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Find Business Class Flights to Chicago

1 adult
0 bags
Thu 6/6
Thu 6/13

Good to Know - Business Class Flights to Chicago

Low season

January

High season

August

Average price round-trip

$3,559

Good deal round-trip

$683

Good deal one-way

$314
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 4% lower on average.
(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, Alaska 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: Alaska Airlines.

  • 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

  • To get a below average price, try to book at least 1 week in advance of your departure date.

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 the United States 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.
8.1
SouthwestOverall score based on 6075 reviews
8.1Comfort
7.3Food
8.7Crew
8.3Boarding
7.8Entertainment
Airline reviews

The flight itself was good. Delays were the problem. Original flight was scheduled for 8:10 pm. Got notifications all day -- actual time is 8:40; then 8:25; then 8:35; then 8:45. Then once I get through security, it's actually 9:35.

6.0 GoodTobin, Apr 2024PHX - BUR
Read more about Southwest reviews

The flight itself was good. Delays were the problem. Original flight was scheduled for 8:10 pm. Got notifications all day -- actual time is 8:40; then 8:25; then 8:35; then 8:45. Then once I get through security, it's actually 9:35.

Crew was great but because of fog they diverted us to Ontario instead of our Santa Barbara destination. Instead of cancelling the flight as soon as we landed in Ontario, they instead held us in Ontario for almost 4 hours before cancelling the flight. I had to rent a car in Ontario to get back to ventura on time to get an elderly relative his medication and take over his caretaking… otherwise if I had taken the buses you offered from Ontario I wouldn’t have even arrived to Santa Barbara till at least midnight (according to southwest airlines employees at Ontario), and then would have had to drive back down to ventura. At least renting the car I could get up to ventura by 10 pm to take care of my loved one.

Boarding was quick. The flight itself was good. However, no charging ports for cell phones. Also, the food provided was just a few snacks. For a 5-hr flight, I would expect at least a sandwich.

Landing was kinda fast and my ears were plugged for days after.

Healthier snack would be much appreciated. Love traveling on Southwest!

We sat on the tarmac for 2 hours waiting in line to be de-iced. The flight is 1.5 hours, so we spent more time tied to our seats for no reason than actually flying.

Best domestic airline in the USA. Excellent fares and two bags included with every fare (only carrier to do so).

Boarding was well explained and smooth. The flight was short, so there was no time for snacks. They did offer water or juice, though.

As always it was a pleasure to fly on southwest.

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

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.

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

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

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

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.

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.

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

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

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

The only issue was in the wheelchair waiting area before we got on the plane. They seemed very disorganized. Everyone we encountered after that was great! We loved Cassandra at check-in. She was awesome. The flight attendants were wonderful too! The lady helping with the waiting wheelchair when we got off the plane was awesome too!

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

I had back trouble prior to my flight and everyone was great about helping me.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Everything was good except for deplaning in NY. Took way too long!!

Jet Blue keeps getting iit wrong. 4 hour mechanical delay followed by terrible boarding experience. This is my third horrific jet blue flight in 2024. I am going to try to avoid this loser in the sky

Wish we had music during take off and landing like the last flight

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

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

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

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

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.
9/13Fri
1 stopAlaska Airlines
6h 45mSEA-ORD
9/18Wed
nonstopAlaska Airlines
4h 34mORD-SEA
$748
7/6Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
7/20Sat
nonstopAlaska Airlines
4h 37mORD-SFO
$844
8/6Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
8/12Mon
nonstopAlaska Airlines
4h 40mORD-SFO
$863
8/13Tue
1 stopAlaska Airlines
7h 20mSFO-ORD
8/22Thu
nonstopAlaska Airlines
4h 44mORD-SFO
$868
5/23Thu
1 stopAlaska Airlines
6h 55mSEA-ORD
5/29Wed
nonstopAlaska Airlines
4h 27mORD-SEA
$871
8/14Wed
nonstopAlaska Airlines
4h 21mSFO-ORD
8/22Thu
1 stopAlaska Airlines
7h 30mORD-SFO
$898
7/11Thu
nonstopAlaska Airlines
4h 21mSFO-ORD
7/14Sun
nonstopAlaska Airlines
4h 37mORD-SFO
$908
8/6Tue
1 stopAlaska Airlines
7h 20mSFO-ORD
8/12Mon
nonstopAlaska Airlines
4h 40mORD-SFO
$922
6/6Thu
nonstopAlaska Airlines
4h 23mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$943
6/20Thu
1 stopAlaska Airlines
14h 34mSFO-ORD
7/4Thu
nonstopAlaska Airlines
4h 40mORD-SFO
$950
8/13Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
8/21Wed
1 stopAlaska Airlines
7h 30mORD-SFO
$951
7/20Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
8/9Fri
1 stopAlaska Airlines
12h 53mORD-SFO
$965
7/20Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
8/8Thu
1 stopAlaska Airlines
12h 53mORD-SFO
$970
6/24Mon
nonstopAlaska Airlines
4h 21mSFO-ORD
7/15Mon
1 stopAlaska Airlines
12h 53mORD-SFO
$976
6/26Wed
nonstopAlaska Airlines
4h 21mSFO-ORD
7/17Wed
1 stopAlaska Airlines
7h 52mORD-SFO
$981
6/29Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
7/16Tue
1 stopAlaska Airlines
7h 52mORD-SFO
$982
7/21Sun
nonstopAlaska Airlines
4h 21mSFO-ORD
8/9Fri
1 stopAlaska Airlines
12h 53mORD-SFO
$985
6/6Thu
1 stopAlaska Airlines
21h 40mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$990
6/20Thu
1 stopAlaska Airlines
13h 39mSFO-ORD
7/2Tue
nonstopAlaska Airlines
4h 37mORD-SFO
$995
7/20Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
8/5Mon
1 stopAlaska Airlines
12h 53mORD-SFO
$996

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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.
5/31Fri
nonstopAlaska Airlines
4h 06mSEA-ORD
$360
5/31Fri
1 stopAlaska Airlines
8h 10mSEA-ORD
$419
7/11Thu
nonstopAlaska Airlines
4h 21mSFO-ORD
$420
6/1Sat
nonstopAlaska Airlines
4h 23mSFO-ORD
$424
5/31Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$425
6/11Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
$439
6/11Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$459
5/31Fri
1 stopAlaska Airlines
12h 45mSFO-ORD
$569
6/7Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$573
7/11Thu
1 stopAlaska Airlines
11h 15mSFO-ORD
$577
6/11Tue
2 stopsAlaska Airlines
20h 40mSFO-ORD
$588
6/4Tue
2 stopsAlaska Airlines
18h 13mLAX-ORD
$603
6/7Fri
2 stopsAlaska Airlines
20h 40mSFO-ORD
$618
6/11Tue
2 stopsAlaska Airlines
15h 12mSEA-ORD
$636
5/14Tue
2 stopsAlaska Airlines
20h 15mLAX-ORD
$644
6/18Tue
2 stopsAlaska Airlines
11h 35mLAX-ORD
$652
6/6Thu
2 stopsAlaska Airlines
18h 13mLAX-ORD
$658
6/7Fri
2 stopsAlaska Airlines
20h 40mLAX-ORD
$678
6/21Fri
2 stopsAlaska Airlines
20h 40mLAX-ORD
$752
5/16Thu
2 stopsAlaska Airlines
20h 40mSFO-ORD
$776

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$333
$301
$219
$38

Browse origins: