Find cheap flights from Illinois to Massachusetts

Find cheap flights from Illinois to Massachusetts

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

Round-trip
Economy
Boston (BOS)
Massachusetts
Fri 7/30
Fri 8/6
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Good to know

Low season

AugustBest time to beat the crowds with an average 8% drop in price.

High season

DecemberMost popular time to fly with an average 21% increase in price.

Average price round-trip

$419(avg. price over the last 2 weeks)

Good deal round-trip

$57or less

Good deal one-way

$56or less

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Top 5 airlines serving from Illinois to Massachusetts

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,644 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Tv dont work in a fly of 4hr 30 min"

Cons: "Was 2hrs behind schedule"

Pros: "Free wireless"
Cons: "I'm not in Charlotte"

Pros: "Everything!"
Cons: "Great! No improvements."

Pros: "That was great and amazing"
Cons: "The time"

Pros: "Service was awesome, 100% recommended"

Cons: "Freezing cold"

Cons: "Delay"

Pros: "crew was friendly enough, provided the bare minimum of service"
Cons: "running water in the bathrooms hot coffee and tea"

Pros: "Unbelievable for the price."
Cons: "Nothing bad to say."

Cons: "Left very late because of delayed inbound flight and need for deicing."

Cons: "The traffic at LAX is horrible (not JetBlue's fault). It took a good 25 minutes to drive from the entrance of the airport to the terminal. Allow extra time."

Pros: "Loved it."

Cons: "2 hours late!"

Cons: "got to airport and had to pay additional 100.00 because of unaccompanied minor. would have liked to know that at booking. not at airport."

Pros: "Clean plane"
Cons: "Took 3+ hours to get in the plane"

Cons: "The cabin crew was a little lacking and the captain did not mentioned that we had landed almost a full hour later than scheduled."

Pros: "Pilot’s smooth take off and landing."
Cons: "The weather haha."

Pros: "Nice trip affordable price"

Cons: "It really comfy and safe"

Pros: "I liked that the pilot was able to make up some time because our flight was delayed over one hour in Chicago."
Cons: "The notification that the flight was boarding early. I enabled notifications and still did not receive notification that the plane was boarding."

Pros: "Nothing"
Cons: "Being delayed from 6am to 1:30pm"

Pros: "Flight was delayed 30 minutes at takeoff but landed when it was scheduled, so it was fine. Flight attendants didn’t make you stay in your seat, so you could use the lavatory. A fine, uneventful flight. Free WiFi. Snacks. Drinks. Fairly comfortable seats with decent legroom."
Cons: "Wish the seats in front of the emergency exit reclined."

Pros: "The crew was unfailing cheerful and helpful. The seats are comfortable and there’s a little more space than some airlines. The fight and particularly the landing was very smooth. Great experience!"

Pros: "Seat space for each passenger"

Pros: "Turbulence, wait time before landing and staying still for long periods on bothends"

Pros: "crew was supportive. wifi in the flight"
Cons: "the wait time and the boarding, off boarding of the flight. No electricity in the aircraft."

Pros: "Nothing!"
Cons: "IT WAS TWO BOURS LATE!"

Pros: "The crew talked a big game. They were ready for anything, including loss of cabin pressure, paid snacks, and even a water landing."
Cons: "No water landing! I was excited to float around on a hot day, go down an awesome slide, and catch some sick waves, but come on people, we never even got a chance!"

Cons: "could not make it in time. Then we got on plane and pilot said it was an electrical problem on the flight but the generators were now up and at em again. Very hair raising ride for me - got in at 2:30 am with another hour to drive home - and I lost a LOT of confidence which I have always had in Jet Blue. I hope this is not the future we can expect with you"

Cons: "have hearing aids and could not figureout how to turn on CC"

Pros: "Entertainment, food, crew, and cleanliness were 100000% on point. Loved it."
Cons: "Turbulence and the flight was longer than necessary because we had to go around bad weather. Not the fault of JetBlue!"

Pros: "Cheerful, efficient service. No hidden costs. Free gate to gate WiFi. Comfortable seats. Never flown them before and they are now at the top of my list."
Cons: "Nothing yet."

Pros: "The seats were comfortable."
Cons: "Flight was very late leaving Chicago. We sat on the plane for quite a while (over 30 min) shut up tight with little air circulation AND no information about why we were not leaving the gate. Flight crew were not very friendly - almost "marched" up and down the aisle and barked at people."

Pros: "Adequate leg room and ability to take a carry on we if your extra charge"

Pros: "comfortable seats TV great beverages--actually get can or bottle"
Cons: "when we checked it, did not put us together"

Pros: "I dont usually fly, staff was friendly and helpful, made my experience less stressful."

Cons: "No movies just Direct TV."

Pros: "The comfort of the seats are amazing. I was able to sleep through almost all of the flight."

Pros: "No gate, waited 2 hours in plane"

Pros: "Everything is ok"
Cons: "Not a thing"

Cons: "Turbulence was terrible, understand that is not JetBlue issue - wanted to note."

Pros: "Captain and crew"
Cons: "Luggage handling"

Pros: "You took great care of my wife who needed a wheelchair. the flight itself was delayed due to weather. I totally understand. I love the extra legroom"

Pros: "Polite and attentive service Early arrival Thanks"

Cons: "flight was delayed 2 hours :("

Pros: "I had my own row."

Pros: "Overall efficiency of the trip was very good."
Cons: "Audio in seat was poor. Lots of static and could not hear show."

Pros: "Everything"
Cons: "Nothing"

Pros: "Easy"
Cons: "Wifi"

Pros: "Pretty straight forward. Clean. Efficient."

Pros: "Good organization, good hygiene, polite crew."

Pros: "The food and drinks were so lovely, it felt like I was in first class rather than the cheapest economy seat. Great entertainment selection and comfortable seat that let me sleep well."

Pros: "Nothing"
Cons: "Proper communication"

Pros: "Service was great."
Cons: "It was a shortest duration flight of the three so I couldn’t point out here what was lacking. Thank you!"

Pros: "The crew was ok. The seats was good :)"

Pros: "The crew was good. Now fast but good."
Cons: "The food was pretty basic."

Cons: "Wifi didn't work"

Pros: "Food, timeliness, comfort"
Cons: "Not sure"

Pros: "Delta, as always, comes through! Although my original flight was delayed, Delta provided the option to rebook on another DL flight at no additional cost. They made it super easy! As always, the crew was friendly, helpful and professional! Thanks!"

Cons: "WiFi didn't work"

Pros: "Convenience. Smooth ride. On time. Great staff."
Cons: "N/A"

Pros: "Nicer plane"
Cons: "One stewardess almonds mowed me down with cart"

Cons: "At least one hour late"

Cons: "Wheelchair shortage on arrival, although I had one reserved. Waited for a while then walked. Not ideal. Very long wait for bus to rental car center."

Pros: "I liked the cookies and juice. The interactive screen to watch something. The cleanliness. The price. On time. The service. Thank you. The excitement of flying."

Pros: "Not comfortable and not helpful"
Cons: "Some rude staffs , not helpful"

Pros: "On time and helpful staff."
Cons: "Very cramped seating."

Pros: "Everything was really great"
Cons: "I can’t no say anything bad"

Cons: "Really rough landing"

Cons: "Late boarding and take off with no explanation."

Cons: "Dripped on!!!!!!"

Pros: "I am always impressed by the Delta staff. Top notch."
Cons: "The entertainment screens have an (older) head phone jack that many people do not have. The headphones available for purchase by the airline are of very poor quality. I also am surprised that airlines (not just Delta) continue to provide such low quality food options on flights. I think consumers would pay more for better options."

Pros: "On time, staff, and overall service"
Cons: "No complaints"

Pros: "Awesome customer service"
Cons: "No complaints"

Pros: "Me atendieron muy bien , tuve un excelente viaje"
Cons: "Nada"

Pros: "Even though we were in the very back row, we did not experience a foul smell from the restrooms. This was a very nice relief. It is bad enough that the seats don't recline and there is no window in the very back row but prior experience with the added nausea of foul restroom order has been a serious insult to injury. In this case there was really minimal odor. Also since we are traveling as a family we are very happy that we were seated together. We have experienced the past that sometimes our seats will be fragmented and that creates major challenges when you are traveling with young children. However on this particular flight the ride was rough during both takeoff and landing, a lot of side to side shimmy. Also the cabin pressure varied quite a bit during landing causing all the kids to complain about some discomfort in their ears."

Pros: "Loading process, seats and drinks were great"
Cons: "No TV on back of the seat but thankfully the ladies next to me were very entertained"

Pros: "The TV selections"

Cons: "Change d for WiFi. Cheap"

Pros: "I liked the WiFi and Movies. The flight crew was wonderful making a stressful retreat from Hurricane Irma a little better"

Pros: "Clean and good size sears"
Cons: "Slow boarding, crew tires and it showed, pretzels no nuts,"

Pros: "Efficient hop to Boston"

Pros: "Modern plane from ATL to BOS. On board games were a fun distraction."

Pros: "Free entertainment and free food was unexpected and very welcomed, especially given the trend of charging for more and more features."

Cons: "The tsa is worthless"

Pros: "They did eventually put out some small snacks and drinks (water and regular coke)."
Cons: "Small regional plane that was over 3 hours late in departing NY because of weather issues much earlier in the day. Delta did not permit any re-bookings to other delayed flights that were leaving in the intervening period, even though there were empty seats. Very frustrating."

Pros: "Very professionals"
Cons: "N/A"

Pros: "Everything went smoothly."
Cons: "N/A"

Pros: "Easy boarding. Due to bad weather they kept us well informed. One hour late but not their fault."
Cons: "A little chilly in the waiting are."

Cons: "Smooth and easy"

Cons: "Boarding in LA was. Mess"

Pros: "The crew were nice"
Cons: "The wifi didn't work at all, the entertainment system wasn't working until they did a reboot during the flight"

Pros: "I'm surprise that Delta airline serves free dinner for domestic flight, which is definitely a compliment. I would travel with Delta airline again"
Cons: "n/a"

Cons: "No tvs."

Pros: "On time departure and arrival."
Cons: "Cramped! Cabin crew not particularly friendly."

Pros: "Great stewardesses, good food"

Cons: "All good"

Cons: "Same as above"

Cons: "Entertainment system nor working properly. 40 minute flight delay due to minor cabin seat malfunction."

Cons: "We need food"

Pros: "yes"
Cons: "nothing"

Pros: "I had a great seat"
Cons: "Attention to detail by the gate attendant who totally missed that I was boarding the wrong flight"

Cons: "Leave a seat empty in the middle could be good for social distancing"

Cons: "Foood"

Pros: "The crew was nice"
Cons: "American has been overbooking flights, doesn't respect social distancing, not true that the middle seat is empty, the person next to me coughed frequently, and since it was a FULL flight, I couldn't get another seat!, never again American"

Pros: "Very timely and efficient"
Cons: "Seats are really small"

Pros: "That it arrived eventually without crashing"
Cons: "Boarding. Sitting on a tarmac in hot stuffy plane for 40 min is not why I was looking for"

Pros: "That I took off and landed safely."
Cons: "The attitude of the employees."

Pros: "Amazing Crew"

Pros: "Nothing special."

Pros: "Quick boarding, nice plane, tv at every seat."
Cons: "T.v. kept getting interrupted, and the automated voiceover would be followed by a person saying the same thing."

Pros: "Did not experience food or entertainment"

Pros: "Great crew again, basic aircraft but comfortable economy seats."

Pros: "On time!!!"
Cons: "Small chairs."

Cons: "Had to drive 100 miles to catch second leg of trip."

Cons: "Six “10 min delays” that led to a 1 hr plus delay"

Pros: "The crew was very kind."
Cons: "There was an issue where someone had boarded and somehow taken my seat. I was asked to wait until the very end and then allowed in my seat once the passenger in my designated seat was asked to deboard the plane. I don't know how that could have happened."

Pros: "Or some attitude re-adjustment. I usually observe rude passengers acting the way some of the stewards were acting."
Cons: "Rude staff"

Cons: "Have to pay for WiFi"

Cons: "The 24hr layover in Miami"

Cons: "No entertainment, nor food"

Pros: "Quick and easy"
Cons: "N/A"

Cons: "They misplaced my luggage and it did not arrive in Boston"

Pros: "Liked that there were easily accessible power ports"
Cons: "My entertainment system did not work"

Pros: "Everything"
Cons: "Nothing"

Pros: "Outlets, great entertainment choices, quick boarding"

Pros: "On time arrival"

Pros: "Overall easy navigation."
Cons: "More signs for terminal to terminal navigation."

Pros: "I actually got to sit by my sweetie. Perfection."

Pros: "Gate flight updates"
Cons: "No information on luggage even though they knew luggage was not received in London They could have sent me an update instead of having me wait at carousel for 1:30 hours waiting for my bag to show up"

Pros: "Staff was polite and friendly. It was a great experience!"

Pros: "The entertainment was updated and refreshing."
Cons: "Snacks was only pretzel"

Pros: "Everyone operated fast and professional"
Cons: "Nothing"

Pros: "Allowed us to pre-order with our daughter who needed our support."

Pros: "Newer Aircraft had a little more legroom than I have seen in the past. Complimentary entertainment was excellent. It made the time on the ground and in the air go by quickly (even on this short flight)."
Cons: "Time on the ground waiting for takeoff. We spent more time on the ground than in the air. But that is more the congestion at the airport than the airline."

Pros: "It did not crash"
Cons: "Delays, baggage loss, how the Airline dealt with both."

Cons: "The seat was extremely comfortable."

Pros: "It was a reminder again why I never fly United"

Pros: "It's fine, you know what to expect."
Cons: "No entertainment; no TVs, no music."

Cons: "Served drink as they prepped for landing"

Pros: "Quick, easy, great crew"

Pros: "Entertainment system has a good selection"
Cons: "No earphones to listen to the soundtrack on the entertainment system"

Cons: "Delayed for 30 mins due to traffic going in to Boston."

Cons: "Old plane"

Pros: "Everything was good or better."
Cons: "No dislikes"

Pros: "On time"

Pros: "Very comfortable flight. All I did was sleep and watch movies, it was great."

Cons: "AA flights always seem to get delayed. I never fly AA unless I have to."

Cons: "Wish we had arrived on time we are an hour and a half late"

Pros: "Crew was great!"
Cons: "Boarding was excruciatingly slow."

Pros: "The crew was super nice and helpful. They made an effort to answer any questions the passengers had. They made the flight home very enjoyable. I plan to fly with Allegiant again."

Cons: "Great crew and smooth ride"

Pros: "The passengers were spaced out, so we could actually social distance."
Cons: "Not all passengers wore masks. During a contagious pandemic. What the actual hell? Also, the tray tables are too small to use for anything, and we didn’t even get a free drink. Water and soda are so cheap, it’s absurd. I’d never take Allegiant again if they weren’t basically the only airline operating out of my town’s small airport."

Pros: "Crew was Aamazzing! Went above and beyond even to sit with one of kids while I used restroom, put my kids at ease, went above and beyond to make sure at such a tender age that they were okay! Made me very happy with allegiant and happy that I chose them!"
Cons: "It’d be cool to see more inflight services some day? As in maybe WiFi at a cost or TVs, seat recliner"

Cons: "Free beverages"

Pros: "Boarding was super smooth,"
Cons: "Offer some type of entertainment, ie internet or something"

Pros: "Not bad for the price, convenience beats all"
Cons: "First class"

Pros: "Nice crew. Friendly and responsive"
Cons: "Recliner chairs"

Cons: "Unclear pricing for carry on bag, could have saved $30 by paying at the ticket counter (even though I was sent an eticket and boarding pass); got stuck paying $50 at the gate."

Pros: "Price and timeliness"
Cons: "Airline broke the stroller we had. That could have gone better."

Pros: "No The crew was not friendly at all"
Cons: "I honestly am angry that I was charged for things others where not.This is ridiculous"

Pros: "Nothing, honestly. Constantly delayed, cheap airline with forced fees, only one I could take and I can’t believe you exist. You have horrible customer service"
Cons: "I will never fly you again. Sure you don’t care."

Pros: "The flight attendants, the space on the plane, the prompt departure and arrival!"
Cons: "Media has not been reflective of my great experience."

Pros: "Boarding was better than other airlines."
Cons: "Seats are uncomfortable and do NOT recline!"

Pros: "One hop flight"
Cons: "cramped seating, no wi-fi or on flight entertainment, low class of traveler, noisy older model aircraft,"

Cons: "The flight was delayed all day!!!"

Pros: "Quick and easy boarding, on schedule and the cleanliness of the cabin."
Cons: "Extra charge to make use of the overhead bins. This does not include extra work or cost for Allegiant. Lack of legroom; take out two rows of seating and make the current size of travellers comfortable."

Cons: "Long wait due to plane speaker malfunction. Offered free drink pours on flight once we finally took off but it was a very small “2 sip” pour."

Pros: "Cheap fare, nice crew, clean plane"
Cons: "Small seating, small snacks , extra charges for anything"

Cons: "Flight was very late. Have to pay $45 for a carry-on bag. Seats were uncomfortable and have to pay for all snacks and drinks including water."

Pros: "My kids and I had great experiences with Allegiant Air, thanks in large part to some excellent flight attendants. This was the first flight for both of my children (5, 7) and they had a blast. On our initial flight from Indianapolis to Ft. Lauderdale the attendants even gave each of them their own set of pin-on wings since it was their first time. The kids loved this!"

Pros: "The price."
Cons: "Everything about Aligiant is horrible. Service, attitude, even the pilots can’t land smoothly. As a diabetic, they don’t even give you water withiit paying for it. Had my wallet in my checked bag and almost had a health issue."

Pros: "The staff and crew are extremely polite and focused on good service."
Cons: "The seats on the Allegiant MD-80 don't recline AND the space between one row and the next is EXTREMELY tight. Much tighter than I have seen in an airline in a while."

Cons: "baggage staff was super rude. She told me I am the last passenger on the plane which wasn't true. She made me pay $50 because of little overweight. I could easily redistribute the weight among my bags if she gave me little chance. I was a single mom with two kids (3 months and 3 years old) had to pay a fine which I can't afford. Thanks for giving me the chance to express my feelings."

Pros: "friendly helpful staff. on time. safe."
Cons: "my suitcase went to the WRONG destination. very inconvenient and expensive. also plane interior was pretty shabby which made me wonder about the engines, mechanical etc."

Pros: "I fly this airline airline quite a bit because I have family in the mountains of North Carolina. I have never had a problem with them, I fly out of Fort Lauderdale to Asheville, it's a quick one and a half hour flight. The flight crew is always professional and courteous."

Pros: "On time and pleasant crew."
Cons: "Old plane,"

Cons: "Flight cancelled on the way to the airport due to weather. Weather wasn't due to turn bad for 36 hours."

Pros: "Flight went smooth"
Cons: "I checked into my flight with luggage to check in. The lady behind the counter said I could not check my luggage that the only way for it to get on the plane was to take it through the TSA checkpoint. They confiscated everything in my bag that was over 3oz which was quite a bit of stuff hence the reason why I was trying to check it in. I will not be flying Allegiant air again."

Pros: "I arrived safely Tommy Destination"
Cons: "It was so hot boarding and unloading. There was no air. Staff was curt and not very friendly as of assistance."

Pros: "The plane was clean"
Cons: "You have to pay to choose your seat, to have more than one carry on bag (literally of any size!!), and for any food. Nothing is complimentary. The seats don't lean back at all. No headrest adjustment for any sort of comfort. The seats are hard. We had a 30 min. Delay for some reason we were not made aware of and no apology was made. No Tv's or even a pocket in the seat-back in front of you. Basically if you can fly anything else other than this airline you are probably better off. Delta is basically the exact opposite of this airline and even American does way more. If I can help it I will never use this airline again."

Pros: "Very efficient service... for a first experience we were pretty impressed because your review overall were not that great. Good job."
Cons: "The airline nickel and dimes for everything."

Pros: "Considering the fare was advertised between $350 and $700 with other carriers on Kayak, I took this one for $179, roundtrip, direct from LAX to Grand Junction."
Cons: "When the crew runs to get coffee in the terminal, make sure to do the same. I brought some snacks, but wish I had brought coffee. The man next to me kept creeping into my space which was incredibly annoying, but it was a relatively quick flight. Beats the two day drive from L.A. to Colorado."

Cons: "First they delayed the flight and then they cancelled the day of and I had to book a whole new flight for the day which was costly. I will never recommend that airline to anyone and I wanted to like it since I looked at their website and it looked very military friendly, but it was just disappointing"

Pros: "Quick boarding with priority access Friendly staff"
Cons: "Unclear boarding instructions. Both flights roundtrip were delayed about an hour. Wasn't advised of seat changes and reasons why. Mobile passes were unavailable due to a system issue gate attendants had to check manually. Bring own snacks or eat before flight and provide your own entertainment. Seats not reclining are uncomfortable. Not suitable for someone with back issues. First flight was uncomfortably cold return flight was uncomfortably hot."

Pros: "Everything was good"
Cons: "Could of had more selections on the flight for snacks"

Pros: "Well, it was a somewhat inexpensive flight out of a convenient terminal."
Cons: "I say somewhat cheap, because by the time they ala carte everything, it's not so cheap anymore. As in no longer cheap enough to justify the bare bones service. The flight attendants are basically candy salespeople. I typically need help putting things in the overhead bin, but the flight attendant actually told me it wasn't her job. That indeed may be the airline's bad policy, but she also thought her way of expressing it was appropriate, which it is not. That has to come straight from the top. Also, what kinda janky airline doesn't serve complementary water. Probably the biggest deal though was that my flight was delayed for 2 hours both ways due to a maintenance issue. I know air travel is fairly safe, but given the track record of both Allegiant and Airbus, I was a little worried during the flights. Even though this particular route is convenient for me, I'm going to avoid Allegiant."

Pros: "Nothing"
Cons: "I paid for 1A. Was moved because "the crew needed the seat" to the middle. There were SO many open seats. Was unacceptable."

Cons: "Our flight was delayed dor 10 hours."

Pros: "No complaints about the trip to Newqrk. Everyone was very helpful and patient since I am an unexperienced flyer."
Cons: "I didn't like thinking I was paying one price then paying another or buying insurance that would have been useless since it doesn't cover anythIntg."

Pros: "The price of the flight was cheap, but i know why. You ended up paying for your carry on luggage, ypu pay for seat assignment if you want to guarentee sitting with you party, you pay for soda. My flight was 1.5 hours late, due to mechanical problem. Plane was janky and it felt like it STILL needed repairs."
Cons: "Low airfare."

Cons: "Even snacks and water are only available for a fee. Seats do not have much padding and are not comfortable."

Pros: "We eventually got to Las Vegas."
Cons: "Everything. Spend an it make and book with someone else."

Cons: "Having to pay for drinks. But, I didn't even not mind it that much. I'd much rather a cheaper flight"

Pros: "Evertything was on schedule ."

Pros: "Didn't have any problems. Flight was on time departing and returning and non-stop."
Cons: "When I booked my flight, the website didn't give me an option of whether I had a carry-on or checked bag."

Cons: "I was charge $24.00 for internet and it was too slow. No meals to purchase"

Cons: "Significant delay-no weather issues, didn't make sense."

Pros: "On time"

Pros: "That I got home."
Cons: "See above."

Cons: "It appears united is unable to fly their planes on times, in particular on the East Coast. We were delayed by 90min on each legs"

Pros: "It was quick and on time."
Cons: "Nothing."

Cons: "The seating and chance to keep my luggage"

Cons: "Still have not left."

Cons: "No leg rooom"

Cons: "The staff does not respect or bother if it is full filght"

Cons: "18 mini pretzels. really?"

Pros: "None"
Cons: "Seated near a crazy patient"

Pros: "Crew help and service"
Cons: "Lending was bumpy. , Internet was not Working and no entertainment chenal as well"

Cons: "Flight was full to capacity"

Cons: "Because of missed connection I had to go from Dulles to Reagan airport"

Pros: "It was ok"
Cons: "Too much confusion on seating...people were moved because of double seating then I was asked to move I seat back. I only agreed so the parent could sit with his two children"

Pros: "Boarding process did not take long"
Cons: "Rough landing"

Cons: "Snack was terrible"

Pros: "It was great arriving 20 min early, but no wifi!"

Cons: "No legroom. Sat TV cut out constantly"

Pros: "Food vouchers were nice. $20 did not cover lunch and dinner for that day. So it coupd have been more like $40."

Pros: "The check in was great. The staff was very helpful."
Cons: "The plane was very small and hot. There was no space for even my legs."

Pros: "Same"

Pros: "Very rough conditions into BOS, pittsfield did great job."

Pros: "I was wirried about making the connection. Enddd up with an hour which was ample."

Pros: "Enough time to walk from gate to gate."
Cons: "Had to pay for wifi while waiting."

Cons: "We were told there wasn't anymore space for carry ons so I had to check my bag. I got on the plane and there was plenty of space for bags. There needs to be better more efficient communication about baggage space."

Pros: "Departed on time, arrived 1/2 an hour earlier than anticipated."

Pros: "Delay, delay, delay"

Pros: "Good pilot landed nicely in rough weather"
Cons: "Last minute Gate change and delays."

Pros: "Lovely, comfortable"

Pros: "Well organized"
Cons: "No free wifi :("

Cons: "There was a delay after boarding / door closing. We just sat at the gate without explanation so we arrived late in Boston. I assume we were held for some reason by the tower but an update from the pilot would have been nice."

Pros: "Roomier comfortable seating."
Cons: "Paying for luggage and food"

Pros: "At least there was room to sprawl out and rest."
Cons: "We boarded our plane and during preflight check on the runway the captain learned there was mechanical error (in the right engine fuel something). The issue could not be solved and we had to change planes. On the second plane, the captain shared with travelers that "and two loose wires were found, so it's good we caught that and changed planes". What the heck? Shouldn't basic functions be checked before a plane is boarded? What was supposed to be a 1030 red eye, turned out to be a 1 AM bloodshot eye."

Pros: "Direct tv"
Cons: "None"

Pros: "On time"
Cons: "Food quality"

Pros: "Nothing."
Cons: "Everything."

Cons: "The lack of breakfast options. Lack of room."

Cons: "Everything."

Pros: "They were on time."
Cons: "It was very uncomfortable."

Pros: "Delayed a lot"

Pros: "On-time flights"

Cons: "Delays"

Pros: "I did have a nice trip!"

Pros: "Missed a whole day with grandchildren"

Pros: "Liked the upgrade to first class"

Cons: "Great employees!"

Pros: "The United terminals are amazing. The United planes are not."

Pros: "It was on time and the lights were dimmed so I could sleep better. The staff was also very friendly and helpful."

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Illinois to Massachusetts

Airlines flying from Illinois to Massachusetts have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from Illinois to Massachusetts

Mandatory masks

Masks required on board, masks provided on flights from Illinois to Massachusetts

Social distancing seating

Middle seats unavailable to book on flights from Illinois to Massachusetts

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Illinois to Massachusetts

Book cheap flights from Illinois to Massachusetts

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Spirit Airlines
8h 56m
ORD - BOS
8/27
Fri
1 stop
Spirit Airlines
11h 46m
BOS - ORD
8/24
Tue
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/28
Sat
1 stop
Spirit Airlines
8h 59m
BOS - ORD
8/24
Tue
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/26
Thu
1 stop
Spirit Airlines
8h 59m
BOS - ORD
8/25
Wed
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/26
Thu
1 stop
Spirit Airlines
8h 59m
BOS - ORD
9/1
Wed
1 stop
Spirit Airlines
8h 15m
ORD - BOS
9/4
Sat
1 stop
Spirit Airlines
11h 46m
BOS - ORD
8/25
Wed
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/28
Sat
1 stop
Spirit Airlines
11h 46m
BOS - ORD
9/10
Fri
1 stop
Spirit Airlines
7h 03m
ORD - BOS
9/12
Sun
1 stop
Spirit Airlines
7h 29m
BOS - ORD
8/17
Tue
nonstop
Multiple Airlines
2h 26m
ORD - BOS
8/26
Thu
1 stop
Multiple Airlines
8h 59m
BOS - ORD
9/1
Wed
1 stop
Multiple Airlines
8h 15m
ORD - BOS
9/5
Sun
nonstop
Multiple Airlines
2h 41m
BOS - ORD
9/9
Thu
1 stop
Multiple Airlines
8h 23m
ORD - BOS
9/14
Tue
nonstop
Multiple Airlines
2h 50m
BOS - ORD
9/1
Wed
1 stop
Multiple Airlines
8h 15m
ORD - BOS
9/5
Sun
nonstop
Multiple Airlines
2h 41m
BOS - ORD
9/7
Tue
1 stop
Multiple Airlines
8h 56m
ORD - BOS
9/11
Sat
nonstop
Multiple Airlines
2h 50m
BOS - ORD
10/23
Sat
nonstop
JetBlue
2h 26m
ORD - BOS
10/26
Tue
nonstop
JetBlue
2h 59m
BOS - ORD
9/29
Wed
1 stop
Delta
5h 41m
MDW - BOS
10/5
Tue
1 stop
Delta
4h 05m
BOS - MDW
9/14
Tue
1 stop
Delta
5h 41m
MDW - BOS
9/28
Tue
1 stop
Delta
4h 22m
BOS - MDW
9/2
Thu
1 stop
Frontier
17h 43m
STL - BOS
9/6
Mon
1 stop
Frontier
8h 26m
BOS - STL
11/2
Tue
1 stop
American Airlines
4h 19m
BMI - BOS
11/7
Sun
1 stop
American Airlines
4h 52m
BOS - BMI
11/11
Thu
1 stop
United Airlines
21h 25m
PIA - BOS
11/16
Tue
1 stop
United Airlines
23h 36m
BOS - PIA
8/5
Thu
1 stop
Allegiant Air
17h 30m
MDW - BOS
8/12
Thu
1 stop
Allegiant Air
8h 36m
BOS - MDW
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Recent one-way flight deals

9/22
Wed
1 stop
Spirit Airlines
10h 01m
STL - BOS
8/24
Tue
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/27
Fri
1 stop
Spirit Airlines
9h 15m
STL - BOS
9/22
Wed
1 stop
Spirit Airlines
10h 01m
STL - BOS
8/25
Wed
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/26
Thu
1 stop
Spirit Airlines
8h 56m
ORD - BOS
9/1
Wed
1 stop
Spirit Airlines
8h 15m
ORD - BOS
8/26
Thu
1 stop
Spirit Airlines
8h 56m
ORD - BOS
8/16
Mon
nonstop
JetBlue
2h 26m
ORD - BOS
8/11
Wed
nonstop
JetBlue
2h 26m
ORD - BOS
8/29
Sun
1 stop
Allegiant Air
16h 13m
MDW - BOS
9/19
Sun
1 stop
Allegiant Air
16h 10m
MDW - BOS
8/19
Thu
1 stop
Allegiant Air
16h 13m
MDW - BOS
9/28
Tue
1 stop
American Airlines
7h 34m
ORD - BOS
10/2
Sat
1 stop
Delta
6h 22m
MDW - BOS
9/18
Sat
1 stop
Delta
8h 27m
ORD - BOS
8/30
Mon
1 stop
Frontier
26h 48m
ORD - BOS
9/3
Fri
1 stop
Frontier
16h 38m
STL - BOS
8/3
Tue
1 stop
United Airlines
4h 46m
ORD - BOS
8/30
Mon
1 stop
Multiple Airlines
12h 08m
PIA - BOS
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