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Cheap Business Class Flight Deals to Chicago O'Hare Intl Airport

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent business class round-trip flight deals to Chicago O'Hare Intl Airport

Sun, 22 Nov - Fri, 27 Nov
American Airlines Logo
7:09 a.m. - 8:39 a.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 30mdirect
American Airlines Logo
2:50 p.m. - 5:40 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 50mdirect
C$ 620American Airlines
Sat, 21 Nov - Fri, 27 Nov
American Airlines Logo
6:21 p.m. - 7:41 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 20mdirect
American Airlines Logo
5:19 a.m. - 11:12 a.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
4h 53m1 stop Charlotte Douglas
C$ 620American Airlines
Fri, 20 Nov - Sat, 28 Nov
American Airlines Logo
6:21 p.m. - 7:41 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 20mdirect
American Airlines Logo
9:42 a.m. - 12:35 p.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 53mdirect
C$ 620American Airlines
Thu, 3 Dec - Mon, 7 Dec
United Airlines Logo
6:10 p.m. - 7:52 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl
2h 42mdirect
United Airlines Logo
7:05 a.m. - 10:17 a.m.ORD  Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl
2h 12mdirect
C$ 663United Airlines
Sat, 21 Nov - Sat, 28 Nov
Air Canada Logo
12:00 p.m. - 1:13 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 13mdirect
Air Canada Logo
8:45 a.m. - 11:27 a.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 42mdirect
C$ 845Air Canada
Sun, 14 Feb - Fri, 19 Feb
Air Canada Logo
12:00 p.m. - 1:13 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
2h 13mdirect
Air Canada Logo
8:45 a.m. - 11:28 a.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
1h 43mdirect
C$ 845Air Canada
Sat, 26 Dec - Wed, 30 Dec
United Airlines Logo
6:00 a.m. - 8:08 a.m.YUL  Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl
3h 08mdirect
United Airlines Logo
5:45 p.m. - 9:17 p.m.ORD  Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl
2h 32mdirect
C$ 912United Airlines
Fri, 18 Dec - Sun, 27 Dec
United Airlines Logo
4:45 p.m. - 6:45 p.m.YUL  Montreal Pierre Elliott Trudeau Intl-ORD Chicago O'Hare Intl
3h 00mdirect
United Airlines Logo
5:45 p.m. - 9:17 p.m.ORD  Chicago O'Hare Intl-YUL Montreal Pierre Elliott Trudeau Intl
2h 32mdirect
C$ 1,061United Airlines
Fri, 20 Nov - Sat, 28 Nov
Aeromexico Logo
10:05 a.m. - 11:39 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
14h 34m1 stop Mexico City Benito Juarez
Aeromexico Logo
8:04 a.m. - 6:20 a.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
21h 16m2 stops Atlanta Hartsfield-Jackson Mexico City Benito Juarez
C$ 6,074Aeromexico
Fri, 20 Nov - Sat, 28 Nov
Aeromexico Logo
10:05 a.m. - 11:39 p.m.YYZ  Toronto Pearson Intl-ORD Chicago O'Hare Intl
14h 34m1 stop Mexico City Benito Juarez
Aeromexico Logo
3:26 p.m. - 6:20 a.m.ORD  Chicago O'Hare Intl-YYZ Toronto Pearson Intl
13h 54m1 stop Mexico City Benito Juarez
C$ 7,270Aeromexico

Good to Know - Business Class Flights to Chicago O'Hare Intl Airport

Average price round-trip

C$ 3,283

Good deal round-trip

C$ 3,264

Good deal one-way

C$ 1,409
(avg. price over the last 2 weeks)
or less
or less

When to book business class flights to Chicago O'Hare Intl Airport

Are your dates flexible? We break down the daily and monthly prices for business class flights to Chicago O'Hare Intl Airport, so you can find the best time to fly.
Average price per month
Flight prices as travel date approaches

FAQs for Chicago O'Hare Intl Airport business class flights

  • How long is a flight to Chicago O'Hare Intl Airport?

    Flights from Seattle4h 28m
    Flights from Syracuse2h 25m
    Flights from Detroit Metropolitan Wayne County Airport1h 32m
    Flights from Québec City2h 47m
    Flights from Fargo2h 15m
  • What is the most popular airline offering Business Class flights to Chicago O'Hare Intl Airport?

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

  • How much is a Business Class ticket to Chicago O'Hare Intl Airport?

    The price of a Business Class flight ticket to Chicago varies greatly based on its origin. From Toronto, the cost generally starts at C$ 469, whereas Business Class travelers from Montreal pay around C$ 355.

  • Which airlines offer Business Class tickets on flights to Chicago O'Hare Intl Airport?

    Traveling to Chicago O'Hare Intl Airport and want to offer yourself a Business Class experience? Depending on the origin, the following airlines offer seats in Business Class: American Airlines, United Airlines and Air Canada.

  • How does KAYAK find such good deals on Business Class tickets to Chicago O'Hare Intl 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 O'Hare Intl Airport for economy class as well as Business Class travelers.

  • What is the best airline for business class flights to Chicago O'Hare Intl Airport?

    The highest-rated airline by KAYAK users offering business class flights to Chicago O'Hare Intl Airport is Porter Airlines, with an overall rating of 8.0.

Top tips for finding business class flights to Chicago O'Hare Intl Airport

  • Try flying direct if you’re looking to save money, as direct business class tickets are cheaper on average.
  • What’s a good price for a business class ticket between Canada and Chicago O'Hare Intl Airport? 25% of our users found flights on this route for C$ 1,268 or less one-way and C$ 2,291 or less round-trip.

Reviews of the top 5 airlines flying to Chicago O'Hare Intl Airport

 
Need help choosing which airline to fly business class to Chicago O'Hare Intl 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 467 reviews
8.2Boarding
7.6Food
6.9Entertainment
8.6Crew
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. :)

The Code Share with Air Canada was not very streamlined. I had to check in at airport (not online) on the outbound and return flights

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

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

Reliable, nice crew, I fly often on that flight and I like it all.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Always a pleasure to fly with WestJet. I am however frustrated about the rising costs. We have started to resort to Ultra Basic fares to afford but really missing the extra bag but too costly.

The crew were all helpful, kind, and effective. There could have been more space under the seats.

Horrible, delayed 3 hours due to a mechanical issue where the plane is deemed unsafe so we had to deplane after an hour on the tarmac. No credit was given even though plenty of passengers missed their connecting flights and then the baggage claim info showed that no flight was being loaded on the carousel whilst the bags were being dropped, so no one knew if it was the right flight or not since the arrivals screen didn’t show anything.

I'm so frustrated my flight was canceled they give flight on August 5 which is not sure. Its was big mistake I booked my ticket from kayak.

Maybe glass of wine would be nice at no charge

We traveled with a 7 year old that has autism and he is significantly cognitively delayed. Your site makes it known there are no wagons allowed even if they fold down flat and many autistic children cannot travel without one because they are unable to follow directions or cooperate with walking through the airport and are too big for a stroller. Please consider making exceptions for our special needs children. Also it would be very thoughtful if you’d allow seat selection for no fee for special needs families. The autistic child we traveled with must sit behind another adult in our family because he continuously kicks the seat in front of him and is unable to understand why that is disruptive. We had to pay quite a bit extra to have our 4 seats situated with 2 in row 19 and 2 in row 20 directly behind.

Food was not inspired but was satisfying. Same for infotainment selection. You’d think business class would come with complimentary WiFi. Crew was uniformly attentive and excellent.

Did not like the seat selection which was poor.? My daughter and I never did get seats together because it all took place at the last minute and we had to accept whatever seats were left

Very good experience. Great cabin crew. Much better than expected

crew was great, wifi was very poor could not even load a youtube video

No problems other than no seat back entertainment. Everyone was very pleasant

Snacks and drinks should be served together and air hostess was not supportive with no smile which was kind of disappointing.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

United had a delay on the flight and we lost this connection to Vancouver We lost one and half day from our time and money The reservations for the hotel and the tour was prepaid and we lost all that money 💰 So I’m very disappointed.

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

Flight was delayed because of mechanical. Could not get landing space which caused me to miss my connection. Messy and not organized.

Little bit of trouble getting my KTN and pre-check status onto the ticket, but otherwise the counter staff were friendly and truly concerned to get it right.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

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

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

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

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