$67 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 2/18. 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
Chicagononstop$132
Moline
Moline1 stop$265
Peoria
Peoria1 stop$281
Bloomington
Bloomington1 stop$339
Champaign
Champaign1 stop$264
Springfield
Springfield1 stop$421
St. Louis
St. Louis1 stop$353
Decatur
Decatur1 stop$391
Paducah
Paducah1 stop$264
Chicago
Chicagononstop$132
Moline
Moline1 stop$265
Peoria
Peoria1 stop$281
Bloomington
Bloomington1 stop$339
Champaign
Champaign1 stop$264
Springfield
Springfield1 stop$421
St. Louis
St. Louis1 stop$353
Decatur
Decatur1 stop$391
Paducah
Paducah1 stop$264

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, Apr 8 - Sat, Apr 11
Southwest Logo
10:45 am - 12:25 pm
BOS
-
MDW
2h 40mnonstop
Southwest Logo
7:45 am - 11:00 am
MDW
-
BOS
2h 15mnonstop
$132Southwest
Sat, Mar 28 - Mon, Mar 30
Southwest Logo
6:35 pm - 8:30 pm
BOS
-
MDW
2h 55mnonstop
Southwest Logo
7:00 pm - 10:15 pm
MDW
-
BOS
2h 15mnonstop
$133Southwest
Mon, Feb 23 - Thu, Feb 26
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$133JetBlue
Sat, May 2 - Tue, May 5
United Airlines Logo
6:00 am - 8:00 am
BOS
-
ORD
3h 00mnonstop
United Airlines Logo
7:00 am - 12:51 pm
ORD
-
BOS
4h 51m
1 stop
$134United Airlines
Sun, Feb 22 - Thu, Feb 26
JetBlue Logo
7:00 am - 9:10 am
BOS
-
ORD
3h 10mnonstop
JetBlue Logo
10:00 am - 1:20 pm
ORD
-
BOS
2h 20mnonstop
$135JetBlue
Sat, Feb 28 - Tue, Mar 3
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
7:18 am - 10:46 am
ORD
-
BOS
2h 28mnonstop
$136American Airlines
Tue, Feb 24 - Tue, Feb 24
Delta Logo
7:15 am - 9:28 am
BOS
-
ORD
3h 13mnonstop
Delta Logo
2:25 pm - 5:51 pm
ORD
-
BOS
2h 26mnonstop
$137Delta
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
6:52 am - 9:03 am
BOS
-
ORD
3h 11mnonstop
American Airlines Logo
7:40 pm - 11:01 pm
ORD
-
BOS
2h 21mnonstop
$138American Airlines
Thu, Apr 2 - Sat, Apr 4
United Airlines Logo
5:45 am - 12:27 pm
BOS
-
MLI
7h 42m
2 stops
United Airlines Logo
6:30 am - 2:48 pm
MLI
-
BOS
7h 18m
1 stop
$284United Airlines
Thu, Jul 16 - Tue, Jul 21
Delta Logo
5:45 am - 10:26 am
BOS
-
MLI
5h 41m
1 stop
Delta Logo
11:00 am - 5:55 pm
MLI
-
BOS
5h 55m
1 stop
$289Delta
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.

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 $135 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 $135.

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 $241, 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 $187 (return) on average. On the other hand, the most expensive months are March and April, when the average cost of round-trip tickets is $256 and $256 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, Wednesday 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 38% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$67
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 2% increase in price.
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.

  • 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 $272 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $366.

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 $105 one-way - $219 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.
8.0
SouthwestOverall score based on 4280 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

2.0 MediocreDavid, Feb 2026
SAN - LAS
Read more Southwest reviews

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Was forced to check in my small carry on, even though I informed the crew it has very fragile items inside

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

No wheel chair as requested at Atlanta arrival on first flight.

Only freetext wifi was available in flight; browsing WiFi required payment. Since the seats had no in flight entertainment, Delta should revisit this policy on this longer flight.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

The flight was great as well as the airline staff

First class and monitors weren’t working for mine & my husbands. Eventually fixed, but quite annoyed as we bought first class. Also, No foot rests.

Prior to takeoff, the pilot told us there was a possibility of not being able to land and going to Portland. Well that happened, we took off and then did 8 loops around Spokane before the pilot told us we ran out of fuel and had to go to Portland. So for a 35 minute flight we have now been on the plane for 3 hours (boarded at 6:50 am and landed in Portland at 10:30). Then, we just sat in Portland's airport with no updates of when we can start heading back. All of a sudden, our pilots and crew just left, leaving us stranded in a different city and state. We continued to sit in Portland until we finally got a new crew assigned and boarded the plane (This was from 10:30-2). We then sat on the plane for an additional hour before take off because they had to count us multiple times. We finally landed in Spokane at 3:55 PM. So a flight that should have taken at max an hour took us 10 hours and we missed the majority of the recruiting event we went for.

It was delayed but other than that it was great.

Got on the plane and sat there for an hour before departure.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

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.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Enough space,crew was helpful,food was good.The gates are way far especially for travelers with health issues

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

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

Information on your arrival and departure airports