 166 Find Cheap Flights to Chicago

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 11/2. 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
C$ 246
Overall average: C$ 282
Porter Airlines
Thu 22/1Sun 25/1
YTZ - MDW • Direct
Cheapest one-way flights
C$ 166
Typical prices: C$ 246-C$ 303
Porter Airlines
Wed 11/2
YTZ - MDW • Direct
When to travel
September
Cheapest • 29% 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 hundreds 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 to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights 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 to Midway

Thu, 22 Jan - Sun, 25 Jan
Porter Airlines Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 246Porter Airlines
Fri, 20 Feb - Mon, 23 Feb
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 248Porter Airlines
Fri, 20 Feb - Mon, 23 Feb
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 249Porter Airlines
Thu, 29 Jan - Sun, 1 Feb
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 259Porter Airlines
Sun, 1 Feb - Tue, 3 Feb
Delta Logo
12:12 p.m. - 5:55 p.m.
YYZ
-
MDW
6h 43m1 stop
Delta Logo
1:26 p.m. - 7:08 p.m.
MDW
-
YYZ
4h 42m1 stop
C$ 293Delta
Sun, 1 Feb - Wed, 4 Feb
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
Delta Logo
9:53 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 06m1 stop
C$ 295Delta
Tue, 6 Jan - Tue, 13 Jan
WestJet Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
WestJet Logo
9:50 a.m. - 3:59 p.m.
MDW
-
YYZ
5h 09m1 stop
C$ 360WestJet
Sun, 25 Jan - Sun, 1 Feb
Multiple Airlines Logo
11:00 p.m. - 11:45 a.m.
YVR
-
MDW
10h 45m1 stop
Multiple Airlines Logo
7:30 a.m. - 10:20 p.m.
MDW
-
YVR
16h 50m2 stops
C$ 368Multiple Airlines
Sat, 24 Jan - Sat, 7 Feb
Multiple Airlines Logo
9:00 p.m. - 10:19 p.m.
YWG
-
MDW
25h 19m2 stops
Multiple Airlines Logo
9:38 a.m. - 3:09 p.m.
MDW
-
YWG
29h 31m1 stop
C$ 383Multiple Airlines
Tue, 14 Apr - Wed, 22 Apr
WestJet Logo
6:00 a.m. - 6:31 p.m.
YQR
-
MDW
11h 31m2 stops
WestJet Logo
10:35 a.m. - 12:15 a.m.
MDW
-
YQR
14h 40m2 stops
C$ 681WestJet
Booking Insights

KAYAK's insights & trends for flights to Midway

Get data-powered insights and trends into flights to Midway to help you find the cheapest flights, the best time to fly and much more.

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 C$ 213 on average for one-way flights. On the other hand, the most expensive months are October and November, where the average cost of tickets from Canada is C$ 747 and C$ 648 respectively. For return trips, the best month to travel is September with an average price of C$ 238.

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 C$ 153 one-way - C$ 245 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonNovember
Cheapest flightC$ 166
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights to Midway

Are your dates flexible? Find out the best times to travel to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • How far is Chicago Midway Airport from central Chicago?

    The distance between Chicago Midway Airport and downtown Chicago is 14 km.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs C$ 243. The cheapest price found on KAYAK in the last 2 weeks cost C$ 120 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 Friday where tickets can be as cheap as C$ 311. On the other hand, the most expensive day to fly is Sunday, where prices are C$ 341 on average.

  • How does KAYAK find such low prices on flights to Chicago?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    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 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?

    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 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 morning, when flights cost C$ 294 on average. The most expensive time of day to fly to Chicago Midway Airport is generally at night, which is peak travel time and where the average cost of a ticket is C$ 671.

Top tips for finding cheap flights to Chicago

  • Looking for cheap airfare to Chicago? 25% of our users found round-trip tickets to Chicago for the following prices or less: From Toronto Island C$ 199
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top airlines flying 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 397 reviews
8.0Comfort
8.2Boarding
8.6Crew
7.0Entertainment
7.6Food
Airline reviews

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

4.0 OkayAnonymous, Dec 2025
YTZ - YUL
Read more Porter Airlines reviews

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

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

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

Very good. A lot better experience then I expected for an economy flight.

It was very good but no tv but the experience was great

Thank you for making my first experience very enjoyable. You made it all very pleasant

Great flight great seats will absolutely fly with you again

Porter airlines was good. I didn't have the best experience when booking through airfare assist however, as I got no final confirmation from them that the flight was booked until I called them. Even then, the confirmation code they gave me was incorrect and couldn't be used for check in. On a positive note airfare assist was actually picked up the phone relatively quickly when calling

The flight crew were very good, polite, and professional. Unfortunately, the rest of the experience left much to be desired. The food was extremely bland—almost tasteless. We chose the non vegetarian .The lasagna was just plain pasta with a tiny garnish and no seasoning. It felt like eating starch only, The bigger issue was with luggage and space. We boarded with three tickets, and while the seats in front of us were nearly empty, all the overhead compartments had already been filled by passengers boarding to the back. This left us and many others with no overhead storage for our carry-ons. Our bags couldn’t fit well under the seats either, which meant we lost the little legroom we had. The result was a horrible, cramped experience—sore knees, no space to stretch, and no way to rest or sleep comfortably. According to the crew this was a rather normal thing. It is obviously normal that people board with handbag and carry on but they should be only allowed to use their overhead compartment and under their seat not the way it is managed that all the spaces in the front of the plane being occupied by the people sitting way back in the plane.

Nice complete meal included and great services. Plus the plane was very clean.

Everything was horrible. On the day of my departure, I was denied check-in and boarding because my reservation only showed one of my last names, while my passport contains both. This minor discrepancy could have been easily corrected, but I was informed that no adjustment could be made. As a result, I lost not only my outbound flight but also my return flight and had to purchase a new ticket at a significantly higher cost.

Travelling to a place near Midway?

Book flights to Midway if you plan to visit one of these locations
Munster
Benton Harbor
New Buffalo
Merrillville
Portage
Schererville
Hammond
Crown Point
Saint Joseph
Chesterton
Valparaiso
Monticello
Porter

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago