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, 5 Feb - Mon, 9 Feb
Delta Logo
7:45 a.m. - 12:46 p.m.
YYZ
-
MDW
6h 01m1 stop
Delta Logo
1:51 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 22m1 stop
C$ 502Delta
Wed, 31 Dec - Wed, 7 Jan
Delta Logo
12:09 p.m. - 5:26 p.m.
YYZ
-
MDW
6h 17m1 stop
Delta Logo
1:49 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 24m1 stop
C$ 931Delta
Tue, 30 Dec - Mon, 5 Jan
Delta Logo
9:54 a.m. - 5:26 p.m.
YYZ
-
MDW
8h 32m1 stop
Delta Logo
1:49 p.m. - 11:13 p.m.
MDW
-
YYZ
8h 24m1 stop
C$ 986Delta
Tue, 5 May - Sat, 16 May
Delta Logo
6:00 a.m. - 5:54 p.m.
YEG
-
MDW
10h 54m2 stops
Delta Logo
1:00 p.m. - 9:10 p.m.
MDW
-
YEG
9h 10m2 stops
C$ 1,109Delta
Tue, 13 Jan - Tue, 20 Jan
Delta Logo
7:37 p.m. - 8:52 a.m.
YVR
-
MDW
11h 15m2 stops
Delta Logo
1:49 p.m. - 11:59 p.m.
MDW
-
YVR
12h 10m2 stops
C$ 1,170Delta
Wed, 21 Jan - Fri, 23 Jan
Delta Logo
11:00 p.m. - 11:59 a.m.
YVR
-
MDW
10h 59m1 stop
Delta Logo
1:26 p.m. - 11:59 p.m.
MDW
-
YVR
12h 33m2 stops
C$ 1,219Delta
Wed, 14 Jan - Wed, 21 Jan
Delta Logo
7:37 p.m. - 8:52 a.m.
YVR
-
MDW
11h 15m2 stops
Delta Logo
1:49 p.m. - 11:59 p.m.
MDW
-
YVR
12h 10m2 stops
C$ 1,314Delta
Wed, 31 Dec - Sun, 4 Jan
Delta Logo
6:00 a.m. - 11:06 a.m.
YYZ
-
MDW
6h 06m1 stop
Delta Logo
6:08 p.m. - 9:04 a.m.
MDW
-
YYZ
13h 56m1 stop
C$ 1,416Delta
Mon, 29 Dec - Tue, 6 Jan
Delta Logo
9:54 a.m. - 5:26 p.m.
YYZ
-
MDW
8h 32m1 stop
Delta Logo
1:28 p.m. - 10:41 p.m.
MDW
-
YYZ
8h 13m1 stop
C$ 1,430Delta
Wed, 14 Jan - Wed, 21 Jan
Delta Logo
11:00 p.m. - 10:27 a.m.
YVR
-
MDW
9h 27m1 stop
Delta Logo
1:49 p.m. - 11:59 p.m.
MDW
-
YVR
12h 10m2 stops
C$ 1,450Delta

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 46m
  • 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 8.0.

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.
8.0
Porter AirlinesOverall score based on 401 reviews
7.0Entertainment
7.6Food
8.2Boarding
8.0Comfort
8.6Crew
Airline reviews

Much roomer than air Canada! Great flight for the price. No complaints

8.0 ExcellentDiane, Dec 2025
TPA - YYZ
Read more Porter Airlines reviews

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

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

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.

Everything you need to know for your flight to Chicago Midway Airport

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