CHI

Find First Class Flights to Chicago

1 adult
1 adult, First, 0 bags

KAYAK searches hundreds of travel sites at once for deals on first class flights to Chicago

 
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

 
These are the cheapest deals for flights from Canada to Chicago 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

Thu, 2 Jul - Sat, 4 Jul
Delta Logo
6:05 a.m. - 1:00 p.m.
YYZ
-
ORD
7h 55m
1 stop
Delta Logo
5:22 p.m. - 11:02 p.m.
ORD
-
YYZ
4h 40m
1 stop
C$ 679Delta
Thu, 2 Jul - Sat, 4 Jul
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 679Delta
Thu, 2 Jul - Sat, 4 Jul
Delta Logo
6:05 a.m. - 1:00 p.m.
YYZ
-
ORD
7h 55m
1 stop
Delta Logo
5:22 p.m. - 11:02 p.m.
ORD
-
YYZ
4h 40m
1 stop
C$ 680Delta
Thu, 2 Jul - Sat, 4 Jul
Delta Logo
6:05 a.m. - 9:14 a.m.
YYZ
-
MDW
4h 09m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 680Delta
Tue, 30 Jun - Fri, 3 Jul
Delta Logo
9:45 a.m. - 12:46 p.m.
YYZ
-
MDW
4h 01m
1 stop
Delta Logo
1:26 p.m. - 11:02 p.m.
MDW
-
YYZ
8h 36m
1 stop
C$ 763Delta
Sat, 1 Aug - Sat, 1 Aug
United Airlines Logo
9:45 a.m. - 11:20 a.m.
YUL
-
ORD
2h 35mdirect
United Airlines Logo
5:58 p.m. - 9:26 p.m.
ORD
-
YUL
2h 28mdirect
C$ 1,183United Airlines
Fri, 30 Oct - Mon, 2 Nov
Alaska Airlines Logo
7:00 p.m. - 1:21 p.m.
YYC
-
ORD
17h 21m
2 stops
Alaska Airlines Logo
2:07 p.m. - 8:27 p.m.
ORD
-
YYC
31h 20m
2 stops
C$ 1,762Alaska Airlines
Sun, 12 Jul - Mon, 20 Jul
Multiple Airlines Logo
11:35 p.m. - 5:40 a.m.
YVR
-
ORD
4h 05mdirect
Multiple Airlines Logo
7:45 p.m. - 10:25 p.m.
ORD
-
YVR
4h 40mdirect
C$ 1,765Multiple Airlines
Sun, 12 Jul - Mon, 20 Jul
Alaska Airlines Logo
7:55 a.m. - 6:20 a.m.
YVR
-
ORD
20h 25m
1 stop
Alaska Airlines Logo
7:20 a.m. - 11:40 a.m.
ORD
-
YVR
6h 20m
1 stop
C$ 1,869Alaska Airlines
Fri, 9 Oct - Tue, 13 Oct
United Airlines Logo
12:30 p.m. - 5:05 p.m.
YYC
-
ORD
3h 35mdirect
United Airlines Logo
8:40 a.m. - 11:28 a.m.
ORD
-
YYC
3h 48mdirect
C$ 2,024United Airlines

Good to Know - First Class Flights to Chicago

Average price round-tripC$ 1,659
Good deal round-tripC$ 1,629
(avg. price over the last 2 weeks)
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, 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 first class flights

  • What is the most popular airline offering First Class flights to Chicago?

    Among KAYAK users, United Airlines is the most popular airline offering First Class seats on flights to Chicago.

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

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

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

    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 for economy class as well as First Class travelers.

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

    The highest-rated airline by KAYAK users offering first class flights to Chicago is Porter Airlines, with an overall rating of 8.0.

Top tips for finding first class flights to Chicago

  • Look for a flight with a layover if you’re looking to save money, as direct first class flights are generally more expensive for the route.

Reviews of the top 5 airlines flying to Chicago

 
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? 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 438 reviews
8.2Boarding
7.6Food
6.9Entertainment
8.0Comfort
8.6Crew
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.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I flew from Barcelona to Chicago on UA yesterday. The flight was on time, the pilots did a great job and the flight attendants were super nice. All of them. Also food was good, and the drinks, including wine were served a few times during our flight. I highly recommend this airline.

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

The clerk at check in for my bags was very rude. My credit card was hacked during my vacation and she told me it was not possible to pay in cash for my bag. “You bought the cheapest ticket, you should have bought a ticket that included a bag. If you cannot pay with a credit card, we will not let you on this flight”. She spoke to her supervisor and then told me , I could ask other passengers, if they would use their credit card to check my bag. I had to beg 5 different people, till one agreed to use their credit card. I payed them cash of course. This was a very stressful and humiliating experience for me. I strongly suggest you build in some kind of provision for travelers who got robbed.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

I loved the fact it was on time and it was a smooth flight to my destination.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Could not make the flight. No one would help us at all

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

One crew member, Brandy was very helpful with recovering phone lost in customs. The plane was ancient and poorly maintained. Checked baggage did not arrive with flight. Almost missed flight because if insanely short layover time. Air Canada is worst flight I have ever booked with Kayak. Wanted to charge for headsets for on flight media.

The flight was good. My luggage didn’t land with me when I arrived in Columbus. So grateful I was able to get my luggage back within the 2 hours😍👍.

gave me complimentary food as the flight was not full and was attentive to my needs

It was a nice and smooth trip. Gave a friendly environment throughout the journey.

Meal and drink service was good. Old plane with old business class seats were quite disappointing

The flight was smooth, the plane was spacious and clean, the staff was kind and the food was decent.

Pretzels were a bit dry and dusty, however it is nice to have a choice between sweet and savory snacks.

Flight crew was great, and even the crew for checking bags! I had a question for a friend of mine flying tomorrow and the man I talked to was awesome and answered my questions and looked up things for me when he didn’t have to! I was able to give her current & accurate info for her flight and she was so appreciative too!!

Never flown with Air Canada before, but it's now a top choice! Loved it!

Horrible crew, horrible seats configuration, ridiculous space in the toilets, Air Canada is no longer a option.

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.