CHI

Find Business Class Flights from Boston to Chicago

1 adult
1 adult, Business, 0 bags

KAYAK searches hundreds of travel sites at once for business class flights from Boston to Chicago

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

 
These are the cheapest deals for flights from Boston 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

Tue, Jun 16 - Wed, Jun 17
American Airlines Logo
7:00 am - 9:03 am
BOS
-
ORD
3h 03mnonstop
American Airlines Logo
7:00 am - 10:26 am
ORD
-
BOS
2h 26mnonstop
$389American Airlines
Tue, Jun 16 - Wed, Jun 17
American Airlines Logo
10:14 am - 3:48 pm
BOS
-
ORD
6h 34m
1 stop
American Airlines Logo
7:00 am - 10:26 am
ORD
-
BOS
2h 26mnonstop
$418American Airlines
Tue, Jun 16 - Wed, Jun 17
American Airlines Logo
7:00 am - 11:34 am
BOS
-
ORD
5h 34m
1 stop
American Airlines Logo
6:29 am - 11:46 am
ORD
-
BOS
4h 17m
1 stop
$448American Airlines
Tue, Jul 7 - Sat, Jul 11
American Airlines Logo
5:10 am - 7:04 am
BOS
-
ORD
2h 54mnonstop
American Airlines Logo
8:29 pm - 12:05 am
ORD
-
BOS
2h 36mnonstop
$455American Airlines
Fri, Jun 26 - Mon, Jun 29
American Airlines Logo
5:00 am - 6:58 am
BOS
-
ORD
2h 58mnonstop
American Airlines Logo
8:59 pm - 12:28 am
ORD
-
BOS
2h 29mnonstop
$476American Airlines
Sat, Jun 27 - Mon, Jun 29
American Airlines Logo
5:00 am - 6:58 am
BOS
-
ORD
2h 58mnonstop
American Airlines Logo
8:59 pm - 12:28 am
ORD
-
BOS
2h 29mnonstop
$494American Airlines
Fri, Jun 26 - Sun, Jun 28
American Airlines Logo
5:00 am - 6:58 am
BOS
-
ORD
2h 58mnonstop
American Airlines Logo
6:04 am - 9:30 am
ORD
-
BOS
2h 26mnonstop
$495American Airlines
Tue, Jun 16 - Wed, Jun 17
Frontier Logo
6:00 am - 11:12 am
BOS
-
MDW
6h 12m
1 stop
Frontier Logo
12:04 pm - 1:27 am
MDW
-
BOS
12h 23m
1 stop
$508Frontier
Sat, Jun 27 - Sat, Jun 27
American Airlines Logo
5:00 am - 6:58 am
BOS
-
ORD
2h 58mnonstop
American Airlines Logo
8:59 pm - 12:28 am
ORD
-
BOS
2h 29mnonstop
$513American Airlines
Tue, Jun 16 - Wed, Jun 17
Frontier Logo
9:10 am - 7:50 pm
BOS
-
ORD
11h 40m
1 stop
Frontier Logo
1:29 pm - 1:27 am
ORD
-
BOS
10h 58m
1 stop
$518Frontier

Good to Know - Business Class Flights from Boston to Chicago

Low seasonFebruary
Average price round-trip$1,274
Good deal round-trip$1,083
Good deal one-way$432
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 18% increase in price.
(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 Boston to Chicago Business Class Flights

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

What’s the cheapest day of the week to fly business class from Boston to Chicago?

The average price of all flights from Boston to Chicago clicked on KAYAK for each day over the last 12 months.

Look for departures on Monday when prices are cheapest and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly Business Class from Boston to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Boston 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 Boston to Chicago is December, where tickets cost $271 (round-trip) on average. On the other hand, the most expensive months are January and August, where the average cost of round-trip tickets is $877 and $859 respectively.

Which airlines offer Business Class tickets between Boston and Chicago?

There are 3 airlines that fly Business Class from Boston to Chicago. They are: Delta, American Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Delta at $271 for a round-trip flight. On average, the best prices for flying Business Class on this route can be found at United Airlines.

FAQs for Business Class Boston to Chicago Flights

  • How much is a business class ticket from Boston to Chicago?

    The price of a business class flight ticket between Boston 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 $1,274 for a round-trip.

  • Is it cheaper to fly business or first class between Boston and Chicago?

    Business Class tickets are usually cheaper, but that's not the case for this route, with an average return fare of $1,274, compared to $1,016 for First Class.

  • What is the best airline when flying business class between Boston 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 Boston to Chicago

  • Try flying direct if you’re looking to save, as direct business class tickets are cheaper on average.
  • What’s a good price for a business class ticket between Boston and Chicago? 25% of our users found flights on this route for $330 or less one-way and $872 or less round-trip.

Reviews of the Top 5 Airlines Flying Business Class from Boston 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 Boston 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 4264 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
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.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

Clean planes and not take my comfort class seat away.

My service light was on 15 minutes before I had to get up and find a glass of ice. And I was in business class. The meals were not for either my wife and I. She did not eat the entire 10 hour flight and I managed a bowl of soup. I was expecting much more from business with what we paid.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

My business class seat was inoperable and unable to recline for 10 hour flight.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Landed without a gate ready. Plane is extremely old and dirty.

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.

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

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Not very happy because of the long delaying which causes our luggages were not on the connection flight and nearly missed our connection flight.

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

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.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

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!

Everything you need to know for your flight to Chicago

Cabin class types available on flights from Boston to Chicago

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