CHI

Find Business Class Flights from Washington, D.C. to Chicago

1 adult
1 adult, Business, 0 bags

KAYAK searches hundreds of travel sites at once for business class flights from Washington, D.C. to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Washington, D.C. to Chicago, as well as popular online travel agencies
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Cheap Business Class Flight Deals from Washington, D.C. to Chicago

 
These are the cheapest deals for flights from Washington, D.C. 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.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent business class round-trip flight deals to Chicago

Wed, Jun 24 - Thu, Jun 25
American Airlines Logo
8:00 pm - 9:32 pm
BWI
-
ORD
2h 32mnonstop
American Airlines Logo
4:18 pm - 7:28 pm
ORD
-
BWI
2h 10mnonstop
$442American Airlines
Thu, Jun 25 - Fri, Jun 26
American Airlines Logo
8:00 pm - 9:32 pm
BWI
-
ORD
2h 32mnonstop
American Airlines Logo
4:18 pm - 7:28 pm
ORD
-
BWI
2h 10mnonstop
$446American Airlines
Wed, Jun 24 - Thu, Jun 25
American Airlines Logo
8:00 pm - 9:32 pm
BWI
-
ORD
2h 32mnonstop
American Airlines Logo
6:47 pm - 12:07 am
ORD
-
BWI
4h 20m
1 stop
$451American Airlines
Wed, Jul 1 - Sat, Jul 4
Frontier Logo
8:57 pm - 8:03 am
IAD
-
ORD
12h 06m
1 stop
Frontier Logo
1:29 pm - 11:17 pm
ORD
-
IAD
8h 48m
1 stop
$512Frontier
Wed, Jul 1 - Sat, Jul 4
Frontier Logo
11:17 am - 10:11 pm
IAD
-
MDW
11h 54m
1 stop
Frontier Logo
11:59 am - 11:17 pm
MDW
-
IAD
10h 18m
1 stop
$512Frontier
Wed, Jul 1 - Sat, Jul 4
Frontier Logo
6:28 am - 11:09 am
BWI
-
MDW
5h 41m
1 stop
Frontier Logo
6:00 am - 4:26 pm
MDW
-
BWI
9h 26m
1 stop
$526Frontier
Fri, Jul 10 - Tue, Jul 14
Frontier Logo
8:33 pm - 7:53 am
IAD
-
ORD
12h 20m
1 stop
Frontier Logo
1:50 pm - 10:55 pm
ORD
-
IAD
8h 05m
1 stop
$538Frontier
Mon, Jul 20 - Wed, Jul 29
Alaska Airlines Logo
6:03 am - 6:20 am
IAD
-
ORD
25h 17m
1 stop
Alaska Airlines Logo
6:00 am - 11:59 pm
ORD
-
IAD
16h 59m
1 stop
$2,105Alaska Airlines
Mon, Jul 20 - Mon, Jul 27
Alaska Airlines Logo
6:03 am - 6:20 am
IAD
-
ORD
25h 17m
1 stop
Alaska Airlines Logo
8:20 pm - 5:11 pm
ORD
-
IAD
19h 51m
1 stop
$2,131Alaska Airlines
Mon, Jul 20 - Sun, Jul 26
Alaska Airlines Logo
6:03 am - 6:20 am
IAD
-
ORD
25h 17m
1 stop
Alaska Airlines Logo
6:00 am - 6:39 am
ORD
-
IAD
23h 39m
1 stop
$2,150Alaska Airlines

Good to Know - Business Class Flights from Washington, D.C. to Chicago

Low seasonFebruary
Average price round-trip$889
Good deal round-trip$755
Good deal one-way$444
Best time to beat the crowds with an average 45% drop in price.
Most popular time to fly and prices are also 27% 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
Flight prices as travel date approaches

KAYAK’s Insights & Trends for Washington, D.C. to Chicago Business Class Flights

Get data-powered insights and trends into flights from Washington, D.C. to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly Business Class from Washington, D.C. to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Washington, D.C. to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for Business Class flights from Washington, D.C. to Chicago is February, where tickets cost $358 (round-trip) on average. On the other hand, the most expensive months are March and October, where the average cost of round-trip tickets is $935 and $878 respectively.

Which airlines offer Business Class tickets between Washington, D.C. and Chicago?

There are 2 airlines that fly Business Class from Washington, D.C. to Chicago. They are: American Airlines and United Airlines. The cheapest price of all airlines flying this route was found with American Airlines at $361 for a round-trip flight. On average, the best prices for flying Business Class on this route can be found at American Airlines.

FAQs for Business Class Washington, D.C. to Chicago Flights

  • How much is a business class ticket from Washington, D.C. to Chicago?

    The price of a business class flight ticket between Washington, D.C. and Chicago depends on many factors, like when the ticket was booked, the departure date, season and much more. The average price for all bookings made on KAYAK for this route over the last 2 weeks is $892 for a round-trip.

  • Is it cheaper to fly business or first class between Washington, D.C. and Chicago?

    Business class tickets are usually cheaper and that is true for this route, with an average price of $892 compared to $1,105 for a round-trip flight.

  • What is the best airline when flying business class between Washington, D.C. and Chicago?

    The highest-rated airline by KAYAK users offering business class flights for this route is Southwest, with an overall rating of 7.9.

KAYAK's Tips for Finding Cheap Business Class Flights from Washington, D.C. to Chicago

  • What’s a good price for a business class ticket between Washington, D.C. and Chicago? 25% of our users found flights on this route for $476 or less one-way and $747 or less round-trip.
  • It's only possible to fly business class direct between Washington, D.C. and Chicago.

Reviews of the Top 5 Airlines Flying Business Class from Washington, D.C. 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 Washington, D.C. 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.
7.9
SouthwestOverall score based on 4265 reviews
7.0Food
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Crew was friendly and competent. Food, wine, and entertainment were excellent except the raw tuna on the flight to Split. Recommend against serving that - at least as the only option. Many medical conditions do not allow people to eat raw fish.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

On time departure and early arrival. Flight attendant very nice.

American delayed the flight for a crew rest period. The delay occurred late in the evening - the earliest i can find is 10:20 pm. With a 6 am flight anyone on the flight would have already have been asleep (unless you are insane, a vampire or on drugs) and at least for me i was already on the way to the airport at 445 am the next morning when i discovered they delayed the flight until 9 am. Given the incoming flight was in the air at 6 pm the evening before this should have been figured out a lot more timely that was there only crew to use. Just frustrating given there is no consideration for customer experience anymore in flying.

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

The captain announced to the cabin there would be a delay because they observed a "cut" on a tire during precheck that needed to be cleared by maintenance. We were delayed during this inspection and allowed to proceed after maintenance "measured the cut and decided it was acceptable". My complaint is not about the delay or due diligence. I wish the captain had been more generic when making his announcement. I was a nervous wreck all the way to Charlotte worried that we would have a blowout when landing!

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Shut down without prior notice End up with spending lots of extra $$$

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

That this is my second time the they cancel flights and they always wait until the last minute to let people know

Spirit is awful. Do not fly spirit. Nothing but delays, cancellations.

Nothing. We didn’t even have a pilot until one hour after our flight was set to depart and now we are waiting for a gate on a very hot packed aircraft. Spirit has lost its goddamn minds and we will never fly again. On the way down the delay went from 5 minutes to 6 hours to cancelled.

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Like Spirit but bad that you have to pay for water 🙃

If there are delays, it takes less than a minute for a Spirit employee to make an announcement. It’s very simple.

For a change, friendly staff at check-in and in flight.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

Everything you need to know for your flight to Chicago

Cabin class types available on flights from Washington, D.C. to Chicago

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