$97 Find Cheap Flights from Boston to Illinois - Compare and Save

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 9/23. 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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Cheap Flights from Boston to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$175
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$319
Champaign
Champaign1 stop$306
Springfield
Springfield1 stop$515
St. Louis
St. Louis2 stops$343
Decatur
Decatur1 stop$397
Paducah
Paducah1 stop$354
Chicago
Chicagononstop$175
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$319
Champaign
Champaign1 stop$306
Springfield
Springfield1 stop$515
St. Louis
St. Louis2 stops$343
Decatur
Decatur1 stop$397
Paducah
Paducah1 stop$354

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

Sat, Aug 22 - Thu, Aug 27
Southwest Logo
8:40 am - 10:15 am
BOS
-
MDW
2h 35mnonstop
Southwest Logo
5:45 am - 9:00 am
MDW
-
BOS
2h 15mnonstop
$175Southwest
Mon, Aug 10 - Sat, Aug 15
JetBlue Logo
5:01 am - 8:52 am
BOS
-
ORD
4h 51m
1 stop
JetBlue Logo
9:40 am - 5:17 pm
ORD
-
BOS
6h 37m
1 stop
$177JetBlue
Wed, Jul 15 - Thu, Jul 16
United Airlines Logo
8:15 am - 10:12 am
BOS
-
ORD
2h 57mnonstop
United Airlines Logo
9:41 pm - 1:14 am
ORD
-
BOS
2h 33mnonstop
$178United Airlines
Thu, Jul 9 - Wed, Jul 15
United Airlines Logo
8:15 am - 10:12 am
BOS
-
ORD
2h 57mnonstop
United Airlines Logo
10:30 am - 2:07 pm
ORD
-
BOS
2h 37mnonstop
$179United Airlines
Fri, Jul 31 - Wed, Aug 5
Delta Logo
8:45 pm - 10:39 pm
BOS
-
ORD
2h 54mnonstop
Delta Logo
10:30 am - 1:59 pm
ORD
-
BOS
2h 29mnonstop
$183Delta
Wed, Jul 22 - Wed, Jul 29
American Airlines Logo
7:00 am - 11:07 am
BOS
-
CMI
5h 07m
1 stop
American Airlines Logo
11:37 am - 5:36 pm
CMI
-
BOS
4h 59m
1 stop
$306American Airlines
Wed, Jul 22 - Wed, Jul 29
American Airlines Logo
5:10 am - 11:07 am
BOS
-
CMI
6h 57m
1 stop
American Airlines Logo
6:04 am - 1:33 pm
CMI
-
BOS
6h 29m
2 stops
$312American Airlines
Wed, Jul 22 - Thu, Jul 23
Frontier Logo
11:59 am - 11:59 pm
BOS
-
STL
13h 00m
2 stops
Frontier Logo
6:34 pm - 7:46 am
STL
-
BOS
12h 12m
1 stop
$343Frontier
Wed, Jul 22 - Thu, Jul 23
Frontier Logo
11:59 am - 11:59 pm
BOS
-
STL
13h 00m
2 stops
Frontier Logo
6:34 pm - 7:46 am
STL
-
BOS
12h 12m
1 stop
$344Frontier
Fri, Sep 4 - Sat, Sep 5
Delta Logo
4:25 pm - 11:16 pm
BOS
-
BMI
7h 51m
1 stop
Delta Logo
12:09 pm - 8:27 am
BMI
-
BOS
19h 18m
2 stops
$386Delta
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 August.

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 5 days was to Chicago, at $173 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 5 days was $173.

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 3% 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 $372.

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 $276, 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 $167 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $295 and $289 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 Thursday, 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 24% 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$97
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Boston to Chicago O'Hare Airport

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 $138 one-way - $243 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 4245 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

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

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

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

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

WiFi was not working and didn’t have a beverage service

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

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

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Attendants zipped through cabin so fast hardly anyone got the water they told us we could have in the short flight. Nothing else was offered.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

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 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.

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

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Despite a bumpy flight the pilot was great. The rest of the crew on the other hand couldn’t care less if a passenger would colapse and die. Horrible service, robot like, lifeless…

Pros: "Im usually not one to sleep on ttransport but I was very comfy on this flight and was able to sleep the whole three hours"
Cons: "The snacks."

Flight left 2 hours late with no explanation as to the delay

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

My bag was not loaded on my flight. it was not communicated to me until i was waiting for my bag at my destination. there was no confirmation of when my bag was arriving and no way to track it.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

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.

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.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

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

Information on your arrival and departure airports