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Find Business Class Flights to Chicago

1 adult
0 bags
Sat 6/8
Sat 6/15

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 6072 reviews
8.7Crew
8.3Boarding
8.1Comfort
7.8Entertainment
7.3Food
Airline reviews

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.

2.0 MediocreDavid, May 2024COS - MDW
Read more about Southwest reviews

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!

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

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

Cramped older 737. Noisy passengers nearby. Wish you would change and make KC a hub with a direct from OKC. Best new airport!

The people of SW Airlines really make it nice to fly.

A bit bumpy, but otherwise uneventful, and made up some delay in flight

Seats sook to be getting smaller on the planes. Still miss the peanuts on SW but the graham crackers and brickel are better than the mix.

More assistance and clarity for travelers with gate checking and lap children

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

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.

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

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.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

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

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

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

From bag drop to boarding, it was great. In-flight is a little different. The seats were a little uncomfortable for that long of a flight. The rest of the cabin crew except for Eva was wonderful. Eva was not friendly at all. I've had to personally encounter her twice in-flight. First time was when I had to go to the lavatory in the back of the plane, and since it was the first for me to board such tiny plane, I didn't know we were using the crew toilet. She was giving me an attitude while telling me where and how to open it since it's not the regular push to open type of door. The second one was when I had to throw trash then use the lavatory again. I asked where to throw them, and unfortunately she was the only crew in the back doodling on her phone, she had to point it out to me with an attitude then told me to wait on the carpet, which I understand because I didn't realize that, but she could have been nicer. After all, I'm a paying customer, and assisting a passenger who isn't knowledgeable about the aircraft is one of the things she's there for. The rest of the experience and crew from bag drop to in-flight were excellent except for her.

It took an hour to get my bag after landing. Not exaggerating

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

We flew halfway to our destination (NYC to Burlington) and turned around due to a mechanical issue (landing gear wouldn’t retract automatically). We turned back to JFK for JetBlue’s benefit as we landed safely at JFK and could've just as easily landed safely in Burlington on our Christmas Day flight. Instead the company directed the crew to return the plane to more easily service the aircraft. The passengers landed 3 1/2 hours later and JetBlue gave each passenger $50 for the trouble. Hardly fair compensation to be separated from family on Christmas Day.

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.
6/2Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
6/12Wed
nonstopAlaska Airlines
4h 35mORD-SEA
$733
6/1Sat
nonstopAlaska Airlines
4h 04mSEA-ORD
6/14Fri
nonstopAlaska Airlines
4h 37mORD-SEA
$747
9/13Fri
1 stopAlaska Airlines
5h 45mSEA-ORD
9/18Wed
nonstopAlaska Airlines
4h 34mORD-SEA
$748
6/2Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
6/12Wed
1 stopAlaska Airlines
8h 29mORD-SEA
$769
6/7Fri
1 stopAlaska Airlines
6h 55mSEA-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SEA
$778
6/5Wed
1 stopAlaska Airlines
6h 55mSEA-ORD
6/9Sun
nonstopAlaska Airlines
4h 28mORD-SEA
$783
6/7Fri
1 stopAlaska Airlines
6h 55mSEA-ORD
6/10Mon
nonstopAlaska Airlines
4h 27mORD-SEA
$792
6/4Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
6/6Thu
nonstopAlaska Airlines
4h 44mORD-SFO
$799
6/5Wed
1 stopAlaska Airlines
6h 55mSEA-ORD
6/12Wed
1 stopAlaska Airlines
8h 29mORD-SEA
$819
6/7Fri
nonstopAlaska Airlines
4h 15mSEA-ORD
6/10Mon
nonstopAlaska Airlines
4h 27mORD-SEA
$827
6/3Mon
1 stopAlaska Airlines
6h 55mSEA-ORD
6/12Wed
1 stopAlaska Airlines
8h 29mORD-SEA
$829
6/2Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
6/13Thu
1 stopAlaska Airlines
7h 39mORD-SEA
$852
6/2Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
6/11Tue
1 stopAlaska Airlines
6h 42mORD-SEA
$857
6/3Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/5Wed
1 stopAlaska Airlines
7h 14mORD-SFO
$858
6/5Wed
1 stopAlaska Airlines
6h 55mSEA-ORD
6/11Tue
nonstopAlaska Airlines
4h 35mORD-SEA
$863
6/6Thu
nonstopAlaska Airlines
4h 06mSEA-ORD
6/13Thu
1 stopAlaska Airlines
7h 39mORD-SEA
$866
6/6Thu
nonstopAlaska Airlines
4h 06mSEA-ORD
6/11Tue
1 stopAlaska Airlines
6h 42mORD-SEA
$871
6/7Fri
1 stopAlaska Airlines
6h 55mSEA-ORD
6/11Tue
nonstopAlaska Airlines
4h 27mORD-SEA
$872
8/14Wed
nonstopAlaska Airlines
4h 21mSFO-ORD
8/22Thu
1 stopAlaska Airlines
7h 30mORD-SFO
$898
6/2Sun
nonstopAlaska Airlines
4h 06mSEA-ORD
6/10Mon
1 stopAlaska Airlines
11h 49mORD-SEA
$901

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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.
7/5Fri
nonstopAlaska Airlines
3h 55mSEA-ORD
$374
7/7Sun
nonstopAlaska Airlines
3h 55mSEA-ORD
$414
7/8Mon
1 stopAlaska Airlines
7h 30mSEA-ORD
$419
6/3Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
$420
6/17Mon
nonstopAlaska Airlines
4h 21mSFO-ORD
$432
7/10Wed
1 stopAlaska Airlines
8h 21mSEA-ORD
$493
5/21Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$493
7/5Fri
1 stopAlaska Airlines
6h 30mSEA-ORD
$498
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
6/17Mon
1 stopAlaska Airlines
14h 34mSFO-ORD
$555
5/27Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
$562
8/7Wed
2 stopsAlaska Airlines
10h 31mSEA-ORD
$567
6/9Sun
1 stopAlaska Airlines
18h 40mSFO-ORD
$569
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
5/27Mon
1 stopAlaska Airlines
18h 40mSFO-ORD
$615
6/3Mon
2 stopsAlaska Airlines
20h 40mSFO-ORD
$618

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$333
$301
$219
$38

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