$110 Find Cheap Flights from Boston to Illinois - Compare and Save

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Cheap Flights from Boston to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Chicago
Chicagononstop$215
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington1 stop$349
Champaign
Champaign1 stop$428
Springfield
Springfield2 stops$505
Decatur
Decatur1 stop$503
Paducah
Paducah1 stop$334
Chicago
Chicagononstop$215
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington1 stop$349
Champaign
Champaign1 stop$428
Springfield
Springfield2 stops$505
Decatur
Decatur1 stop$503
Paducah
Paducah1 stop$334
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?

Flight prices are below average for this route right now.

Flights to Illinois from Boston usually cost between $232 and $398 in October.
The lowest price found in the past 5 days was $215 on JetBlue (Oct 14-Oct 17).

What is the cheapest Boston to Illinois flight route?

The cheapest ticket to Illinois from Boston found in the last 5 days was to Chicago, at $211 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 $211.

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

The cheapest time of day to fly to Illinois is generally at night, when round-trip flights cost $293 on average. Morning departures are around 2% 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 $369.

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

No, with an average price for the route of $352, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Boston to Illinois is January, when tickets cost $198 (return) on average. On the other hand, the most expensive months are October and September, when the average cost of round-trip tickets is $306 and $297 respectively.

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

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 Saturday, with Sunday being the most expensive.

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

To get a below average price on the flight from Boston to Illinois, you should book around 3 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

January

Cheapest flight

$110
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 11% 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 $170 one-way - $302 round-trip

Reviews of the top 5 airlines serving from Boston to Illinois

 
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 4215 reviews
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
Airline reviews

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

6.0 GoodMaggie, Sep 2026
Read more Southwest reviews

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

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.

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!

The cabin was definitely dated, but that's about par for the course. The flight crew were wonderful as always (always a Delta highlight), but the boarding process was slow with little direction or encouragement to get people in their seats quickly since we were already delayed.

Totally organized, quick boarding, professional staff and ON TIME! Good size seats in the cabin Wonderful experience

The flight was delayed to board, then delay in landing and extremely bumpy landing.

Could have been on time and not missed my connection

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay

The flight was delayed at the very last minute and no information, both of my round trip flights were delayed at least the BNA to Boston was informed earlier but the return one was horrible

Delayed, then set on termac before taking off for 45 minutes. After landing had to sit on termac for another 30-40 minutes. Total disaster of a flight

Stewardess was not accommodating when I requested a second drink.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Great, except the canon was so cold. Even the flight attendants put jackets on

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

The pre-order only approach for fresh food is really challenging

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

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

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.

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.

Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.

Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.

No WiFi, no power to charge phone, confusing boarding, delays

There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.

Overall, it was a fantastic experience had no movies up charge for everything haven’t flown in many many years. Crew is fantastic. Flight was good overall great experience.

Thought the economy premium experience would match that of the Amsterdam to Boston flight. Aircraft was older: chair didn’t lean back. I had to buy a blanket, which on the flight over was complimentary. Flight crew seemed disinterested all around.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

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.

Boston sucks. Everything after 4p is delayed. AA switched planes on us so we ended up being 1.5 hours late (plus the delay at Logan). Not sure why the airline says it is on time until 1 h before the flight and then it becomes a rolling delay when they knew the incoming flight was arriving after our scheduled departure time. The crew was great as were the gate agent and ground crew. Just operations that sucked.

Flight was 2 hr late but at least I was upgraded to first class

I've flown American several times this summer and I have yet to get a flight that leaves on time. However, a delay is better than a cancel. So far I have had four canceled flights and two delayed flights

The flight was delayed in 30 minute increments for a total of 4 hours and 30 minute delay. All other flights to Chicago left on time except for this one flight. If there is an issue with the inbound flight, just let customers know so they can find another flight right away, Once we got on the plane there was another 30 minute delay taking off at 10:30 at night which is very unusual that a flight wouldn't be ready to take off

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

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 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.

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…

More options for your flight from Boston to Illinois

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