$81 Find Cheap Flights from Boston to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Illinois departing on 6/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Illinois.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Illinois.
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Flight Deals

Cheap Flights from Boston to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$169
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$339
Champaign
Champaign1 stop$304
Springfield
Springfield1 stop$515
St. Louis
St. Louis1 stop$342
Decatur
Decatur2 stops$434
Paducah
Paducah1 stop$304
Chicago
Chicago1 stop$169
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$339
Champaign
Champaign1 stop$304
Springfield
Springfield1 stop$515
St. Louis
St. Louis1 stop$342
Decatur
Decatur2 stops$434
Paducah
Paducah1 stop$304

Book Cheap Boston to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Boston to Illinois that are departing in the next months. 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 round-trip flight deals from Boston to Illinois

Wed, Jun 3 - Wed, Jun 10
Frontier Logo
12:01 pm - 10:02 pm
BOS
-
MDW
11h 01m
1 stop
Frontier Logo
6:00 am - 1:27 am
MDW
-
BOS
18h 27m
1 stop
$169Frontier
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
9:12 am - 7:55 am
BOS
-
ORD
23h 43m
1 stop
Frontier Logo
6:55 am - 1:27 am
ORD
-
BOS
17h 32m
1 stop
$169Frontier
Sat, May 30 - Sun, May 31
United Airlines Logo
6:00 am - 7:58 am
BOS
-
ORD
2h 58mnonstop
United Airlines Logo
6:15 am - 9:39 am
ORD
-
BOS
2h 24mnonstop
$182United Airlines
Tue, May 26 - Thu, May 28
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
7:00 pm - 10:20 pm
MDW
-
BOS
2h 20mnonstop
$182Southwest
Sat, May 30 - Sun, May 31
Delta Logo
5:30 pm - 7:33 pm
BOS
-
ORD
3h 03mnonstop
Delta Logo
7:00 am - 10:35 am
ORD
-
BOS
2h 35mnonstop
$183Delta
Sat, May 30 - Sun, May 31
American Airlines Logo
5:05 am - 7:02 am
BOS
-
ORD
2h 57mnonstop
American Airlines Logo
6:00 am - 9:27 am
ORD
-
BOS
2h 27mnonstop
$184American Airlines
Sat, May 30 - Mon, Jun 1
American Airlines Logo
6:41 pm - 9:05 pm
BOS
-
ORD
3h 24mnonstop
American Airlines Logo
8:45 pm - 12:15 am
ORD
-
BOS
2h 30mnonstop
$186American Airlines
Wed, Jun 3 - Tue, Jun 9
Southwest Logo
7:20 am - 9:05 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
9:00 am - 12:15 pm
MDW
-
BOS
2h 15mnonstop
$187Southwest
Sun, Nov 8 - Sat, Nov 14
United Airlines Logo
6:00 am - 12:50 pm
BOS
-
CMI
7h 50m
1 stop
United Airlines Logo
6:30 am - 12:47 pm
CMI
-
BOS
5h 17m
1 stop
$304United Airlines
Tue, Aug 4 - Fri, Aug 14
Delta Logo
5:30 am - 10:25 am
BOS
-
MLI
5h 55m
1 stop
Delta Logo
5:09 pm - 11:41 pm
MLI
-
BOS
5h 32m
1 stop
$347Delta
Booking Insights

KAYAK's insights & trends for Boston to Illinois flights

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

How much is a round-trip flight from Boston to Illinois?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Boston to Illinois departing in June.

What is the cheapest Boston to Illinois flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Boston found in the last 72 hours was to Chicago, at $168 round-trip. The most popular route is from Boston (BOS) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $168.

What is the cheapest time of day to fly to Illinois?

The average price for all round-trip flights from Boston to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $270 on average. Morning departures are around 4% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $364.

Can I save money by flying with a layover from Boston to Illinois?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $270, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Boston to Illinois?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Illinois, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Boston to Illinois is September, when tickets cost $166 (return) on average. On the other hand, the most expensive months are April and August, when the average cost of round-trip tickets is $295 and $283 respectively.

What’s the cheapest day of the week to fly from Boston to Illinois?

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

For Boston to Illinois, Friday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Illinois back to Boston, the best deals are generally found on Wednesday, with Monday being the most expensive.

How far in advance should I book a flight from Boston to Illinois?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Boston to Illinois, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Boston to Illinois, you should book around 2 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$81
Best time to beat the crowds but there is an average 15% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Boston to St. Louis

FAQs - booking Illinois flights

  • How does KAYAK find such low prices on flights from Boston to Illinois?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Boston to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Boston to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Boston to Illinois?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Boston to Illinois with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Boston to Illinois?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Boston to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Boston to the following destinations at these prices or less: Chicago $130 one-way - $233 round-trip

Reviews of the top 5 airlines serving from Boston to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Boston to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Boston to Illinois? 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 4297 reviews
8.6Crew
8.1Boarding
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

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

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

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.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

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

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

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.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

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.

Boarding was quick and efficient. We arrived at our destination early.

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.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

The staff are very, very professional. It's what flying should feel like.

Everything you need to know for your flight from Boston to Illinois

Information on your arrival and departure airports