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Find cheap flights from Boston to Illinois from $29

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 9/4. 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
0 bags
Fri 7/5
Fri 7/12

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Best Illinois Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Chicago
Chicagononstop$51
Moline
Moline1 stop$425
Peoria
Peoria3 stops$366
Bloomington
Bloomington2 stops$309
Champaign
Champaign1 stop$526
Springfield
Springfield1 stop$400
Paducah
Paducah2 stops$332
St. Louis
St. Louis1 stop$159

Good to know

Low season

January

High season

May

Cheapest flight

$29
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 10% 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 to Illinois from Boston 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 to Illinois with an airline and back to Boston 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 to Illinois from Boston up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

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 $133 one-way - $241 round-trip
  • Morning departure is around 16% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.0
DeltaOverall score based on 10377 reviews
7.4Food
8.2Boarding
8.6Crew
7.9Comfort
8.0Entertainment
Airline reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

8.0 Excellentmilton, Jun 2024ANC - MSP
Read more about Delta reviews

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

They did a fine job. Can't wait to use Delta in the future.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

Mario was great. Made a night flight on a small aircraft pleasant and memorable.

Crew were exceptional. Plane was quiet and quite empty, so I had a row to sleep across.

The seat could use more support or cushion. I'm in my 50's and have back issues so the seats are a bit hard for longer flights.

The plane was in bad condition. We were taxied for mode than an hour because a light panel had feel off. The bathroom in first class had broken panels as well. Overall poor aircraft maintenance

Great, the flight attendants were very friendly and the food was also good.

The overall flight went well and the aircrew was pleasant.

Very comfortable Prem economy seats for a long haul flight. Had a problem with the tv that the crew fixed so was great!

Cathay Pacific seems to be an airline in trouble and on its way out. Lots of broken or poorly functioning things like entertainment screens, seats, and enough well trained staff to handle a full flight. Sad...

The flight crew was exceptionally good. Personal needs were well met. The food choices were very nice.

Excellent. Planes are a little older and could get some refurbishment, but besides that everything was excellent.

While I was in great pain, the seat was sufficiently comfortable to allow me to rest and not be in so much pain.

we were upgraded which was a blessing and tender mercy for us. I fell the day before and was in extreme pain from knee to shoulder. Sitting in a more comfortable seat during the flight was an unexpected blessing and experience.

Seats were very comfortable. Crew were excellent. Food very good.

Flight crew was especially thoughtful and attentive, made sure our seats were comfortable so we could rest on the long flight

Overall fine but both ways for this trip was delayed.

I had back trouble prior to my flight and everyone was great about helping me.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

Old plane. No outlets for laptop or phone. Seats worn out. Area around seat dirty.

I loved the flight and the crew. It was comfortable and smooth.

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

The seat are terrible. Don’t even think of sleeping on a Spirit flight. The kids that run the plane aka flight attendants are pretty rude and straight forward. They get the job done but without class.

I had a death in my family and booked my flight on Spirit. My flight was cancelled the morning of my flight, no explanation, no help to rebook, nobody to talk to. The next available flight was 2days later !!!! Terrible airline, will NEVER fly with them again!

They took a horrible route with a lot of turbulence and I eneded up getting sick. Even if the flight takes longer. Don't put people life at risk just to get to the airport on time.

Every thing was fine ,low price,easy on time ,clean, good staff, really no issues

Had to board plan 2x due to lack of security check after 1st boarding

Miserable. The crew was rude, the flight was delayed 5 hours for mechanical reasons and then “weather” even though other planes were leaving.

They kept Changing the flight times. It was delayed several times and at one point it was supposed to depart at 3.40am! At which point we ended up staying overnight and booked long a separate United flight for early morning departure. The spirit flight then got moved up and left at 1.30 in the morning when it was supposed to leave at 9.40pm the night before.

Flight was delayed...not horribly late. Just before push back engine shut down for a quick replacement item that took about five minutes. After that, everything was smooth and the pilot was able to make up time in the air so that our arrival time was not too far off the original anticipated arrival time.

Book cheap flights from Boston to Illinois

Recent round-trip flight deals

6/25Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
7/2Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$56
6/25Tue
nonstopSpirit Airlines
2h 54mBOS-ORD
7/2Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$57
6/18Tue
nonstopJetBlue
2h 54mBOS-ORD
6/25Tue
nonstopJetBlue
2h 26mORD-BOS
$136
7/9Tue
1 stopJetBlue
8h 38mBOS-ORD
7/17Wed
nonstopJetBlue
2h 26mORD-BOS
$146
8/16Fri
nonstopUnited Airlines
2h 45mBOS-ORD
8/18Sun
nonstopUnited Airlines
2h 22mORD-BOS
$177
8/16Fri
nonstopUnited Airlines
2h 50mBOS-ORD
8/19Mon
1 stopUnited Airlines
4h 26mORD-BOS
$187
6/16Sun
1 stopDelta
4h 55mBOS-STL
6/19Wed
1 stopDelta
6h 18mSTL-BOS
$196
6/26Wed
1 stopDelta
4h 55mBOS-STL
7/3Wed
1 stopDelta
7h 04mSTL-BOS
$279
7/31Wed
nonstopAmerican Airlines
3h 12mBOS-STL
8/3Sat
1 stopAmerican Airlines
9h 02mSTL-BOS
$297
6/26Wed
nonstopAmerican Airlines
3h 07mBOS-STL
7/3Wed
nonstopAmerican Airlines
2h 43mSTL-BOS
$311

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Recent one-way flight deals

9/4Wed
nonstopSpirit Airlines
2h 33mBOS-ORD
$29
9/6Fri
nonstopSpirit Airlines
2h 33mBOS-ORD
$30
8/24Sat
nonstopJetBlue
2h 54mBOS-ORD
$58
9/3Tue
nonstopDelta
3h 01mBOS-ORD
$69
6/18Tue
nonstopDelta
2h 57mBOS-ORD
$78
7/3Wed
nonstopUnited Airlines
2h 50mBOS-ORD
$79
6/12Wed
1 stopJetBlue
5h 12mBOS-ORD
$91
6/18Tue
1 stopUnited Airlines
5h 10mBOS-ORD
$122
6/16Sun
1 stopAmerican Airlines
5h 52mBOS-ORD
$126
6/16Sun
1 stopAmerican Airlines
5h 09mBOS-ORD
$127

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Last minute flights from Boston to Illinois

Last minute flight, train and bus deals

6/10Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$61
6/10Mon
nonstopSpirit Airlines
2h 54mBOS-ORD
6/18Tue
nonstopSpirit Airlines
2h 28mORD-BOS
$88
6/7Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
6/11Tue
nonstopAmerican Airlines
2h 25mORD-BOS
$250
6/10Mon
multi-stopJetBlue
5h 12mBOS-ORD
6/18Tue
nonstopJetBlue
2h 26mORD-BOS
$256
6/8Sat
nonstopJetBlue
2h 55mBOS-ORD
6/13Thu
multi-stopJetBlue
8h 32mORD-BOS
$259
6/9Sun
nonstopDelta
2h 57mBOS-ORD
6/16Sun
nonstopDelta
2h 28mORD-BOS
$282
6/9Sun
multi-stopDelta
5h 01mBOS-ORD
6/16Sun
nonstopDelta
2h 28mORD-BOS
$292
6/7Fri
nonstopAmerican Airlines
2h 58mBOS-ORD
6/10Mon
nonstopAmerican Airlines
2h 26mORD-BOS
$337
6/6Thu
multi-stopUnited Airlines
7h 56mBOS-STL
6/17Mon
multi-stopUnited Airlines
7h 08mSTL-BOS
$452
6/8Sat
multi-stopUnited Airlines
8h 26mBOS-STL
6/12Wed
multi-stopUnited Airlines
7h 08mSTL-BOS
$486

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Boston - Illinois Flights