$50 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 4/15. 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

Search hundreds of travel sites at once for deals on flights to Massachusetts

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Good to know

Low season

January

High season

July

Cheapest flight

$50
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 26% lower on average.
Flight from Chicago Midway 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 8507 reviews
8.6Crew
8.2Boarding
7.3Food
7.9Entertainment
8.0Comfort
Airline reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

10.0 ExcellentD, Jan 2025ABE - ATL
Read more Delta reviews

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

I think they can provide the better food/snack option for the 4 hours flight. Drinks are fine.

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.

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.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

I was forced to check my carry-on backpack despite there being space - but it came out on the baggage carousel so fast it didn't even delay my pickup. Otherwise a good flight. Boarding began early (which was disadvantageous for me) but fine.

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

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

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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

The flight was delayed, and we waited for more than an hour on the plane.

Could at least have little recline in economy seats and windows to the last row, they were super uncomfortable and lots of chit chat and disturbance from the operation of crew members and other passengers

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

2/4Tue
1 stopFrontier
8h 40mORD-BOS
2/5Wed
1 stopFrontier
7h 45mBOS-ORD
$109
2/10Mon
1 stopFrontier
11h 54mMDW-BOS
2/11Tue
1 stopFrontier
11h 16mBOS-MDW
$109
2/20Thu
nonstopDelta
2h 33mORD-BOS
2/24Mon
nonstopDelta
2h 59mBOS-ORD
$157
2/28Fri
nonstopJetBlue
2h 23mORD-BOS
3/3Mon
nonstopJetBlue
3h 00mBOS-ORD
$167
3/1Sat
nonstopAmerican Airlines
2h 20mORD-BOS
3/10Mon
nonstopAmerican Airlines
2h 59mBOS-ORD
$176
2/6Thu
nonstopJetBlue
2h 15mORD-BOS
2/10Mon
nonstopJetBlue
3h 03mBOS-ORD
$177
3/8Sat
nonstopAmerican Airlines
2h 13mORD-BOS
3/15Sat
nonstopAmerican Airlines
3h 00mBOS-ORD
$179
3/19Wed
nonstopUnited Airlines
2h 23mORD-BOS
3/25Tue
1 stopUnited Airlines
5h 08mBOS-ORD
$183
2/4Tue
nonstopDelta
2h 29mORD-BOS
2/7Fri
nonstopDelta
2h 59mBOS-ORD
$212
2/4Tue
nonstopUnited Airlines
2h 26mORD-BOS
2/9Sun
1 stopUnited Airlines
6h 07mBOS-ORD
$222

Search by stops

Search by airline

Search by price

Recent one-way flight deals

4/15Tue
1 stopFrontier
7h 07mMDW-BOS
$50
2/11Tue
1 stopFrontier
6h 08mMDW-BOS
$54
2/17Mon
nonstopDelta
2h 33mORD-BOS
$79
2/10Mon
nonstopJetBlue
2h 15mORD-BOS
$89
4/21Mon
nonstopDelta
2h 26mORD-BOS
$99
4/11Fri
nonstopJetBlue
2h 29mORD-BOS
$100
5/16Fri
nonstopUnited Airlines
2h 25mORD-BOS
$104
3/2Sun
nonstopAmerican Airlines
2h 20mORD-BOS
$109
7/22Tue
1 stopAmerican Airlines
4h 26mORD-HYA
$110
2/22Sat
nonstopUnited Airlines
2h 19mORD-BOS
$114

Search by stops

Search by airline

Search by price

Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

1/28Tue
multi-stopFrontier
8h 40mORD-BOS
2/1Sat
multi-stopFrontier
28h 52mBOS-ORD
$120
1/24Fri
multi-stop
10h 10mORD-BOS
1/29Wed
multi-stop
7h 45mBOS-ORD
$125
1/28Tue
nonstopJetBlue
2h 15mORD-BOS
1/31Fri
nonstopJetBlue
3h 07mBOS-ORD
$247
1/28Tue
nonstopJetBlue
2h 15mORD-BOS
1/31Fri
multi-stopJetBlue
5h 16mBOS-ORD
$257
1/25Sat
multi-stopDelta
7h 49mORD-BOS
1/29Wed
nonstopDelta
3h 05mBOS-ORD
$307
1/24Fri
multi-stopDelta
5h 23mORD-BOS
2/2Sun
nonstopDelta
3h 10mBOS-ORD
$332
1/27Mon
multi-stopAmerican Airlines
5h 29mORD-BOS
1/29Wed
multi-stopAmerican Airlines
5h 49mBOS-ORD
$354
1/28Tue
multi-stopUnited Airlines
18h 28mORD-BDL
2/2Sun
multi-stopUnited Airlines
21h 47mBDL-ORD
$678
1/27Mon
multi-stopUnited Airlines
6h 44mSTL-BOS
1/29Wed
multi-stopUnited Airlines
5h 44mBOS-STL
$709
1/24Fri
nonstopAmerican Airlines
2h 06mORD-ALB
1/26Sun
nonstopAmerican Airlines
2h 45mALB-ORD
$787

Search by stops

Search by airline

Search by price

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.