MDW

C$ 179 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 26/6. 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$ 281
Typical prices: C$ 505-C$ 246
Porter Airlines
Tue 30/6Tue 7/7
YTZ - MDW • Direct
Cheapest one-way flights
C$ 181
Porter Airlines
Fri 26/6
YTZ - MDW • Direct
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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

Tue, 30 Jun - Tue, 7 Jul
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
3:20 p.m. - 6:00 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 281Porter Airlines
Fri, 26 Jun - Thu, 2 Jul
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 282Porter Airlines
Mon, 22 Jun - Thu, 25 Jun
Porter Airlines Logo
8:50 a.m. - 9:40 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 284Porter Airlines
Mon, 15 Jun - Tue, 23 Jun
Porter Airlines Logo
8:45 a.m. - 9:35 a.m.
YTZ
-
MDW
1h 50mdirect
Porter Airlines Logo
10:25 a.m. - 1:05 p.m.
MDW
-
YTZ
1h 40mdirect
C$ 285Porter Airlines
Fri, 25 Sep - Mon, 28 Sep
Delta Logo
4:05 p.m. - 6:33 p.m.
YYZ
-
MDW
3h 28m
1 stop
Delta Logo
9:30 a.m. - 5:20 p.m.
MDW
-
YYZ
6h 50m
1 stop
C$ 363Delta
Thu, 25 Jun - Sat, 27 Jun
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
9:17 a.m. - 3:19 p.m.
MDW
-
YYZ
5h 02m
1 stop
C$ 364Delta
Tue, 1 Sep - Fri, 4 Sep
WestJet Logo
9:50 a.m. - 5:04 p.m.
YYZ
-
MDW
8h 14m
1 stop
WestJet Logo
1:32 p.m. - 11:04 p.m.
MDW
-
YYZ
8h 32m
1 stop
C$ 370WestJet
Thu, 18 Jun - Sun, 21 Jun
Undisclosed Carrier Logo
12:14 p.m. - 6:36 p.m.
YYZ
-
MDW
7h 22m
1 stop
Undisclosed Carrier Logo
9:22 a.m. - 5:29 p.m.
MDW
-
YYZ
7h 07m
1 stop
C$ 392Undisclosed Carrier
Wed, 1 Jul - Wed, 8 Jul
Multiple Airlines Logo
5:15 p.m. - 9:40 a.m.
YWG
-
MDW
16h 25m
1 stop
Multiple Airlines Logo
10:25 a.m. - 7:25 p.m.
MDW
-
YWG
9h 00m
1 stop
C$ 577Multiple Airlines
Wed, 30 Sep - Mon, 5 Oct
Multiple Airlines Logo
10:55 p.m. - 10:58 a.m.
YVR
-
MDW
10h 03m
1 stop
Multiple Airlines Logo
7:25 a.m. - 7:10 p.m.
MDW
-
YVR
13h 45m
2 stops
C$ 615Multiple Airlines
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 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 Monday where round-trip tickets can be as cheap as C$ 294. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are C$ 320 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 morning, when round-trip flights cost C$ 302 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$ 674.

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$ 294 round-trip.

Good to know – Book Cheap Chicago Midway Airport Plane Tickets

Low seasonFebruary
Cheapest flightC$ 181
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 16% 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$ 313. The cheapest price found on KAYAK in the last 2 weeks cost C$ 174 and departed from Toronto Island Airport.

  • 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.

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$ 250
  • 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 440 reviews
8.2Boarding
7.6Food
8.6Crew
6.9Entertainment
8.0Comfort
Airline reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

10.0 ExcellentAngela, May 2026
YYZ - YVR
Read more Porter Airlines reviews

The staff was amazing. Best service I’ve had on an aircraft in a long time. Was not particularly happy with the food. Flight was at 10:50 and left home too early for breakfast and wasn’t able to purchase food at airport and felt for sure I could get some breakfast to buy on airplane. Nope as food was served around 11:30 and only one choice left (I was at 22C) so ordered the chicken dish thinking I’m getting a hot meal but cold chicken with rice and carrots etc. I was looking forward to a croissant sandwich and a hot cup of tea. The FA was kind to explain they were serving dinner at that time. She was lovely Other than the disappointment with the food the staff was amazing. On my return flight I will make sure to eat and take some food with me so I’m not hungry or disappointed. This was my second time ever flying Porter and will consider checking them when I next come to visit my daughter. Have to say it again best crew I’ve ever experienced on a flight and I travel quite a bit. Thanks.

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

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.

The dinner was bland and boring, but the economy seats were surprisingly comfortable. The flight was very packed.

Arm rests are too small and too close. No screens, movie selection was very limited and poor. Food is pretty much overpriced cheap convenience store food.

I didn't have any problems during my flight. My main issue is with airlines in general, they keep offering less and less every year, AirTransat is no different.

i was not able to take my flight because the information i needed to book my dog correctly was not provided

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

They never sent me a confirmation to say my flight time had changed so I cut my holiday short by 6 hours Had to pay over 50 American for my luggage to be checked on the way home and that’s more that it cost on the way there. Arbitrarily charging more for the same thing when the passenger has no options is shady The cabin was an icebox going there and back, if all the passengers have their gloves on and their hoods up that should be an obvious sign to turn up the heat

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

The on-board crew were professional and friendly and made the trip feel like we were taken care of well. The gate for the flight departure changed three times...not great but not terrible. Considering it was the day of the New Jalisco Cartel mayhem, we can't really complain.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

Travelling to a place near Midway?

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

Everything you need to know for your flight to Midway

Information on the airport you'll fly into in Chicago