$53 Find Cheap Flights from Illinois to Massachusetts

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Low season

January

High season

July

Cheapest flight

$53
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% increase in price.
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.

  • Which is the cheapest airport to fly into in Massachusetts?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Massachusetts is Boston Logan Intl Airport (BOS), with an average flight price of $144.

  • What is the cheapest day to fly to Massachusetts?

    Based on KAYAK data, the cheapest day to fly to Massachusetts is Wednesday where round-trip tickets can be as cheap as $250. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $329 on average.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally at night, when round-trip flights cost $194 on average. Morning departures are around 12% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $300.

  • What is the cheapest flight to Massachusetts?

    The cheapest ticket to Massachusetts from Illinois found in the last 72 hours was to Boston, at $97 round-trip. The most popular route is Chicago Midway Airport (MDW) to Boston (BOS) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $97.

  • What is the cheapest month to fly from Illinois to Massachusetts?

    The cheapest month for flights from Illinois to Massachusetts is January, when tickets cost $185 (return) on average. On the other hand, the most expensive months are February and June, when the average cost of round-trip tickets is $323 and $322 respectively.

  • How far in advance should I book a flight from Illinois to Massachusetts?

    To get a below average price on the flight from Illinois to Massachusetts, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

  • How long is the flight to Massachusetts?

    An average nonstop flight from Illinois to Massachusetts takes 6h 00m, covering a distance of 888 miles. The shortest route is Chicago Midway Airport (MDW) to Albany (ALB) with an average flight time of 1h 50m.

  • What are the most popular destinations in Massachusetts?

    Based on KAYAK flight searches, the most popular destination is Boston (68% of total searches to Massachusetts). The next most popular destinations are Hartford (18%) and Albany (10%). Searches for flights to Nantucket (3%), to West Tisbury (1%) and to Worcester (0%) are also popular.

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 7920 reviews
7.3Food
8.5Crew
8.2Boarding
7.9Comfort
7.9Entertainment
Airline reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

10.0 ExcellentGary, Apr 2025TPA - LAX
Read more Delta reviews

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

Delayed take-off. Very small plane so very scary with lots of bumps during the flight. Would never fly Delta on short flights in small 80 seaters plane again! Felt relieved when landed.

Delta is a cut above the others in customer service.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

A little bumpy ride . No food was being provided due the the turbulence. That was ok it was a short flight to my standards.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The plane was old with small storage areas that had problems closing/latching and not enough storage for everyone, and worn, damaged seats. Service was great but feel a little unsafe on such well used planes.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Flights on time. .Ride was as comfortable as can be expected in steerage. Luggage arrived at destination. Attendants were fairly friendly.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

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.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

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

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

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.

Worst airline ever! The guy weighing my bag had his foot on the metal plate and when I called him out on it, I got this stupid little smirk. La is a scam and so is Spirit Airlines. All the flight attendants looked like they hated our flight just as much as we did.

Spirit is awful. Too expensive for what you get. Stop nickel and diming.

Good crew and safe. However, comfort and being nickeled-and-dimed are my issues. $75 each way for luggage is exhortation. The space to the next seat is so close you cannot open a laptop. The magazine rack doesn’t hold your items. Not a fan.

We had a 5 hour delay, which resulted in my arriving at my final destination at 2 am instead of 9 pm

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.

Book cheap flights from Illinois to Massachusetts

Recent round-trip flight deals

5/7Wed
nonstopJetBlue
2h 29mORD-BOS
5/13Tue
nonstopJetBlue
3h 00mBOS-ORD
$117
5/10Sat
nonstopSouthwest
2h 20mMDW-BOS
5/11Sun
nonstopSouthwest
2h 35mBOS-MDW
$117
6/6Fri
nonstopAmerican Airlines
2h 40mORD-BOS
6/11Wed
nonstopAmerican Airlines
2h 51mBOS-ORD
$118
5/10Sat
nonstopAmerican Airlines
2h 24mORD-BOS
5/13Tue
nonstopAmerican Airlines
3h 02mBOS-ORD
$119
5/13Tue
1 stopSpirit Airlines
9h 48mORD-BOS
5/20Tue
1 stopSpirit Airlines
8h 15mBOS-ORD
$121
5/31Sat
nonstopUnited Airlines
2h 38mORD-BOS
6/2Mon
nonstopUnited Airlines
2h 58mBOS-ORD
$135
7/20Sun
nonstopUnited Airlines
2h 27mORD-BOS
7/23Wed
nonstopUnited Airlines
2h 51mBOS-ORD
$137
5/14Wed
1 stopSpirit Airlines
8h 39mORD-BOS
5/21Wed
1 stopSpirit Airlines
8h 15mBOS-ORD
$145
6/5Thu
nonstopDelta
2h 25mORD-BOS
6/10Tue
nonstopDelta
2h 49mBOS-ORD
$147
5/31Sat
nonstopDelta
2h 25mORD-BOS
6/4Wed
nonstopDelta
2h 49mBOS-ORD
$177

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Recent one-way flight deals

10/16Thu
nonstopSpirit Airlines
2h 26mORD-BOS
$53
10/16Thu
nonstopSpirit Airlines
2h 26mORD-BOS
$55
5/6Tue
nonstopJetBlue
2h 29mORD-BOS
$59
5/20Tue
nonstopAmerican Airlines
2h 35mORD-BOS
$60
7/4Fri
nonstopUnited Airlines
2h 26mORD-BOS
$76
5/8Thu
nonstopUnited Airlines
2h 24mORD-BOS
$79
5/2Fri
nonstopAmerican Airlines
2h 31mORD-BOS
$89
5/25Sun
nonstopDelta
2h 25mORD-BOS
$90
5/8Thu
nonstopJetBlue
2h 29mORD-BOS
$94
5/25Sun
1 stopDelta
5h 32mORD-ACK
$103

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Last minute flights from Illinois to Massachusetts

Last minute flight, train and bus deals

4/24Thu
nonstopDelta
2h 26mORD-BOS
4/28Mon
nonstopDelta
2h 56mBOS-ORD
$253
4/24Thu
nonstopSouthwest
2h 15mMDW-BOS
4/28Mon
nonstopSouthwest
2h 40mBOS-MDW
$253
4/26Sat
multi-stopAmerican Airlines
4h 01mORD-BOS
4/29Tue
nonstopAmerican Airlines
3h 10mBOS-ORD
$264
4/25Fri
multi-stopAmerican Airlines
4h 52mORD-BOS
4/30Wed
nonstopAmerican Airlines
2h 58mBOS-ORD
$267
4/23Wed
nonstopUnited Airlines
2h 28mORD-BOS
4/29Tue
nonstopUnited Airlines
2h 57mBOS-ORD
$278
4/23Wed
nonstopJetBlue
2h 29mORD-BOS
4/27Sun
nonstopJetBlue
3h 07mBOS-ORD
$283
4/24Thu
nonstopUnited Airlines
2h 28mORD-BOS
4/27Sun
nonstopUnited Airlines
2h 57mBOS-ORD
$323
4/26Sat
multi-stopSpirit Airlines
13h 40mORD-BOS
5/3Sat
multi-stopSpirit Airlines
12h 00mBOS-ORD
$325
4/25Fri
multi-stopSpirit Airlines
13h 03mORD-BOS
4/26Sat
multi-stopSpirit Airlines
12h 00mBOS-ORD
$326
4/23Wed
nonstopJetBlue
2h 30mORD-BOS
4/26Sat
nonstopJetBlue
3h 12mBOS-ORD
$414

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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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