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Find Business Class Flights to Chicago

1 adult
0 bags
Sat 6/15
Sat 6/22

Good to Know - Business Class Flights to Chicago

Low season

January

High season

August

Average price round-trip

$3,462

Good deal round-trip

$1,012

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 and Air Canada.

  • 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 6040 reviews
8.1Comfort
8.3Boarding
8.7Crew
7.8Entertainment
7.3Food
Airline reviews

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.

2.0 MediocreRubi, May 2024HOU - SAN
Read more about Southwest reviews

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.

C Am handicapped and couldn't get help with my luggage.

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!

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.

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.

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

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

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!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

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.

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.

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!!

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.
6/21Fri
nonstopAlaska Airlines
3h 55mSEA-ORD
6/25Tue
nonstopAlaska Airlines
4h 31mORD-SEA
$747
7/23Tue
1 stopAlaska Airlines
7h 30mSEA-ORD
7/28Sun
nonstopAlaska Airlines
4h 31mORD-SEA
$783
5/31Fri
1 stopAlaska Airlines
6h 55mSEA-ORD
6/4Tue
nonstopAlaska Airlines
4h 31mORD-SEA
$792
6/11Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$793
6/14Fri
nonstopAlaska Airlines
4h 04mSEA-ORD
6/21Fri
nonstopAlaska Airlines
4h 37mORD-SEA
$813
6/19Wed
nonstopAlaska Airlines
4h 06mSEA-ORD
6/19Wed
nonstopAlaska Airlines
4h 38mORD-SEA
$821
7/8Mon
nonstopAlaska Airlines
3h 59mSEA-ORD
7/12Fri
nonstopAlaska Airlines
4h 38mORD-SEA
$827
6/10Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$827
6/11Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$852
6/20Thu
nonstopAlaska Airlines
3h 55mSEA-ORD
6/21Fri
1 stopAlaska Airlines
6h 32mORD-SEA
$866
6/3Mon
nonstopAlaska Airlines
4h 23mSFO-ORD
6/5Wed
nonstopAlaska Airlines
4h 37mORD-SFO
$867
6/15Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
6/18Tue
nonstopAlaska Airlines
4h 37mORD-SFO
$868
6/6Thu
nonstopAlaska Airlines
4h 06mSEA-ORD
6/8Sat
1 stopAlaska Airlines
8h 29mORD-SEA
$871
6/17Mon
nonstopAlaska Airlines
4h 21mSFO-ORD
6/22Sat
nonstopAlaska Airlines
4h 37mORD-SFO
$892
8/26Mon
1 stopAlaska Airlines
7h 50mSFO-ORD
8/27Tue
nonstopAlaska Airlines
4h 44mORD-SFO
$898
6/15Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
6/17Mon
nonstopAlaska Airlines
4h 37mORD-SFO
$922
8/20Tue
1 stopAlaska Airlines
11h 55mSFO-ORD
8/24Sat
nonstopAlaska Airlines
4h 44mORD-SFO
$930
6/10Mon
1 stopAlaska Airlines
6h 45mSFO-ORD
6/13Thu
nonstopAlaska Airlines
4h 37mORD-SFO
$937
8/11Sun
nonstopAlaska Airlines
4h 21mSFO-ORD
8/13Tue
1 stopAlaska Airlines
10h 12mORD-SFO
$943
8/11Sun
1 stopAlaska Airlines
12h 22mSFO-ORD
8/17Sat
nonstopAlaska Airlines
4h 40mORD-SFO
$945

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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.
6/11Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$365
7/11Thu
nonstopAlaska Airlines
3h 59mSEA-ORD
$374
7/16Tue
nonstopAlaska Airlines
4h 21mSFO-ORD
$380
7/15Mon
1 stopAlaska Airlines
7h 30mSEA-ORD
$419
7/21Sun
nonstopAlaska Airlines
4h 21mSFO-ORD
$420
6/11Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
$423
5/28Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$429
6/12Wed
nonstopAlaska Airlines
4h 23mSFO-ORD
$460
5/31Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$470
6/15Sat
nonstopAlaska Airlines
4h 21mSFO-ORD
$489
7/19Fri
1 stopAlaska Airlines
8h 21mSEA-ORD
$493
5/21Tue
nonstopAlaska Airlines
4h 23mSFO-ORD
$504
10/18Fri
nonstopAlaska Airlines
4h 20mSFO-ORD
$529
10/18Fri
1 stopAlaska Airlines
19h 30mSFO-ORD
$537
6/11Tue
2 stopsAlaska Airlines
14h 00mSFO-ORD
$551
5/24Fri
nonstopAlaska Airlines
4h 23mSFO-ORD
$553
6/12Wed
2 stopsAlaska Airlines
11h 41mSFO-ORD
$571
5/21Tue
1 stopAlaska Airlines
9h 45mSFO-ORD
$572
6/15Sat
1 stopAlaska Airlines
28h 49mSFO-ORD
$577
10/18Fri
2 stopsAlaska Airlines
11h 15mSFO-ORD
$602

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$326
$296
$246
$37

Browse origins: