$95 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 6/30. 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.
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$177
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$319
Champaign
Champaign1 stop$362
Springfield
Springfield1 stop$483
St. Louis
St. Louis2 stops$347
Decatur
Decatur1 stop$314
Paducah
Paducah1 stop$329
Chicago
Chicago1 stop$177
Moline
Moline1 stop$319
Peoria
Peoria1 stop$319
Bloomington
Bloomington1 stop$319
Champaign
Champaign1 stop$362
Springfield
Springfield1 stop$483
St. Louis
St. Louis2 stops$347
Decatur
Decatur1 stop$314
Paducah
Paducah1 stop$329

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

Thu, Aug 20 - Sun, Aug 23
JetBlue Logo
5:01 am - 8:48 am
BOS
-
ORD
4h 47m
1 stop
JetBlue Logo
6:00 am - 2:41 pm
ORD
-
BOS
7h 41m
1 stop
$177JetBlue
Wed, Jul 8 - Mon, Jul 13
Southwest Logo
5:30 pm - 7:25 pm
BOS
-
MDW
2h 55mnonstop
Southwest Logo
7:35 pm - 10:55 pm
MDW
-
BOS
2h 20mnonstop
$178Southwest
Wed, Jul 8 - Thu, Jul 9
United Airlines Logo
3:13 pm - 5:05 pm
BOS
-
ORD
2h 52mnonstop
United Airlines Logo
7:45 pm - 11:21 pm
ORD
-
BOS
2h 36mnonstop
$178United Airlines
Tue, Jul 7 - Wed, Jul 15
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
Delta Logo
6:59 am - 10:30 am
ORD
-
BOS
2h 31mnonstop
$180Delta
Mon, Aug 24 - Wed, Aug 26
United Airlines Logo
3:30 pm - 5:22 pm
BOS
-
ORD
2h 52mnonstop
United Airlines Logo
7:05 am - 12:47 pm
ORD
-
BOS
4h 42m
1 stop
$181United Airlines
Wed, Jul 22 - Fri, Jul 24
Delta Logo
7:30 am - 9:26 am
BOS
-
ORD
2h 56mnonstop
Delta Logo
7:25 pm - 11:00 pm
ORD
-
BOS
2h 35mnonstop
$183Delta
Wed, Jul 15 - Wed, Jul 22
American Airlines Logo
5:38 pm - 12:22 am
BOS
-
PIA
7h 44m
1 stop
American Airlines Logo
9:50 am - 5:36 pm
PIA
-
BOS
6h 46m
1 stop
$319American Airlines
Thu, Jul 16 - Tue, Jul 21
American Airlines Logo
5:10 am - 11:23 am
BOS
-
MLI
7h 13m
1 stop
American Airlines Logo
11:53 am - 9:33 pm
MLI
-
BOS
8h 40m
2 stops
$324American Airlines
Wed, Jul 1 - Tue, Jul 7
Frontier Logo
6:00 am - 6:51 pm
BOS
-
STL
13h 51m
2 stops
Frontier Logo
6:34 pm - 7:46 am
STL
-
BOS
12h 12m
1 stop
$348Frontier
Tue, Jul 7 - Thu, Jul 9
Frontier Logo
10:04 am - 8:57 am
BOS
-
STL
23h 53m
2 stops
Frontier Logo
6:34 pm - 7:46 am
STL
-
BOS
12h 12m
1 stop
$350Frontier
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 $197 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 $197.

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 $271 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 $371.

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 $279, 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 $169 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $301 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 25% 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$95
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 - $247 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 4239 reviews
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

4.0 OkaySteven, Jun 2026
ONT - LAS
Read more Southwest reviews

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

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

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

I have Precheck. Flew HPN to DEN and return this past weekend. Delta didn't attach my Precheck number to this trip. So it was waiting in general line especially in Denver. Unavailable.

Original flight was delayed, then cancelled and the gate staff did not expedite rebooking. Also, no instructions were given that a ticket number was needed before being called to facilitate rebooking. This could have been much more organized.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

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.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

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.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

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

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

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.

The seats were extremely cramped, with very little legroom or personal space. There was no room left in the overhead bins for a backpack, and the space under the seat in front was so limited that I could barely fit my bag underneath. Overall, the seating arrangement felt very uncomfortable and overcrowded.

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

weather delay of almost 2 hours then we landed and our gate wasn't available so we waited another 30 min

Delayed flight more than I hour. When boarding we spent some additional time on the plane before takeoff ....

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.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

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

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

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

Information on your arrival and departure airports