$117 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
Chicago1 stop$218
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington1 stop$369
Champaign
Champaign1 stop$509
Springfield
Springfield1 stop$527
Decatur
Decatur2 stops$424
Paducah
Paducah1 stop$433
Chicago
Chicago1 stop$218
Moline
Moline1 stop$349
Peoria
Peoria1 stop$349
Bloomington
Bloomington1 stop$369
Champaign
Champaign1 stop$509
Springfield
Springfield1 stop$527
Decatur
Decatur2 stops$424
Paducah
Paducah1 stop$433
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 typical for this route right now.

Flights to Illinois from Boston usually cost between $209 and $411 in November.
The lowest price found in the past 5 days was $218 on Frontier (Nov 14-Dec 2).

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 $202 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 $202.

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 $306 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 $370.

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

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $371 on average.

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 $348 and $301 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 18% 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

$117
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Boston to Chicago Midway Airport

Flights from Boston to Illinois: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Boston to Illinois 
WeiFlew with United Airlines-Oct 2026
This flight usually departs from gate B28. Enjoy a quick meal at Legal’s or Stephanie’s, refill your water bottle at the water station nearby, and enjoy the very quick boarding process implemented!
GailFlew with JetBlue-Jul 2024
Prepare for a long wait after you actually touch down. Ohare Airport is HUGE and you can taxi for a long time.

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 $188 one-way - $333 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 4217 reviews
7.4Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

2.0 MediocreKevin, Oct 2026
Read more Southwest reviews

Delayed over 3 hours, extremely rough landing on all four flights. Would not recommend

The entire crew were wonderful but 1 flight attendant stood out with his sense of humor on the microphone. I told him as much as I exited the plane.

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.

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!

Boarding was delayed by an hour and then we proceeded to sit on the tarmac for another 30-40 minutes. No clear explanation was ever given and the delay caused me to miss my connecting flight home. Was forced to stay the night in the connecting city which impacted my following workday and cause personal issues at home as well.

Good flight — left on time due to on time arrival of Pittsburgh flight

Delta keep on impressing me. Right now Delta airline is the best of them all

Good but since we got in early we had to wait on runway for our gate. That was kind of a bummer but we still got in earlier than planned For entertainment I was watching a movie and getting close to the end of it with 15 min left but it kept jumping automatically to the next movie before finishing.

13 hour delay stuck in Detroit and missed a day of meetings. It was terrible

Great crew. Comfortable seating. Nice overhead bin space. My app didn't allow me to check in for my flight to BOS. When I called Support, they didn't fix it, but just told me to check in at the airport. Seat back entertainment was great. Could be better if the audio could connect to Bluetooth.

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

⭐ Absolutely AWFUL Experience with United Airlines! If I could give United Airlines ZERO stars, I would. The seats have practically NO legroom, making the flight feel like being crammed into a tin can with nowhere to move. Comfort? Forget about it! And the fees? Absolutely ridiculous! They seem to charge you for EVERYTHING. You pay for your ticket, then get hit with extra charges for things that should be part of a decent flying experience. What’s next, charging passengers for breathing? Flying with United feels less like being a valued customer and more like being a walking wallet. The seats are uncomfortable, the legroom is pathetic, and the constant nickel-and-diming is infuriating. For the price you pay, you would think they could at least provide a little space to stretch your legs and a travel experience that doesn’t leave you feeling ripped off. Do yourself a favor and look at other airlines before booking with United. I certainly won’t be rushing to fly with them again. Absolutely disappointing from start to finish!

Flight was very smooth from Boston. But when we got to Houston, the gate was not open and we waited on the runway for over 30 min!!

My flight from Boston to SFO was fine. Crew was friendly and helpful. Food was mediocre. Fright from SFO to MNL was not as good. My flight attendant was friendly but didn’t seem to have a lot of experience. She seemed overwhelmed. Also, this was the only red eye business class flight I’ve flown which only served dinner 2 hours after takeoff in a 13 hr flight. When I woke up 1 hr before landing, everyone was eating so I assumed bkft was being served. I pushed my button for help and no one came so I approached my flight attendant and she said they don’t serve bkft but she gave me choices for lunch or dinner. I routinely fly business class but I was disappointed with the lack of service and attention I was given on this flight. Also, most airlines will offer a snack or coffee before bkft is served but this was not offered during this flight. Overall, it was disappointing.

Horrible on the chicago end. They change hates then there is a plane at the new gate so we can’t pull in. Then that plane has mechanical issue and needs to be pulled back to the gate but we can’t get to another new gate due the other plane being in the way. Horrible gate management which will cause many customers to miss connections.

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

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.

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.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

Left a bit late duee to a technical issue, but got in early

Wonderful aircraft Crew was tired,but great considering On time No complaints

Your Jet Blue representative at the check in desk in Boston on Sunday morning, October 13, was unkind and unhelpful. For that reason alone I will avoid JetBlue airlines in the future. No food or beverage on the flight due to turbulence (not your fault). However I paid extra to sit in the upgraded section in the front and did not benefit from most amenities.

Multiple delays, poor communication, dismissive staff, chaotic boarding, broken seat back entertainment. Not really much to like.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

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.

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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