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Find Business Class Flights to Chicago

1 adult
0 bags
Sat 29/6
Sat 6/7

Good to Know - Business Class Flights to Chicago

Average price round-trip

C$ 4,582

Good deal round-trip

C$ 2,020

Good deal one-way

C$ 746
(avg. price over the last 2 weeks)
or less
or less

When to book business class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for business 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 business 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 business 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 business class flights

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

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

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

    Traveling to Chicago and want to offer yourself a Business Class experience? Depending on the origin, the following airlines offer seats in Business Class: American Airlines, Air Canada and Aeromexico.

  • How does KAYAK find such good deals on Business 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 Business Class travelers.

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

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

See more FAQs

Top tips for finding business class flights to Chicago

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

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 business 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
Alaska AirlinesOverall score based on 9192 reviews
8.6Crew
8.2Boarding
7.3Entertainment
7.9Comfort
7.3Food
Airline reviews

Crew was outstanding. Flight was fine. Food was a joke! I didn't get the priority I paid for!! That pissed me off since I paid extra!!!

8.0 Excellentjim, May 2024GEG - SAN
Read more about Alaska Airlines reviews

Crew was outstanding. Flight was fine. Food was a joke! I didn't get the priority I paid for!! That pissed me off since I paid extra!!!

I liked the price of the 2 way tix. I hated having to pay $8.00 for Internet access. It should be free. Legroom and seats are very confining.

I didn’t know that food needed to be ordered ahead. Please include this in the reservation information. Overall, very good experience.

Plane hit turbulence diverted to Houston. We'll probably get in after 3am

Cabin crew very friendly and pleasant. Flight left late but we didn't know why. Alaska Airlines app was not user friendly -- app wouldn't let us upgrade our seats, but no indication if flight was full. We wound up having to call the airline to request an upgrade and we were told none was available. Waste of time. Baggage retrieval was easy.

Full flight where I had another passenger sitting in middle seat who said that he had lost 250 lbs from 500. The stewardess on exiting the flight advise me that I was going to receive a refund. I thought she was talking about another passenger. The stewardess saw that to make him comfortable I had lifted the armrest and flew for 5 hours to Seattle from Reagan DCA with a portion of his body on my seat. I survived. I flight to remember!!!!

the flight was delayed almost 3 hours and not one time was we told that it was delayed or why. I had asked one of the crew members why it was delayed, 20 minutes after the flight was supposed to take off, and was told that they had no idea what was going on and that they had not been told anything. this is FRIGHTENING!!!! No excuse!!

Given incorrect gate upon check-in, corrected by the gate attendant, D6 rather than D5, minor inconvenience. As with the previous flight, passengers were admonished to voluntarily gate-check carry-on luggage with the statement that those in the last boarding group would have no choice but to do so. If the Boeing 737 MAX8/MAX9 doesn't have room for carry-ons it's an interior design flaw on the part of Boeing. Posting an advance warning would be helpful, such as "Boeing 737 MAX planes feature limited carry-on space. Please be aware." SFO's amenities and TSA much better than MCO's. Crew was amazing! Brought my own food because Alaska's onboard selection has soy in everything. Beverage service was excellent. This was the first and last trip with Alaska after the previous flight's issues. It's no reflection on the crew of this flight. They were great.

Flights were on time. Check in was fine. Crew members were pleasant.

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

The comfort is typical of what I would expect from main cabin. I've been on flights with other airlines where the seats needed to be changed, the cushions were non-existent. So happy this was not the case. I enjoyed the movie selection. Happy pillow and blanket was provided since I forgot my own. The food was also ok. Great that we arrived early and my luggage arrived undamaged. Again in the past (not with Delta), luggage was lost or broken.

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

The 676 plane is much more comfortable in business class than the A330 and he food was a little better. I didn’t use the entertainment.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

The Priority check in in Toronto rivalled the poorest I've experienced. The young woman at the desk (7:30 AM, YYZ) was unfriendly and abrupt, behaving as though we were interrupting her day. Her inch long fingernails said it all....I really don't belong here. Other than that, WestJet personnel provided a good travel experience, especially in flight. I must say that the repeated announcements about the cabin being full and how folks should gate check their bags became tedious. WestJet should just offer free checked luggage and charge for carry on suitcases. It would save a lot of time and the voices of the gate agents.

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

The back seats are crowded and at times uncomfortable. I guess that’s part of the price of paying less for a seat.

It was okay overall, but it was a 4 hours flight and the only thing we got was snacks, I really expected breakfast.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

Keep better track of bags. Not sure how they got lost. Also not sure why it took two weeks for us to get them back. Had to buy a bunch of necessities because they were packed.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Our trip was booked to be 2 hours after arriving in Calgary but it was changed until the next morning forcing us to stay overnight in Calgary with no compensation

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Book business class plane tickets to Chicago

Recent round-trip business class deals

 
We’ve provided our cheapest round-trip business class flights to Chicago found on KAYAK in the last 72 hours.
2/10Wed
directAmerican Airlines
1h 55mYYZ-ORD
13/10Sun
directAmerican Airlines
1h 39mORD-YYZ
C$ 535
29/9Sun
directAmerican Airlines
1h 55mYYZ-ORD
13/10Sun
directAmerican Airlines
1h 39mORD-YYZ
C$ 553
29/9Sun
directAmerican Airlines
1h 55mYYZ-ORD
13/10Sun
directAmerican Airlines
1h 39mORD-YYZ
C$ 597
13/6Thu
directAmerican Airlines
1h 55mYYZ-ORD
16/6Sun
directAmerican Airlines
1h 50mORD-YYZ
C$ 608
1/7Mon
directAmerican Airlines
1h 55mYYZ-ORD
5/7Fri
directAmerican Airlines
1h 50mORD-YYZ
C$ 617
2/10Wed
1 stopAir Canada
6h 07mYYZ-ORD
13/10Sun
directAir Canada
1h 32mORD-YYZ
C$ 753
2/10Wed
1 stopAir Canada
5h 27mYYZ-ORD
13/10Sun
directAir Canada
1h 52mORD-YYZ
C$ 757
29/8Thu
1 stopAir Canada
5h 02mYUL-ORD
2/9Mon
directAir Canada
2h 23mORD-YUL
C$ 783
29/8Thu
1 stopAir Canada
4h 46mYUL-ORD
2/9Mon
directAir Canada
2h 23mORD-YUL
C$ 791
29/8Thu
1 stopAir Canada
5h 02mYUL-ORD
2/9Mon
1 stopAir Canada
6h 18mORD-YUL
C$ 865
9/7Tue
directAir Canada
2h 43mYUL-ORD
11/7Thu
directAir Canada
2h 18mORD-YUL
C$ 913
9/7Tue
1 stopAir Canada
4h 52mYUL-ORD
11/7Thu
directAir Canada
2h 18mORD-YUL
C$ 921
29/9Sun
directAir Canada
1h 53mYYZ-ORD
13/10Sun
1 stopAir Canada
5h 59mORD-YYZ
C$ 965
2/10Wed
1 stopAir Canada
6h 07mYYZ-ORD
13/10Sun
1 stopAir Canada
5h 59mORD-YYZ
C$ 969
29/9Sun
directAir Canada
1h 53mYYZ-ORD
13/10Sun
1 stopAir Canada
5h 59mORD-YYZ
C$ 982
28/6Fri
directAir Canada
2h 22mYOW-ORD
1/7Mon
directAir Canada
2h 18mORD-YOW
C$ 1,322
13/9Fri
directAir Canada
4h 11mYVR-ORD
15/9Sun
directAir Canada
4h 35mORD-YVR
C$ 1,454
13/9Fri
directMultiple Airlines
4h 11mYVR-ORD
15/9Sun
1 stopMultiple Airlines
14h 46mORD-YVR
C$ 1,471
27/6Thu
directAir Canada
4h 01mYVR-ORD
2/7Tue
1 stopAir Canada
9h 05mORD-YVR
C$ 1,829
13/9Fri
2 stopsAir Canada
12h 43mYVR-ORD
15/9Sun
2 stopsAir Canada
13h 04mORD-YVR
C$ 1,984

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Recent one-way business class deals

 
Only flying one-way? Below are some of the best deals for one-way business class flights to Chicago found on KAYAK in the last 72 hours.
10/7Wed
directAir Canada
2h 02mYYZ-ORD
C$ 402
6/10Sun
directAmerican Airlines
2h 36mYUL-ORD
C$ 415
6/10Sun
1 stopAir Canada
4h 53mYUL-ORD
C$ 441
25/8Sun
1 stopAir Canada
8h 44mYYC-ORD
C$ 583
28/9Sat
1 stopAir Canada
7h 53mYYC-ORD
C$ 664
17/6Mon
1 stopAlaska Airlines
7h 05mYVR-ORD
C$ 684
14/7Sun
directAir Canada
2h 22mYOW-ORD
C$ 698
21/6Fri
directAir Canada
4h 01mYVR-ORD
C$ 740
16/6Sun
1 stopAlaska Airlines
6h 30mYVR-ORD
C$ 822
1/8Thu
directAmerican Airlines
4h 13mYVR-ORD
C$ 844
22/6Sat
directAir Canada
4h 01mYVR-ORD
C$ 900
22/6Sat
directAir Canada
4h 01mYVR-ORD
C$ 902
21/6Fri
2 stopsAlaska Airlines
13h 45mYVR-ORD
C$ 989
16/6Sun
directAmerican Airlines
4h 13mYVR-ORD
C$ 1,091

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Flights to Chicago

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 1,010
C$ 1,089
C$ 602
C$ 265

Browse origins: