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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 9/20. 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
Mon 7/8
Mon 7/15

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Best Illinois Flight Deals

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

Chicago
Chicago1 stop$97
Moline
Moline1 stop$387
Peoria
Peoria2 stops$344
Bloomington
Bloomington1 stop$364
Champaign
Champaign1 stop$471
Springfield
Springfield1 stop$430
St. Louis
St. Louis1 stop$156

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 9% 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 10333 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

2.0 MediocreJim, Jun 2024ATL - ANC
Read more about Delta reviews

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

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

My only real complaint was how much turbulence there was-and that probably can't be avoided. I felt really sick getting off the plane. But boarding was super easy, the flight attendants were friendly, the bathroom was clean. Everything else about the flight was perfectly fine. Thanks!

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

8/24Sat
1 stopFrontier
7h 25mBOS-MDW
8/31Sat
1 stopFrontier
10h 26mMDW-BOS
$97
8/17Sat
1 stopFrontier
7h 25mBOS-MDW
8/20Tue
1 stopFrontier
10h 26mMDW-BOS
$100
6/16Sun
nonstopSpirit Airlines
2h 54mBOS-ORD
6/19Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$122
6/14Fri
nonstopSpirit Airlines
2h 54mBOS-ORD
6/19Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$123
7/2Tue
nonstopAmerican Airlines
2h 55mBOS-ORD
7/23Tue
nonstopAmerican Airlines
2h 20mORD-BOS
$138
8/7Wed
nonstopAmerican Airlines
2h 56mBOS-ORD
8/11Sun
nonstopAmerican Airlines
2h 18mORD-BOS
$157
8/22Thu
nonstopDelta
2h 59mBOS-ORD
8/26Mon
nonstopDelta
2h 26mORD-BOS
$177
6/24Mon
nonstopJetBlue
2h 54mBOS-ORD
6/24Mon
1 stopJetBlue
4h 40mORD-BOS
$196
7/5Fri
nonstopJetBlue
2h 57mBOS-ORD
7/8Mon
nonstopJetBlue
2h 26mORD-BOS
$197
6/13Thu
nonstopDelta
2h 57mBOS-ORD
6/17Mon
nonstopDelta
2h 42mORD-BOS
$210

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Recent one-way flight deals

9/20Fri
nonstopSpirit Airlines
2h 52mBOS-ORD
$29
9/5Thu
nonstopSpirit Airlines
2h 52mBOS-ORD
$30
8/17Sat
nonstopAmerican Airlines
2h 56mBOS-ORD
$69
8/17Sat
1 stopJetBlue
5h 11mBOS-ORD
$78
6/24Mon
nonstopDelta
2h 57mBOS-ORD
$79
7/4Thu
nonstopUnited Airlines
2h 48mBOS-ORD
$80
8/18Sun
nonstopAmerican Airlines
2h 53mBOS-ORD
$89
6/13Thu
1 stopJetBlue
4h 45mBOS-ORD
$91
7/9Tue
1 stopDelta
7h 19mBOS-STL
$132
6/16Sun
1 stopUnited Airlines
5h 57mBOS-STL
$138

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Last minute flights from Boston to Illinois

Last minute flight, train and bus deals

6/11Tue
multi-stopSpirit Airlines
25h 01mBOS-ORD
6/12Wed
nonstopSpirit Airlines
2h 29mORD-BOS
$85
6/13Thu
nonstopSpirit Airlines
2h 54mBOS-ORD
6/14Fri
nonstopSpirit Airlines
2h 28mORD-BOS
$109
6/13Thu
nonstopDelta
2h 57mBOS-ORD
6/17Mon
nonstopDelta
2h 42mORD-BOS
$210
6/12Wed
nonstopJetBlue
2h 54mBOS-ORD
6/18Tue
nonstopJetBlue
2h 26mORD-BOS
$250
6/12Wed
nonstopAmerican Airlines
3h 00mBOS-ORD
6/18Tue
nonstopAmerican Airlines
2h 25mORD-BOS
$251
6/12Wed
multi-stopJetBlue
5h 12mBOS-ORD
6/18Tue
nonstopJetBlue
2h 26mORD-BOS
$259
6/12Wed
multi-stopAmerican Airlines
5h 51mBOS-ORD
6/18Tue
nonstopAmerican Airlines
2h 26mORD-BOS
$260
6/12Wed
multi-stopUnited Airlines
5h 30mBOS-ORD
6/18Tue
multi-stopUnited Airlines
6h 15mORD-BOS
$265
6/11Tue
nonstopDelta
2h 57mBOS-ORD
6/13Thu
nonstopDelta
2h 28mORD-BOS
$307
6/12Wed
multi-stopUnited Airlines
5h 30mBOS-ORD
6/18Tue
multi-stopUnited Airlines
7h 16mORD-BOS
$335

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Boston - Illinois Flights