MDW

Find First Class Flights to Chicago Midway Airport

1 adult
1 adult, First, 0 bags

KAYAK searches hundreds of travel sites at once for deals on first class 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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Cheap First Class Flight Deals to Chicago Midway Airport

 
These are the cheapest deals for flights from Canada to Chicago Midway Airport currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 first class round-trip flight deals to Chicago Midway Airport

Thu, 26 Mar - Mon, 30 Mar
Delta Logo
6:45 a.m. - 5:54 p.m.
YUL
-
MDW
12h 09m
2 stops
Delta Logo
2:05 p.m. - 11:40 p.m.
MDW
-
YUL
8h 35m
1 stop
C$ 998Delta
Tue, 17 Feb - Fri, 20 Feb
Delta Logo
6:20 a.m. - 5:37 p.m.
YVR
-
MDW
9h 17m
2 stops
Delta Logo
9:50 a.m. - 6:47 p.m.
MDW
-
YVR
10h 57m
2 stops
C$ 1,525Delta
Sun, 1 Mar - Thu, 5 Mar
Delta Logo
6:45 a.m. - 5:37 p.m.
YUL
-
MDW
11h 52m
2 stops
Delta Logo
6:00 a.m. - 4:53 p.m.
MDW
-
YUL
9h 53m
1 stop
C$ 1,586Delta
Fri, 15 May - Fri, 22 May
Delta Logo
6:40 a.m. - 1:07 p.m.
YWG
-
MDW
6h 27m
1 stop
Delta Logo
2:00 p.m. - 8:09 p.m.
MDW
-
YWG
6h 09m
1 stop
C$ 1,623Delta
Wed, 18 Feb - Sat, 21 Feb
Delta Logo
7:37 p.m. - 8:54 a.m.
YVR
-
MDW
11h 17m
2 stops
Delta Logo
9:34 a.m. - 9:00 p.m.
MDW
-
YVR
13h 26m
2 stops
C$ 1,625Delta
Wed, 11 Mar - Mon, 16 Mar
Delta Logo
11:00 p.m. - 9:56 a.m.
YVR
-
MDW
8h 56m
1 stop
Delta Logo
9:30 a.m. - 6:43 p.m.
MDW
-
YVR
11h 13m
2 stops
C$ 1,692Delta
Thu, 19 Feb - Sun, 22 Feb
Delta Logo
4:55 p.m. - 9:06 a.m.
YVR
-
MDW
14h 11m
2 stops
Delta Logo
9:34 a.m. - 9:00 p.m.
MDW
-
YVR
13h 26m
2 stops
C$ 1,712Delta
Wed, 11 Mar - Sun, 15 Mar
Delta Logo
11:00 p.m. - 9:56 a.m.
YVR
-
MDW
8h 56m
1 stop
Delta Logo
9:35 a.m. - 8:55 p.m.
MDW
-
YVR
13h 20m
2 stops
C$ 1,924Delta
Wed, 11 Mar - Sun, 15 Mar
Delta Logo
11:00 p.m. - 9:56 a.m.
YVR
-
MDW
8h 56m
1 stop
Delta Logo
9:35 a.m. - 8:55 p.m.
MDW
-
YVR
13h 20m
2 stops
C$ 1,972Delta
Mon, 16 Feb - Thu, 19 Feb
Delta Logo
7:37 p.m. - 8:54 a.m.
YVR
-
MDW
11h 17m
2 stops
Delta Logo
9:50 a.m. - 6:43 p.m.
MDW
-
YVR
10h 53m
2 stops
C$ 2,018Delta

When to book first class flights to Chicago Midway Airport

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago Midway Airport, so you can find the best time to fly.
Average price per month
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

FAQs for Chicago Midway Airport first class flights

  • How long is a flight to Chicago Midway Airport?

    Flights from Toronto1h 45m
  • What is the most popular airline offering First Class flights to Chicago Midway Airport?

    Among KAYAK users, Delta is the most popular airline offering First Class seats on flights to Chicago Midway Airport.

  • Which airlines offer First Class tickets on flights to Chicago Midway Airport?

    Traveling to Chicago Midway Airport and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: Delta.

  • How does KAYAK find such good deals on First Class tickets to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can 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 for economy class as well as First Class travelers.

  • What is the best airline for first class flights to Chicago Midway Airport?

    The highest-rated airline by KAYAK users offering first class flights to Chicago Midway Airport is Porter Airlines, with an overall rating of 7.9.

Reviews of the top airlines flying to Chicago Midway Airport

 
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 first class to Chicago Midway Airport? 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 412 reviews
8.2Boarding
7.5Food
8.6Crew
7.9Comfort
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.👍

The Turkish was good . I had a problem with air Transat terrible experience for me

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 you need to know for your flight to Chicago Midway Airport

Information on the airport you'll fly into in Chicago Midway Airport