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Find Business Class Flights to Chicago

1 adult
0 bags
Fri 6/7
Fri 6/14

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
8.7Crew
7.8Entertainment
8.3Boarding
8.1Comfort
7.3Food
Airline reviews

Southwest is going downhill. I'm more apt to fly other airlines now. And I'd appreciate it if your gate agents didn't invent non-existent laws. If Southwest is having issues getting flight crews, you need to go out of your way to accommodate passengers instead of saying it's weather related and not in your hands. We can all see the other carriers are getting their planes off the ground and to/from the cities/regions you claim are weather-impacted.

8.0 ExcellentBrian, May 2024BNA - TPA
Read more about Southwest reviews

Southwest is going downhill. I'm more apt to fly other airlines now. And I'd appreciate it if your gate agents didn't invent non-existent laws. If Southwest is having issues getting flight crews, you need to go out of your way to accommodate passengers instead of saying it's weather related and not in your hands. We can all see the other carriers are getting their planes off the ground and to/from the cities/regions you claim are weather-impacted.

Southwest is a discount airline. I get it. You take the (usually) good pricing with the bad (cramped). But Southwest is becoming more and more like the cut-rate airlines *cough* Spirit *cough*. It used to actually be a fun experience. e.g. paying for WiFi is bad enough - having to pay for it on each leg of a flight is ridiculous. Yes, I've seen your numbers that it only "impacts a small percentage", but you and I both know that is misleading at best. While I used to try to fly SW exclusively when flying domestically, now I'll look elsewhere very frequently and price being equal (or close) I'm going to the other carriers.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

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).

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!

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.

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

They did a fine job. Can't wait to use Delta in the future.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Service was good for such a short flight. Small plane but smooth flight.

The flight was delayed but we got to our final destination.

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.
6/4Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
6/6Thu
nonstopAlaska Airlines
4h 44mORD-SFO
$799
6/3Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/5Wed
1 stopAlaska Airlines
7h 14mORD-SFO
$858
9/13Fri
1 stopAlaska Airlines
5h 45mSEA-ORD
9/18Wed
nonstopAlaska Airlines
4h 34mORD-SEA
$872
8/14Wed
nonstopAlaska Airlines
4h 21mSFO-ORD
8/22Thu
1 stopAlaska Airlines
7h 30mORD-SFO
$898
8/20Tue
1 stopAlaska Airlines
16h 25mSFO-ORD
8/27Tue
nonstopAlaska Airlines
4h 44mORD-SFO
$931
6/12Wed
1 stopAlaska Airlines
9h 45mSFO-ORD
7/12Fri
nonstopAlaska Airlines
4h 37mORD-SFO
$943
8/15Thu
1 stopAlaska Airlines
7h 43mSFO-ORD
8/21Wed
nonstopAlaska Airlines
4h 44mORD-SFO
$945
6/12Wed
1 stopAlaska Airlines
9h 45mSFO-ORD
6/19Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$948
8/13Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
8/22Thu
1 stopAlaska Airlines
7h 30mORD-SFO
$951
5/20Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
5/22Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$953
6/3Mon
1 stopAlaska Airlines
6h 50mSFO-ORD
6/5Wed
1 stopAlaska Airlines
7h 14mORD-SFO
$963
6/13Thu
1 stopAlaska Airlines
20h 40mSFO-ORD
6/18Tue
nonstopAlaska Airlines
4h 37mORD-SFO
$981
6/29Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
7/10Wed
1 stopAlaska Airlines
9h 47mORD-SFO
$982
6/30Sun
nonstopAlaska Airlines
4h 21mSFO-ORD
7/5Fri
1 stopAlaska Airlines
14h 53mORD-SFO
$985
7/2Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
7/5Fri
1 stopAlaska Airlines
14h 53mORD-SFO
$990
6/7Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
6/14Fri
nonstopAlaska Airlines
4h 37mORD-SFO
$992
5/20Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
5/21Tue
1 stopAlaska Airlines
8h 41mORD-SFO
$1,011
6/29Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
7/9Tue
1 stopAlaska Airlines
12h 53mORD-SFO
$1,015
5/21Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
5/23Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$1,017
6/29Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
7/5Fri
1 stopAlaska Airlines
14h 53mORD-SFO
$1,024

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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.
8/7Wed
nonstopAlaska Airlines
3h 55mSEA-ORD
$374
7/11Thu
nonstopAlaska Airlines
4h 21mSFO-ORD
$420
8/7Wed
1 stopAlaska Airlines
8h 24mSEA-ORD
$493
5/21Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$493
10/18Fri
1 stopAlaska Airlines
7h 45mSFO-ORD
$518
5/16Thu
nonstopAlaska Airlines
4h 23mSFO-ORD
$524
10/18Fri
nonstopAlaska Airlines
4h 20mSFO-ORD
$529
8/7Wed
2 stopsAlaska Airlines
10h 31mSEA-ORD
$567
6/7Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$573
7/11Thu
1 stopAlaska Airlines
20h 40mSFO-ORD
$577
10/18Fri
2 stopsAlaska Airlines
8h 45mSFO-ORD
$612
7/11Thu
2 stopsAlaska Airlines
20h 10mSFO-ORD
$618
6/11Tue
2 stopsAlaska Airlines
19h 40mLAX-ORD
$619
5/30Thu
2 stopsAlaska Airlines
19h 40mLAX-ORD
$648
6/7Fri
2 stopsAlaska Airlines
20h 40mSFO-ORD
$658
5/16Thu
1 stopAlaska Airlines
18h 00mSFO-ORD
$660
5/21Tue
2 stopsAlaska Airlines
12h 45mSFO-ORD
$668
5/15Wed
2 stopsAlaska Airlines
18h 02mLAX-ORD
$734
6/21Fri
2 stopsAlaska Airlines
15h 39mLAX-ORD
$752
8/9Fri
2 stopsAlaska Airlines
10h 26mLAX-ORD
$766

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$333
$301
$219
$38

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