$44 Find Cheap Flights from Illinois to Massachusetts

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Illinois to Massachusetts departing on 5/7. 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.
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Low season

January

High season

July

Cheapest flight

$44
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Chicago O'Hare Airport to Boston

FAQs for booking flights from Illinois to Massachusetts

  • How does KAYAK find such low prices on flights from Illinois to Massachusetts?

    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 Illinois to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Illinois to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Massachusetts 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 Illinois to Massachusetts?

    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 Illinois to Massachusetts 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 Illinois to Massachusetts?

    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 Illinois to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 5 airlines serving from Illinois to Massachusetts

Need help choosing which airline to fly with from Illinois to Massachusetts? 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 8068 reviews
8.2Boarding
7.9Entertainment
8.0Comfort
7.3Food
8.5Crew
Airline reviews

Delta is a premier airline so my expectations are most always met.

10.0 ExcellentGreg, Mar 2025PHX - MSP
Read more Delta reviews

Delta is a premier airline so my expectations are most always met.

Seats are much much more comfortable than United, which is what I usually fly

Zero updates from the pilots for 30 minutes in the tarmac

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

Had a short delay once we boarded the aircraft in Chicago, but it was fixed in no time flat then we were on our way. The pilot was able to make up the time lost and we landed 5 minute later then schedualed . Great service

Plenty of room for me and the cat in Premium Economy. Seat was comfortable. Boarding was a breeze. The lady at the special check-in desk was great, super helpful and professional.

Our seats were all the way in back of the plane,

It’s been awhile since I have traveled on United. I, along with my family who were on the flight noted how smoothly everything went . Boarding, flight crew and service was excellent.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

Love the mosaic program, being able to move to an extra space seat for free is awesome

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

I had a horrible experience from the time I dropped off my bags until the time I landed. The staff taking the bags at the check-in counter prior to security, forced me to check my baby stroller, even though it weighed less than 20 pounds. their excuse was that the wheels were too big. I have never had an issue gate checking this exact same stroller in the past either on American or on any other airline. when I asked for the agent to show me the rule about the size of the wheels on strollers, they told me to look it up on the AA website. I did so, and did not find any indication that wheel size was a problem for gate checking strollers. The only limitation would be the weight of the stroller which mine was below. I was left with a one-year-old child and all of my carry-on luggage, diaper bag, and the like to walk around the airport without the assistance of a stroller and had the same issue when I exited the plane and had to go all the way to baggage claim without a stroller. In addition, while on the airplane, I was told I can only get one bag of cookies as a snack, even though I was with a child. Apparently my child and I were supposed to share a cookie. While this latter issue is a minor one, it is just another example of the absolutely horrible customer service that American Airlines provides. In addition, the 737 aircraft that I was on was extremely hot and the air vents above the seat were so far away from the aisle and middle seats that it was comical. I could barely reach the air vent to adjust it. I had to ask the person in the window seat to do it for me. The whole experience was just a nightmare.

You were more on time than United. I'm so over united delays.

Flight was late and TSA had shut down so (almost) no passengers could get to the gate. American failed to inform TSA to stay open! Needed to get back home so we had to rent a car & drive 13 hours all through the night. It was bad.

The flight was on time and everything went very smoothly.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

I was in a wheelchair and went from international to domestic. I was transferred to several different modes of transport and expected to give a tip at each transfer. I was, although, grateful to get to the gate in time for my flight.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

WiFi could have been a little more consistent - otherwise a phenomenal and positive experience. The 1000 mile giveaway was awesome!!!

The flight took an extra 30 min to take off because we were waiting for crew to board then it took another 30 min to get off the plane because there was no parking. Just overall ridiculous also please add a head rest my neck was gonna snap off thanks.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

Helpful attendants at check-in is very good. The $70 charge for a checked bags I didn't care for.and the constant charges for picking a seat and faster check-in are too much. Please cut the prices by at least 50% would be fantastic!

Absolutely the MOST uncomfortable seat I've EVER had on ANY airline. It should be a criminal act (cruel & unusual punishment). NEVER AGAIN will I travel your airline.

The flight was delayed over an hour and we had to sit on the plane. Crew does not apologize due to the delay. Spirit will NEVER do anything to give a customer a better experience. A child next to me was kicking me the whole time. I don't ever enjoy flying with Spirit.

Easy! As long as you don’t mind no frills, our flight was enjoyable and on time

Fantastic. Had handicapped traveler and they helped us through security, helped with boarding, helped put wheelchair together, and were all very patient. A pleasant change from previous spirit flights I’ve taken. Highly recommend.

No frills, cheap price & flight was on time, I'm happy.

Flight delayed. Seat assignment doesn’t get assign until last minute. Seats don’t recline and very stiff

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

5/7Wed
1 stopSpirit Airlines
8h 30mORD-BOS
5/10Sat
1 stopSpirit Airlines
6h 53mBOS-ORD
$95
5/14Wed
1 stopSpirit Airlines
8h 30mORD-BOS
5/17Sat
1 stopSpirit Airlines
6h 53mBOS-ORD
$97
4/2Wed
nonstopAmerican Airlines
2h 23mORD-BOS
4/8Tue
nonstopAmerican Airlines
3h 10mBOS-ORD
$156
4/11Fri
nonstopUnited Airlines
2h 28mORD-BOS
4/13Sun
nonstopUnited Airlines
2h 57mBOS-ORD
$157
4/16Wed
nonstopAmerican Airlines
2h 25mORD-BOS
4/23Wed
nonstopAmerican Airlines
2h 58mBOS-ORD
$158
5/1Thu
nonstopDelta
2h 26mORD-BOS
5/6Tue
nonstopDelta
2h 56mBOS-ORD
$167
6/4Wed
1 stopJetBlue
5h 52mORD-BOS
6/11Wed
nonstopJetBlue
3h 02mBOS-ORD
$177
6/6Fri
nonstopJetBlue
2h 29mORD-BOS
6/8Sun
nonstopJetBlue
3h 01mBOS-ORD
$178
3/17Mon
nonstopUnited Airlines
2h 20mORD-BOS
3/19Wed
1 stopUnited Airlines
5h 08mBOS-ORD
$183
3/18Tue
nonstopDelta
2h 22mORD-BOS
3/21Fri
nonstopDelta
3h 00mBOS-ORD
$188

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Recent one-way flight deals

5/7Wed
1 stopSpirit Airlines
8h 30mORD-BOS
$44
5/7Wed
1 stopSpirit Airlines
10h 34mORD-BOS
$46
4/4Fri
nonstopJetBlue
2h 29mORD-BOS
$79
3/18Tue
nonstopDelta
2h 25mORD-BOS
$89
5/21Wed
1 stopJetBlue
4h 22mORD-BOS
$98
3/19Wed
1 stopDelta
6h 39mORD-ORH
$109
4/2Wed
2 stopsUnited Airlines
6h 49mSTL-BOS
$114
5/3Sat
1 stopUnited Airlines
6h 09mORD-BOS
$121
5/28Wed
1 stopAmerican Airlines
4h 24mMLI-BOS
$139
5/3Sat
nonstopAmerican Airlines
2h 14mORD-ALB
$143

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Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

3/5Wed
multi-stopSpirit Airlines
8h 27mORD-BOS
3/11Tue
multi-stopSpirit Airlines
13h 42mBOS-ORD
$176
3/5Wed
multi-stopSpirit Airlines
8h 27mORD-BOS
3/10Mon
multi-stopSpirit Airlines
28h 18mBOS-ORD
$181
3/8Sat
nonstopAmerican Airlines
2h 13mORD-BOS
3/16Sun
nonstopAmerican Airlines
3h 03mBOS-ORD
$238
3/8Sat
nonstopDelta
2h 29mORD-BOS
3/15Sat
nonstopDelta
3h 09mBOS-ORD
$242
3/8Sat
nonstopDelta
2h 29mORD-BOS
3/12Wed
nonstopDelta
3h 00mBOS-ORD
$247
3/7Fri
nonstopUnited Airlines
2h 20mORD-BOS
4/7Mon
nonstopUnited Airlines
2h 57mBOS-ORD
$252
3/8Sat
multi-stopJetBlue
6h 22mORD-BOS
3/12Wed
nonstopJetBlue
3h 00mBOS-ORD
$257
3/8Sat
multi-stopJetBlue
7h 22mORD-BOS
3/9Sun
multi-stopJetBlue
6h 39mBOS-ORD
$267
3/7Fri
nonstopAmerican Airlines
2h 22mORD-BOS
3/10Mon
nonstopAmerican Airlines
2h 58mBOS-ORD
$296
3/7Fri
nonstopUnited Airlines
2h 20mORD-BOS
3/11Tue
multi-stopUnited Airlines
5h 08mBOS-ORD
$303

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Everything you need to know for your flight to Massachusetts

Cabin class types available on flights to Illinois

Cabin classes available on flights to Illinois. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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