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Find First Class Flights to Chicago Midway Airport – Compare and Save

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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

Wed, 9 Sep - Sat, 12 Sep
Delta Logo
6:00 a.m. - 9:07 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:37 p.m. - 10:59 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 22m1 stop Detroit Metropolitan Wayne County
C$ 600Delta
Wed, 9 Sep - Fri, 11 Sep
Delta Logo
12:08 p.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
5h 49m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
C$ 660Delta
Wed, 9 Sep - Tue, 15 Sep
Delta Logo
9:45 a.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
8h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
C$ 660Delta
Sat, 12 Sep - Tue, 15 Sep
Delta Logo
12:08 p.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
5h 49m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
C$ 660Delta
Thu, 10 Sep - Sat, 12 Sep
Delta Logo
9:45 a.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
8h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
5:37 p.m. - 10:59 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
4h 22m1 stop Detroit Metropolitan Wayne County
C$ 688Delta
Thu, 10 Sep - Tue, 15 Sep
Delta Logo
9:45 a.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
8h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 51m1 stop Detroit Metropolitan Wayne County
C$ 746Delta
Thu, 22 Oct - Sun, 25 Oct
Delta Logo
6:00 a.m. - 9:17 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 17m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:44 p.m. - 10:56 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 12m1 stop Detroit Metropolitan Wayne County
C$ 778Delta
Wed, 23 Sep - Sun, 27 Sep
Delta Logo
6:00 a.m. - 9:07 a.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
4h 07m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 a.m. - 1:34 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 05m1 stop Detroit Metropolitan Wayne County
C$ 785Delta
Wed, 9 Sep - Sun, 13 Sep
Delta Logo
9:45 a.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
8h 12m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:40 p.m. - 10:59 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
3h 19m1 stop Detroit Metropolitan Wayne County
C$ 785Delta
Wed, 9 Sep - Mon, 14 Sep
Delta Logo
12:08 p.m. - 4:57 p.m.YYZ  Toronto Pearson Intl-MDW Chicago Midway
5h 49m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:24 a.m. - 5:20 p.m.MDW  Chicago Midway-YYZ Toronto Pearson Intl
6h 56m1 stop Detroit Metropolitan Wayne County
C$ 785Delta

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 Toronto Island Airport1h 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 and WestJet.

  • 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.

Top tips for finding first class flights to Chicago Midway Airport

  • There are no direct flights in first class between Canada and Chicago Midway Airport, so you’ll be flying with a layover.

Reviews of the top airline 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 457 reviews
6.9Entertainment
8.6Crew
7.6Food
8.2Boarding
8.0Comfort
Airline reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

10.0 ExcellentAnonymous, Aug 2026
Read more Porter Airlines reviews

A very comfortable flight, an additional wash room could have made it almost perfect.

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

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.

Organization and the adjusted times but the snacks could be of a bigger portion

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.

All good the seats a little tight and no I pad screen

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

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

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