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Find First Class Flights to Chicago

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Tue 4/6
Tue 11/6

Good to Know - First Class Flights to Chicago

Average price round-trip

C$ 7,763

Good deal round-trip

C$ 1,902

Good deal one-way

C$ 547
(avg. price over the last 2 weeks)
or less
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 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 Delta, with an overall rating of 8.0.

See more FAQs

Top tips for finding first class flights to Chicago

  • The most expensive day to fly First Class to Chicago is Wednesday, while the cheapest is Thursday.

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.
8.1
WestJet EncoreOverall score based on 54 reviews
7.6Comfort
7.4Food
8.6Boarding
7.5Entertainment
8.7Crew
Airline reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

10.0 ExcellentDarren, May 2023YYZ - LAX
Read more about WestJet Encore reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

Pros: "Friendly staff and the support they offered to my mother who needed a wheelchair."
Cons: "I would have liked to have had WestJet internet and entertainment access. It was not offered on our flight from Toronto to Fredericton."
Pros: "The fact that military personnel and retired military personnel and their spouse can check in luggage for free. The check in crew was also very courteous."
Pros: "It ran on time. The pilot landed the plane without a big jolt. We could board and deplane using 2 exits."
Cons: "Seat space"
Pros: "Rotten stuff cancels out the good doesn't it. Be great if you could take some courses from Stephen Covey as you are missing some skills sets in hospitality. And stop being so cheap with the 3rd rate old old movies!"
Cons: "I did not appreciate having the second row to the last on my 2nd plane coming back - I only had a turn around time of 20 minutes to catch my third Westjet flight. When we asked if the plane would wait for us - your crew just laughed in our faces."
Pros: "Great, friendly crew in this scenic trip across to Victoria. Nice new aircraft operating this route."
Pros: "Cheerfulness of WestJet employees."
Cons: "Seat comfort; seats hard. Person next to me average size but still spilled into my seat with “man-spreading” and shoulders."
Pros: "Efficient crew and reasonable seating"
Cons: "Need more legroom or a device to fold passenger legs for the flight duration..."
Pros: "Crew was good. Seats need to be updated and are confining. I appreciated being able to disembark through front and rear door."
Cons: "More space between the seats."
Pros: "the crew was very polite but the flight was too short to have a meal"
Cons: "delayed embarking"

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

The flight was excellent, I recommend people to fly with Delta

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

The crew were very welcoming and helpful. I just wish economy had a bit more leg room. My knees were constantly hitting the chair in front of me.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

Overall good flight, smooth and on time and comfortable. Disappointing that food is not served and you can't purchase the snack packs on the plane.

The space for legs in coach is better than other Airlines you can even cross your legs!!

There was a row with three women who were very loud - talking and laughing. In an open, outdoor setting that's fine. On an airplane, no. The flight attendants told the women they were the fun row. It took the woman sitting in the row ahead of the loud women to tell them they were too loud, but everyone in the general vicinity was irritated. I didn't think it would be possible to be so rowdy for so long. Then when we landed we weren't let off at a gate. We had to be bussed in and the bus contended with airline traffic. After dealing with the loud passengers, this was not what I was expecting. An incredibly disappointing experience with an airline that I have always regarded as one of the better ones.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

Comfortable seat, plenty of leg room which is so rare, overhead bin comfortably accommodated my carry-on bag. Deli box was tasty, service was good, bathrooms were clean. Uneventful flight, which I appreciate. Departed on time and landed early.

No entertainment, food was cookies & juice,water, soda or coffee.

My baggage was in another flight, anit was delayed for one hour.

The flight was delayed for 2 hrs. Because they didn’t have a crew to fly. And it is not a first time for klm to do that. Last time they cancelled my filght and rebooked me 3 days later. Not reliable airline

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

Booked connecting flights with KlM. My serving flight was the furthest part of the airport. On arrival in Zurich. My two cases arrived but only one carry on belong to my son. His three suitcase didn't arrive. After enquiring we discovered they were still in Amsterdam. We landed at 11.12. We eventually left the airport just after one.

Seats are fair enough for medium tall people. Good food all the trip. Fight attendances are warm

no issues at all... Kudos to the food. This time was really really good

The food was ok. The crew seemed like they were cranky. I had one guy get mad at me for passing in between the storage area to get to the other toilet. I can understand if it's not allowed but reprimanding me like I'm a student saying "This is the last time!" was not appropriate. During my meal time, there was a French family around me. No problems there but when we usually have meals, they are supposed to put their chair in the upright position. These people did not do it and the steward did not tell them to raise their seat in the upright position. However, I was told to do so! So, me and another person next to me had to eat with the monitor almost touching our faces. Furthermore, a lady in front of me was putting her feet up and preventing another elder passenger from putting her seat back. To make it worse, she was continuously hitting her back into her seat, shaking my monitor while I was watching a movie. A crew member did speak to her about it but then she accused me of pushing her seat forward! The crew member gave me a death stare and told me to stop pushing the seat forward. I did not even touch her seat at all, if I did, she would know it. Her boyfriend also stood up and tried to push her seat even further past the maximum decline to no avail. None of these people were reprimanded but the steward, some bald guy, was extremely friendly with them and did not even try to instruct them to do anything until it was time to land. I resisted the urge to really argue with them because I would have obviously been seen as the aggressor (I have no idea why). I hardly said anything on this flight except "more wine please" and "sorry" if I bumped into someone accidentally. Overall, it was an annoying flight and I had to resist the urge to yell at the steward and the people he was overly friendly with. The happiest moment of this flight was leaving it.

The food quality is poor. The staff are very friendly and accommodating. The entertainment program was limited. I experienced a delay of 30 minutes due to two issues. Passenger luggage had to be removed and there was a technical issue with the stairs not detaching from the aircraft. The pilot managed to compensate and we arrived only 15 minutes later. The luggage at Dubai airport was very slow. I waited over an hour.

One of their staff was so rude with discriminative. Such a reputed airline shouldn't hire such kind of arrogant attendants.

Amazing KLM service and brilliant economy comfort seats. Well worth the extra.

The boarding was one of the worst I’ve ever experienced. The fault lays on Ohare Airport and not so much the airline. The waiting area by the gate was the size to accommodate a regional flight for 20-30 people and right next to a busy walkway. When you cramped nearly 300 passengers into that space is was unbearable.

Boarding - It is unclear where the line for the group are given the signs. A solution would be a diagonal arrow pointing to the lane in which the lane for boarding of a given zone should form. As it is now, you are guessing which side of the pole the "zone 3" sign is telling you to form the line. Inflight Entertainment - The Spanish subtitles function didn't work for movie watching (in fact, all subtitles didn't work), so was difficult to follow along and I watched the movie in silence without words.

An hour-long wait to check in, 90 minutes for luggage to come out, lost luggage, chaotic operations

No everybody brings the proper equipment to enjoy the plane entertainment. Then I was not able to enjoy it.

Pros: "I like the service ,the food in thos fliggt back. Excelent"
Cons: "Better rules for people who put the seat back while we eating ,some crewmembee could say something"
Pros: "Crew friendlynesd"
Cons: "Paying a little more attention to the seating. Not everyone was socially distanced. Seat rows were unequally distributed: some were all full others were too empty."
Pros: "Seat was okay, but I thought we weren't doing center seats because of Covid risk. That plane was packed tight."
Cons: "They made me store my bag, because I had a guitar which has always been allowed as a carry on. Its a fragile instrument, and has always been allowed as a carry on."
Pros: "Seats are comfortable. Compared to other flights there is more leg room. Flight attendants where friendly."
Cons: "The flight was late on arrival, so there was more time spent in the airport. Due to this, we were right behind another flight that landed before us. Customs will only allow one plane to disembark, so we waited to get off the plan for over 30 minutes. This was the only bad experience with the trip."
Pros: "The crew was attentive."
Cons: "Check in process was super slow. It took an hour and a half. Check in process needs to be made more efficient. Also, plane took off an hour and 20 minutes later than originally planned. Therefore, we landed an hour later than expected."
Pros: "Movies and shows. Blankets. Prompt staff on plane. Snack options."
Cons: "Ticket counter was stubborn to release our boarding passes despite having already checked in online. Saying we were “too late”. The kiosk would not release our boarding passes either. Yet, we breezed right through security to the gate and we’re first to board the plane having had to actually wait awhile before boarding. The ticket counter person unnecessarily made us wait even longer when we were already running late due to having spent 11 hours in the hospital day prior from E. coli. The boarding process was also sloppy. Three different attendants asked to see our passports. Why did everyone need to verify us? We were asked very silly and seemingly unnecessary questions before boarding further slowing the process. We were asked before boarding if we had checked a bag, not sure what difference that made."
Pros: "The flight was delay about an hour, on board. The crew was great. No entertainment on board. Good complimentary bar."
Cons: "Being on time"

Book first class plane tickets to Chicago

Recent round-trip first class deals

 
We’ve provided our cheapest round-trip first class flights to Chicago found on KAYAK in the last 72 hours.
5/10Sat
directUnited Airlines
2h 05mYYZ-ORD
13/10Sun
directUnited Airlines
1h 48mORD-YYZ
C$ 744
29/8Thu
1 stopDelta
7h 24mYYZ-MDW
30/8Fri
1 stopDelta
3h 51mMDW-YYZ
C$ 792
3/6Mon
1 stopDelta
6h 08mYUL-ORD
8/6Sat
1 stopDelta
8h 00mORD-YUL
C$ 806
3/6Mon
1 stopUnited Airlines
14h 20mYYZ-ORD
10/6Mon
directUnited Airlines
1h 43mORD-YYZ
C$ 829
3/6Mon
1 stopUnited Airlines
14h 20mYYZ-ORD
10/6Mon
directUnited Airlines
1h 43mORD-YYZ
C$ 831
3/6Mon
1 stopDelta
8h 21mYUL-MDW
8/6Sat
1 stopDelta
4h 19mMDW-YUL
C$ 866
25/5Sat
1 stopUnited Airlines
9h 35mYYZ-ORD
27/5Mon
1 stopUnited Airlines
11h 01mORD-YYZ
C$ 877
24/5Fri
1 stopDelta
3h 56mYYZ-ORD
27/5Mon
1 stopDelta
3h 20mORD-YYZ
C$ 894
24/5Fri
1 stopUnited Airlines
15h 00mYYZ-ORD
27/5Mon
directUnited Airlines
1h 52mORD-YYZ
C$ 896
30/5Thu
directUnited Airlines
2h 43mYUL-ORD
8/6Sat
directUnited Airlines
2h 25mORD-YUL
C$ 911
3/6Mon
1 stopDelta
5h 13mYYZ-ORD
10/6Mon
1 stopDelta
8h 25mORD-YYZ
C$ 921
24/5Fri
1 stopDelta
5h 36mYYZ-MDW
27/5Mon
1 stopDelta
8h 25mMDW-YYZ
C$ 939
29/8Thu
directUnited Airlines
1h 56mYYZ-ORD
29/8Thu
directUnited Airlines
1h 48mORD-YYZ
C$ 944
3/6Mon
1 stopDelta
8h 01mYYZ-MDW
10/6Mon
1 stopDelta
8h 04mMDW-YYZ
C$ 958
3/6Mon
1 stopDelta
8h 01mYYZ-MDW
10/6Mon
1 stopDelta
8h 04mMDW-YYZ
C$ 959
5/10Sat
1 stopDelta
8h 17mYYZ-ORD
13/10Sun
1 stopDelta
3h 21mORD-YYZ
C$ 963
30/5Thu
directUnited Airlines
2h 43mYUL-ORD
4/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 965
2/6Sun
1 stopDelta
6h 30mYUL-MDW
7/6Fri
1 stopDelta
8h 40mMDW-YUL
C$ 996
24/8Sat
2 stopsDelta
10h 35mYUL-ORD
31/8Sat
1 stopDelta
4h 32mORD-YUL
C$ 1,018
29/9Sun
1 stopDelta
8h 17mYYZ-ORD
13/10Sun
1 stopDelta
3h 21mORD-YYZ
C$ 1,081

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Recent one-way first class deals

 
Only flying one-way? Below are some of the best deals for one-way first class flights to Chicago found on KAYAK in the last 72 hours.
16/6Sun
directUnited Airlines
2h 43mYUL-ORD
C$ 491
28/9Sat
directUnited Airlines
2h 38mYUL-ORD
C$ 624
16/6Sun
2 stopsDelta
10h 35mYYC-ORD
C$ 666
14/6Fri
directUnited Airlines
2h 25mYOW-ORD
C$ 680
28/9Sat
directDelta
3h 39mYYC-ORD
C$ 713
27/8Tue
2 stopsDelta
13h 11mYVR-ORD
C$ 721
27/8Tue
1 stopDelta
8h 59mYVR-ORD
C$ 755
27/8Tue
directUnited Airlines
4h 05mYVR-ORD
C$ 757
1/9Sun
2 stopsDelta
10h 38mYYC-ORD
C$ 770
6/10Sun
2 stopsDelta
10h 31mYUL-ORD
C$ 1,059
22/6Sat
2 stopsDelta
8h 34mYVR-ORD
C$ 1,111
22/6Sat
2 stopsDelta
8h 34mYVR-ORD
C$ 1,113

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Flights to Chicago

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 989
C$ 829
C$ 543
C$ 279

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