MDW

C$ 135 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 19/2. 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$ 249
Overall average: C$ 321
Multiple Airlines
Fri 20/2Sun 22/2
YTZ - MDW • Direct
Cheapest one-way flights
C$ 135
Porter Airlines
Thu 19/2
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 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

Fri, 20 Feb - Sun, 22 Feb
Multiple Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 249Multiple Airlines
Tue, 3 Feb - Tue, 10 Feb
Air Transat Logo
9:20 a.m. - 10:10 a.m.
YTZ
-
MDW
1h 50mdirect
Air Transat Logo
11:05 a.m. - 1:47 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 252Air Transat
Sat, 31 Jan - Mon, 2 Feb
Porter Airlines Logo
11:00 a.m. - 11:50 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 255Porter Airlines
Sun, 8 Feb - Tue, 10 Feb
Multiple Airlines Logo
2:30 p.m. - 3:20 p.m.
YTZ
-
MDW
1h 50mdirect
Multiple Airlines Logo
11:00 a.m. - 1:42 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 256Multiple Airlines
Thu, 22 Jan - Fri, 23 Jan
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$ 258Porter Airlines
Fri, 13 Mar - Sun, 15 Mar
Porter Airlines Logo
9:15 a.m. - 10:05 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
4:15 p.m. - 6:57 p.m.
MDW
-
YTZ
1h 42mdirect
C$ 259Porter Airlines
Tue, 3 Feb - Tue, 10 Feb
Delta Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
Delta Logo
6:35 p.m. - 10:42 p.m.
MDW
-
YYZ
3h 07m1 stop
C$ 285Delta
Thu, 5 Feb - Sun, 8 Feb
Delta Logo
10:05 a.m. - 12:46 p.m.
YYZ
-
MDW
3h 41m1 stop
Delta Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
C$ 298Delta
Thu, 5 Feb - Sun, 8 Feb
KLM Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
KLM Logo
9:33 a.m. - 4:12 p.m.
MDW
-
YYZ
5h 39m1 stop
C$ 379KLM
Wed, 11 Feb - Wed, 11 Feb
WestJet Logo
6:00 a.m. - 8:52 a.m.
YYZ
-
MDW
3h 52m1 stop
WestJet Logo
6:35 p.m. - 9:02 a.m.
MDW
-
YYZ
13h 27m1 stop
C$ 382WestJet
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 flight to Chicago?

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 was found on the route from Montreal, at C$ 135 one-way and C$ 249 round-trip. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as C$ 249 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 September, where tickets cost C$ 212 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 C$ 763 and C$ 744 respectively. For return trips, the best month to travel is September with an average price of C$ 237.

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$ 197 one-way - C$ 287 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonJanuary
Cheapest flightC$ 135
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

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

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Montreal, at C$ 135 one-way and C$ 249 round-trip. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as C$ 249 in the last 3 days.

  • 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$ 368. The cheapest price found on KAYAK in the last 2 weeks cost C$ 174 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 Monday where tickets can be as cheap as C$ 271. On the other hand, the most expensive day to fly is Wednesday, where prices are C$ 302 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 evening, when flights cost C$ 288 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$ 668.

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$ 242
  • 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 406 reviews
7.6Food
8.6Crew
7.0Entertainment
8.2Boarding
7.9Comfort
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

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
Merrillville
Schererville
Valparaiso
Portage
Hammond
New Buffalo
Crown Point
Saint Joseph
Chesterton
Monticello
Porter

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago