CHI

Find First Class Flights from Boston to Chicago

1 adult
1 adult, First, 0 bags

KAYAK searches hundreds of travel sites at once for first 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 First 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 first class round-trip flight deals to Chicago

Tue, Sep 1 - Tue, Sep 29
American Airlines Logo
12:56 pm - 3:10 pm
BOS
-
ORD
3h 14mnonstop
American Airlines Logo
6:00 am - 9:39 am
ORD
-
BOS
2h 39mnonstop
$442American Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:10 am - 7:04 am
BOS
-
ORD
2h 54mnonstop
American Airlines Logo
7:29 pm - 11:06 pm
ORD
-
BOS
2h 37mnonstop
$451American Airlines
Tue, Jun 16 - Wed, Jun 17
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
$457American Airlines
Wed, Jul 8 - Tue, Jul 14
American Airlines Logo
5:10 am - 7:04 am
BOS
-
ORD
2h 54mnonstop
American Airlines Logo
11:54 am - 5:21 pm
ORD
-
BOS
4h 27m
1 stop
$483American Airlines
Fri, Jul 10 - Sun, Jul 12
American Airlines Logo
7:00 am - 11:00 am
BOS
-
ORD
5h 00m
1 stop
American Airlines Logo
6:00 am - 9:34 am
ORD
-
BOS
2h 34mnonstop
$486American Airlines
Wed, Aug 26 - Sun, Aug 30
United Airlines Logo
6:00 am - 7:59 am
BOS
-
ORD
2h 59mnonstop
United Airlines Logo
6:15 am - 9:36 am
ORD
-
BOS
2h 21mnonstop
$501United Airlines
Thu, Aug 27 - Sun, Aug 30
United Airlines Logo
8:05 am - 10:04 am
BOS
-
ORD
2h 59mnonstop
United Airlines Logo
6:15 am - 9:36 am
ORD
-
BOS
2h 21mnonstop
$505United Airlines
Tue, Jul 14 - Thu, Jul 16
Delta Logo
8:16 am - 1:09 pm
BOS
-
MDW
5h 53m
1 stop
Delta Logo
6:58 pm - 11:59 pm
MDW
-
BOS
4h 01m
1 stop
$794Delta
Fri, Aug 28 - Sun, Aug 30
Delta Logo
5:30 am - 9:17 am
BOS
-
MDW
4h 47m
1 stop
Delta Logo
6:42 pm - 11:59 pm
MDW
-
BOS
4h 17m
1 stop
$895Delta
Sun, Jun 7 - Mon, Jun 8
Delta Logo
5:30 am - 9:14 am
BOS
-
MDW
4h 44m
1 stop
Delta Logo
6:58 pm - 11:54 pm
MDW
-
BOS
3h 56m
1 stop
$897Delta

Good to Know - First Class Flights from Boston to Chicago

Low seasonJune
Average price round-trip$1,016
Good deal round-trip$864
Good deal one-way$406
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 34% increase in price.
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first 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 First 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 first 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 Friday when prices are cheapest and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Chicago, Wednesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly First 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 First Class flights from Boston to Chicago is January, where tickets cost $418 (round-trip) on average. On the other hand, the most expensive months are October and April, where the average cost of round-trip tickets is $837 and $813 respectively.

Which airlines offer First Class tickets between Boston and Chicago?

There are 3 airlines that fly First 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 $189 for a round-trip flight. On average, the best prices for flying First Class on this route can be found at United Airlines.

FAQs for First Class Boston to Chicago Flights

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

    The price of a first 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 $1,016 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 first class between Boston and Chicago?

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

KAYAK's Tips for Finding Cheap First Class Flights from Boston to Chicago

  • What’s a good price for a first class ticket between Boston and Chicago? 25% of our users found flights on this route for $272 or less one-way and $768 or less round-trip.
  • Try flying direct if you’re looking to save, as direct first class tickets are cheaper on average.

Reviews of the Top 5 Airlines Flying First 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 first 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
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
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.

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

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.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

The flight was smooth, the crew was great but the plane was quite old

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

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.

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.

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.

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

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

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.

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.