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Find First Class Flights to Chicago

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Sat 1/6
Sat 8/6

Good to Know - First Class Flights to Chicago

Average price round-trip

C$ 1,221

Good deal round-trip

C$ 1,144
(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 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.
8.2
WestJet EncoreOverall score based on 56 reviews
8.7Crew
7.7Comfort
7.5Food
8.6Boarding
7.6Entertainment
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"

They canceled the flight 30 minutes prior to departure without any heads up.

Like South West(2 check in baggage free) if Alaskan Airlines could give at least one check in baggage free then it would be great.

Expect to get miles for us having to miss our first planned flight due to them waiting on passengers that decided to be late to the airport.

Was not happy that we had to wait an additional 50 minutes for passengers that were still in TSA. This delay made us miss our connecting flight in Seattle to get home to tuck in our two little toddlers. We ran off the plane and ran across the entire airport trying to make this flight only to get to the gate to see that they have ended boarding. So they were willing to wait for passengers in Hawaii but not Seattle?? Especially when this wasn't even our fault. I expect to receive miles for missing our flight and spending an additional 4 hours in Seattle.

Up on arrival, due to twisted ankle, I wasn’t able to walk. Requested for a wheelchair. They immediately asked for it. After 10 minutes wait a young man named Carlos picked me up at the gate, got my baggage and took me to the pick up area. It was a great service. Thanks Alaska Air line

Once I was in my seat, it wasn't as comfortable. It was very tight (width wise).

All parts were excellent, especially staff at bag tag printing and inflight crew. Just the normal differences from past air travel could be improved but we’ve learned to accept those—cramped seats, minimal food/beverage, etc.

Delayed arrival for aircraft taking us SEA to IAD. Ground crew took way too long downloading and uploading jet for our leg so 45 minutes late. But ...aircrew saved the day flying fast to get us home on time.

Better organizing of entry and exit onto the plane regarding all of the baggage people haul on. There should be a better system so those with no baggage can get in and out more quickly. The baggage haul-on situation is absurd.

Attentive crew. Best of all was the empty seat between me and my rowmate.

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.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

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"

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

Nice smooth flight with pleasant stewards. Slept most of the flight, they could have slowly turned on the lights to make it more pleasant. Otherwise a good trip.

Great! No food was available during the flight due to the catering service strike but snacks were given throughout the flight which was nice.

Boarding, staff and flight great. A bit disappointed with no in flight online entertainment but I'll live. Landing was a bit of a jolt (more than usual) but hey everything else was smooth. LoL

I’ve been delayed for two days and I’m still stuck in Honolulu tired spending money

1.5 hours late departing YVR for a 14-minute flight. Packed waiting area. Full plane. Families with tired, screaming kids. 40-minute wait for baggage at YYJ. For a Dash-8. Obviously there was some kind of breakdown but there was no communication from anyone. Most of this was not WestJet's fault but it was an unpleasant night overall. I fell asleep in a chair waiting for the luggage carousel to start.

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

flight changed by airline. then could not check imto mew flight because kiwi had messed up the reservation. still waiting to depart…

Crew was rude.didn’t even say hi or welcome to board

I like WJ but I don’t like traveling anymore

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.
12/6Wed
directUnited Airlines
2h 43mYUL-ORD
18/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 783
8/6Sat
directUnited Airlines
2h 43mYUL-ORD
18/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 786
12/7Fri
1 stopDelta
5h 35mYYZ-MDW
17/7Wed
1 stopDelta
7h 48mMDW-YYZ
C$ 819
20/7Sat
directUnited Airlines
1h 56mYYZ-ORD
12/8Mon
directUnited Airlines
1h 43mORD-YYZ
C$ 820
31/5Fri
2 stopsDelta
14h 00mYWG-ORD
7/6Fri
2 stopsDelta
14h 59mORD-YWG
C$ 839
31/5Fri
1 stopDelta
8h 35mYWG-ORD
7/6Fri
1 stopDelta
7h 34mORD-YWG
C$ 863
13/6Thu
directUnited Airlines
2h 43mYUL-ORD
18/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 906
12/6Wed
directUnited Airlines
2h 43mYUL-ORD
17/6Mon
directUnited Airlines
2h 25mORD-YUL
C$ 907
13/6Thu
directUnited Airlines
2h 43mYUL-ORD
18/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 908
8/6Sat
directUnited Airlines
2h 43mYUL-ORD
15/6Sat
directUnited Airlines
2h 25mORD-YUL
C$ 910
9/6Sun
directUnited Airlines
2h 43mYUL-ORD
18/6Tue
directUnited Airlines
2h 23mORD-YUL
C$ 950
12/6Wed
directUnited Airlines
2h 43mYUL-ORD
20/6Thu
directUnited Airlines
2h 23mORD-YUL
C$ 959
15/5Wed
1 stopDelta
6h 13mYYZ-ORD
17/5Fri
1 stopDelta
9h 25mORD-YYZ
C$ 962
14/5Tue
directUnited Airlines
2h 45mYUL-ORD
25/5Sat
directUnited Airlines
2h 25mORD-YUL
C$ 972
18/5Sat
1 stopUnited Airlines
9h 01mYUL-ORD
19/5Sun
directUnited Airlines
2h 24mORD-YUL
C$ 1,007
12/5Sun
directUnited Airlines
2h 46mYUL-ORD
19/5Sun
directUnited Airlines
2h 24mORD-YUL
C$ 1,013
18/5Sat
1 stopUnited Airlines
9h 01mYUL-ORD
25/5Sat
directUnited Airlines
2h 25mORD-YUL
C$ 1,014
29/8Thu
2 stopsDelta
11h 03mYUL-MDW
1/9Sun
1 stopDelta
5h 34mMDW-YUL
C$ 1,053
15/5Wed
directUnited Airlines
2h 45mYUL-ORD
25/5Sat
directUnited Airlines
2h 25mORD-YUL
C$ 1,061
29/9Sun
1 stopDelta
8h 17mYYZ-ORD
13/10Sun
1 stopDelta
3h 21mORD-YYZ
C$ 1,080

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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.
14/5Tue
directUnited Airlines
2h 45mYUL-ORD
C$ 425
13/6Thu
1 stopDelta
7h 43mYUL-MDW
C$ 445
9/5Thu
1 stopDelta
6h 47mYYZ-ORD
C$ 447
9/5Thu
directUnited Airlines
2h 04mYYZ-ORD
C$ 462
12/5Sun
directUnited Airlines
2h 46mYUL-ORD
C$ 468
12/5Sun
directUnited Airlines
2h 46mYUL-ORD
C$ 471
9/5Thu
1 stopDelta
5h 36mYYZ-MDW
C$ 482
8/5Wed
1 stopDelta
7h 36mYYZ-MDW
C$ 534
10/5Fri
1 stopDelta
7h 36mYYZ-MDW
C$ 577
16/5Thu
directUnited Airlines
2h 46mYUL-ORD
C$ 614
6/6Thu
1 stopDelta
9h 42mYYC-ORD
C$ 658
28/9Sat
directDelta
3h 39mYYC-ORD
C$ 712
21/9Sat
directDelta
3h 39mYYC-ORD
C$ 714
27/8Tue
2 stopsDelta
13h 11mYVR-ORD
C$ 729
27/8Tue
1 stopDelta
8h 59mYVR-ORD
C$ 757
27/8Tue
directUnited Airlines
4h 05mYVR-ORD
C$ 768
21/5Tue
2 stopsDelta
9h 38mYWG-ORD
C$ 775
1/8Thu
2 stopsDelta
11h 13mYVR-ORD
C$ 899
22/6Sat
2 stopsDelta
8h 34mYVR-ORD
C$ 1,112
15/7Mon
directUnited Airlines
2h 28mYWG-ORD
C$ 1,166

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Flights to Chicago

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 995
C$ 834
C$ 546
C$ 281

Browse origins: