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Find Business Class Flights to Chicago

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Flights Deals

Cheap Business Class Flight Deals to Chicago

 
These are the cheapest deals for flights from the United States to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent business class round-trip flight deals to Chicago

KAYAK's recommended business class round-trip deals departing in the coming months from the most popular airlines that fly to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
American Airlines Logo
11:45 pm - 5:53 amLAX-ORD
4h 08mnonstop
American Airlines Logo
9:43 am - 6:06 pmORD-LAX
10h 23m1 stop
$1,033American Airlines
Find Deal
Sun, May 18 - Tue, May 20
Alaska Airlines Logo
11:32 am - 11:59 pmLAX-ORD
10h 27m2 stops
Alaska Airlines Logo
7:59 pm - 11:26 pmORD-LAX
29h 27m1 stop
$1,038Alaska Airlines
Find Deal
Thu, May 29 - Mon, Jun 9
American Airlines Logo
9:55 am - 7:38 pmLAX-ORD
7h 43m1 stop
American Airlines Logo
9:43 am - 6:06 pmORD-LAX
10h 23m1 stop
$1,043American Airlines
Find Deal
Sun, May 18 - Tue, May 20
American Airlines Logo
4:20 pm - 10:32 pmLAX-ORD
4h 12mnonstop
American Airlines Logo
10:37 pm - 1:12 amORD-LAX
4h 35mnonstop
$1,058American Airlines
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Sun, May 18 - Tue, May 20
Alaska Airlines Logo
7:00 am - 5:40 amLAX-ORD
20h 40m1 stop
Alaska Airlines Logo
6:00 am - 7:05 pmORD-LAX
15h 05m2 stops
$1,144Alaska Airlines
Find Deal
Sun, May 18 - Tue, May 20
Alaska Airlines Logo
7:00 am - 10:23 pmLAX-ORD
13h 23m2 stops
Alaska Airlines Logo
2:09 pm - 8:59 pmORD-LAX
8h 50m1 stop
$1,165Alaska Airlines
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Sun, May 25 - Thu, Jun 5
Alaska Airlines Logo
1:57 pm - 11:56 pmLAX-ORD
7h 59m1 stop
Alaska Airlines Logo
1:01 pm - 7:48 pmORD-LAX
8h 47m1 stop
$1,195Alaska Airlines
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Tue, May 20 - Thu, Sep 4
Alaska Airlines Logo
6:07 pm - 5:00 amLAX-ORD
8h 53m1 stop
Alaska Airlines Logo
7:00 am - 4:52 pmORD-LAX
11h 52m2 stops
$1,260Alaska Airlines
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Fri, Aug 22 - Mon, Aug 25
Alaska Airlines Logo
7:30 am - 10:23 pmDFW-ORD
14h 53m2 stops
Alaska Airlines Logo
6:00 am - 12:00 pmORD-DFW
30h 00m1 stop
$1,594Alaska Airlines
Find Deal
Wed, May 28 - Sun, Jun 15
Alaska Airlines Logo
5:34 pm - 11:56 pmEWR-ORD
31h 22m1 stop
Alaska Airlines Logo
7:00 am - 6:52 amORD-EWR
22h 52m2 stops
$1,880Alaska Airlines
Find Deal
Wed, May 28 - Fri, May 30
Useful Info

Good to Know - Business Class Flights to Chicago

Low seasonJanuary
High seasonJune
Average price round-trip$1,002
Good deal round-trip$583
Good deal one-way$405
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 10% 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

  • How long is a flight to Chicago?

    Flights from Dallas2h 34m
    Flights from New York2h 27m
    Flights from Denver2h 39m
    Flights from Boston2h 40m
    Flights from Miami3h 17m
  • What is the most popular airline offering Business Class flights to Chicago?

    Among KAYAK users, American 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: American Airlines and 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 Southwest, with an overall rating of 8.0.

Top tips for finding business class flights to Chicago

  • The most expensive day to fly Business Class to Chicago is Saturday, while the cheapest is Wednesday.

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.
8.0
Alaska AirlinesOverall score based on 9968 reviews
7.1Entertainment
8.5Crew
8.2Boarding
7.1Food
7.9Comfort
Airline reviews

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

6.0 GoodJulie, Apr 2025LAX - LIH
Read more Alaska Airlines reviews

Long delay before boarding. By the time I was informed of the delay I was already at the gate.

Check your emails that you sent me. 9 emails were sent telling me that my flight is Delayed. Each one with a different time 7:10, 7:55, 9:31, 9:09, 9:29, 9:44, 10:00, 9:49, and 10:10. That was how my experience went.

Personal demeanor not good on flight returning to LAX..Great and superb on the way to Portland

Even though we checked in, checked bags, and went through security, I was told at the gate that I hadn’t checked in. I was pulled aside and had to verify my identity yet again. Otherwise, the flight was fine.

Quick boarding, efficient and pleasant crew. Wish they worked the mic better in the terminal to be understood more clearly.

The app is very bugy, did not work well. Other than that it was ok.

The flight was delayed an hour and it was not disclosed to the passengers until it was time to board. There was no in-flight WiFI available and such poor communication overall. Unfortunate that I was going to miss my connecting flight with poor communication on alternatives.

Broke the wheels of my luggage. Should be more gentle with other peoples belongings. Very upset about needing a new suitcase before Christmas.

I was able to upgrade easily on the way home to first class. No problems with luggage. Efficient time management getting us to our destination on time

Interline connection was terrible. Boarding pass from American didn’t work even though it was valid. Gate agent not present to straighten out the mess until the next to the last boarding group was called.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Our bag was lost so that made unnecessary chaos On our trip

Delta is my preferred airline. I've traveled with them for years. On time in most cases, good communication, easy to use app. Most planes are pretty nice. I was on a CRJ 700/900 however, which was pretty badly aged inside and needed a refresh. No infotainment, unreliable wifi, best to download before boarding or bring a book. Food choices are really just snacks on this flight, nice variety but about what you'd expect. Great staff and prompt in departure and early arrival too. Overall quite satisfied.

Crew was friendly Love the entertainment in the seat head rest.

Delta flight was on time, seats were comfortable, and crew was nice.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The departure gate was changed from C1 to B18 but it was never announced at the C1 gate nor did I receive any email or text message or phone call about the gate change. I was in a window seat. In the other two seats next to me were Mr. Rotund and Ms. Rotunda, a youngish couple. Just the two of them should have booked three seats. I was smashed up against the wall and window for five hours. Overall, I'd say my flight sucked. Wouldn't you?

I couldn't get checked in 24 hours before either leg of my flight. I tried both my Alaska and Hawaiian codes on both apps.

We moved from the international terminal to a new location. I think there are still some bugs to work out . We didn’t receive check in notification and had to scramble to find it but i think it will work out

Not so good. The takeoff was aborted after reaching 100 knots due to a problem with the front tires. I do commend the pilot for a quick decision and preventing a potential disaster. We returned to the gate to put fresh tires on the front. Our flight was delayed for over 3 hours. The rest of the flight was okay. We were reimbursed by Hawaiian Airlines for only $50. Not too generous

Arrived at the gate with no seats assigned. Was told by gate agent the flight was full and we would not be on it. I asked the gate agent how could I be sold tickets when the flight was full. She replied, “Thats just how they do it.” I was able to get seats once I arrived at the gate. The flight itself was great. I’ll never purchase tickets without seat assignments from kayak or anyone again. Shame on kayak or Hawaiian airlines or all of you.

The pre-flight check in process was bad. The app didn't allow check-in online and forced me to check in at the airport. Alaska didn't have self-service kiosks for check in (only bag tagging stations), so I had to wait in line with people who were checking bags just to get my boarding pass.

The flight is supposed to be Hawaiian, but it's operated by Alaska. As such, I could not find my reservation on Hawaiian nor Alaska website. I could not check in on line. At the airports, even the kiosk could not find my reservation. I needed to wait in a long line to check in even though I have no bag to check. Good thing I got to the airport early enough.

The temperature on the plane was too cold and the food was not very good. Everything else was good.

Every customer service agent we came in contact with was rude, tired, overworked and indifferent

Staff was great. Heard negative things about this airline but my experience was great

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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