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Find Business Class Flights to Chicago

1 adult
0 bags
Tue 6/18
Tue 6/25

Good to Know - Business Class Flights to Chicago

Low season

January

High season

August

Average price round-trip

$3,389

Good deal round-trip

$1,145

Good deal one-way

$214
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 6027 reviews
8.3Boarding
8.1Comfort
8.7Crew
7.3Food
7.8Entertainment
Airline reviews

Left GEG had the first flight of the morning and couldn’t leave due to broken plane then got redirected on to another flight which then I missed my connecting flight so they rescheduled my connecting flight then that one took off 3 1/2 hours late my 4 1/2 hour day turned into a 12 1/2 hour day

2.0 MediocreAnonymous, May 2024GEG - LAS
Read more about Southwest reviews

Left GEG had the first flight of the morning and couldn’t leave due to broken plane then got redirected on to another flight which then I missed my connecting flight so they rescheduled my connecting flight then that one took off 3 1/2 hours late my 4 1/2 hour day turned into a 12 1/2 hour day

Easier that prior flight. The airline attendants didn’t really do most of their job as I noted in prior email.

There were 20 wheel chairs to pre- board… suggestion for those that can walk to do so, and wouldn’t loose pre- board. Prob half of them walked. Our flight was over 45 minutes late, weather related we were told… hummm. We almost missed our connection in Baltimore. My A-27 boarding placement on Baltimore flight I paid $25 for had already gotten on plane. So lost that too. No time for lunch… no service on Baltimore to Hartford flight. No one checked that seat belts fastened etc. before that flight landed… The whole thing was just very stressful. I just don’t remember a Southwest experience being that way before.

We stood on the tarmac for over an hour. Very bad turbulence the whole ride. Very to get to the restroom.

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

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!

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.

It was warm on the plane. Perhaps the people who were coughing quite often should be encouraged to wear a mask?! It was a long 4 hours.

I enjoyed the leg room at my seat, but I was in an exit row.

Why do you ask about food when only a snack is served? Actual food needs to be bought.

There was an older male crew member that was very rude to me when doing the last checks before pulling back from the terminal. There is a polite way to tell someone to put their bag under the seat. It was Mother’s Day and my mom has recently passed so it was a tough morning for me in general. There was no need to make for the snide remark “ I don’t know how many times we have said this already” as you walked away. I had held it together all morning and this interaction brought me to tears. love Alaska Airlines and this is the first time I’ve had a negative experience.

Alway a a breeze! And great mountain views on left side of plane during entire flight!

another delayed flight. no one at the desk kept us updated. we found out by an email as the desk was not even staffed up to expected takes off

They canceled my flight going back to SF after I was at the airport. Wanted me to take a flight 14 hours later. Not a happy camper.

Service was excellent. Staff at check in cleared hurdles for me so I could travel with my service animal.

Flight cancelled an hour before takeoff due to "unscheduled maintenance". New flight makes me have to wait for 5 hours in the airport, at a gate totally on the other side of where I'm at, requiring me to take a tram to get from the N terminal, to the C terminal. After waiting for 5 hours I'm informed my new flight is no longer at the gate I'm at, but instead is back in the N terminal where I was previously.

Delayed an hour and sat without updates. Ended up an hour late to destination

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.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

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.

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.

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

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.

I was seated next to someone so obese I had no space and was pushed against the window. I could not even put my tray down or work. My neck still hurts from that experience. They should not let that happen. Large people should have to pay for enough space.

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

A good set of flights but my suitcase was irreparably damaged. (Hard shell suitcase with multiple full layer cracks from one corner all the way to the zipper) I needed to rush to catch a ferry so I didn’t notice it until it was loaded into a taxi. It cost over $100 USD to replace the suitcase to travel home.

Our recent flight from edmontown to kahalui was excellent. The service staff was very friendly, knowledgeable, funny and attentive. Thanks to all involved that made or travel such a pleasant experience and we hope to fly with west jet again soon

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.
7/22Mon
nonstopAlaska Airlines
3h 55mSEA-ORD
7/30Tue
nonstopAlaska Airlines
4h 38mORD-SEA
$703
7/23Tue
1 stopAlaska Airlines
7h 30mSEA-ORD
7/31Wed
nonstopAlaska Airlines
4h 31mORD-SEA
$739
7/28Sun
nonstopAlaska Airlines
3h 55mSEA-ORD
7/31Wed
nonstopAlaska Airlines
4h 31mORD-SEA
$743
7/24Wed
nonstopAlaska Airlines
3h 55mSEA-ORD
8/2Fri
nonstopAlaska Airlines
4h 38mORD-SEA
$747
7/26Fri
1 stopAlaska Airlines
7h 30mSEA-ORD
7/30Tue
nonstopAlaska Airlines
4h 38mORD-SEA
$748
7/27Sat
nonstopAlaska Airlines
3h 55mSEA-ORD
7/28Sun
nonstopAlaska Airlines
4h 34mORD-SEA
$781
7/23Tue
1 stopAlaska Airlines
7h 30mSEA-ORD
7/28Sun
nonstopAlaska Airlines
4h 31mORD-SEA
$783
7/28Sun
nonstopAlaska Airlines
3h 55mSEA-ORD
8/3Sat
nonstopAlaska Airlines
4h 31mORD-SEA
$787
7/26Fri
1 stopAlaska Airlines
7h 30mSEA-ORD
8/2Fri
nonstopAlaska Airlines
4h 31mORD-SEA
$792
6/11Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$793
7/23Tue
1 stopAlaska Airlines
7h 30mSEA-ORD
7/30Tue
1 stopAlaska Airlines
6h 32mORD-SEA
$819
7/26Fri
nonstopAlaska Airlines
4h 04mSEA-ORD
7/26Fri
nonstopAlaska Airlines
4h 38mORD-SEA
$821
7/28Sun
nonstopAlaska Airlines
3h 55mSEA-ORD
7/30Tue
1 stopAlaska Airlines
8h 38mORD-SEA
$823
7/21Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
7/28Sun
nonstopAlaska Airlines
4h 31mORD-SEA
$827
6/10Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/14Fri
nonstopAlaska Airlines
4h 37mORD-SFO
$827
7/26Fri
1 stopAlaska Airlines
7h 30mSEA-ORD
7/30Tue
1 stopAlaska Airlines
7h 52mORD-SEA
$829
7/26Fri
1 stopAlaska Airlines
7h 30mSEA-ORD
7/29Mon
1 stopAlaska Airlines
7h 52mORD-SEA
$838
7/16Tue
1 stopAlaska Airlines
7h 43mSFO-ORD
7/20Sat
nonstopAlaska Airlines
4h 40mORD-SFO
$838
6/11Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$852
7/21Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
7/31Wed
1 stopAlaska Airlines
8h 38mORD-SEA
$863

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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.
6/10Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
$414
6/11Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$425
6/11Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
$439
6/25Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
$459
6/25Tue
1 stopAlaska Airlines
7h 43mSFO-ORD
$524
6/7Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$562
6/15Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$574
6/11Tue
2 stopsAlaska Airlines
18h 40mSFO-ORD
$593
6/15Sat
1 stopAlaska Airlines
20h 40mSFO-ORD
$597
6/6Thu
1 stopAlaska Airlines
20h 40mSFO-ORD
$657
6/7Fri
2 stopsAlaska Airlines
20h 40mSFO-ORD
$678
6/25Tue
2 stopsAlaska Airlines
21h 15mSFO-ORD
$682
5/29Wed
2 stopsAlaska Airlines
12h 22mLAX-ORD
$701
6/17Mon
2 stopsAlaska Airlines
16h 36mLAX-ORD
$723
6/6Thu
2 stopsAlaska Airlines
19h 40mSFO-ORD
$732
6/27Thu
2 stopsAlaska Airlines
16h 31mLAX-ORD
$803
8/7Wed
2 stopsAlaska Airlines
10h 09mLAX-ORD
$810
8/6Tue
2 stopsAlaska Airlines
10h 09mLAX-ORD
$830
8/1Thu
2 stopsAlaska Airlines
10h 09mLAX-ORD
$865
5/24Fri
2 stopsAlaska Airlines
21h 30mLAX-ORD
$973

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$326
$296
$246
$37

Browse origins: