Find cheap flights from Massachusetts to Florida Keys

Search hundreds of travel sites at once for deals on flights to Florida Keys. Bundle your flight + hotel and save!

— Florida Keys
Sep 24 — Oct 11
Round-trip
1 adult
Economy
0 bags
From?
To?
Fri 9/24
Fri 10/1

Good to know

Low season

AugustBest time to beat the crowds with an average 3% drop in price.

High season

DecemberMost popular time to fly with an average 18% increase in price.

Average price round-trip

$304(avg. price over the last 2 weeks)

Good deal round-trip

$118or less

Good deal one-way

$59or less

FAQs for booking flights from Massachusetts to Florida Keys

  • American Airlines and JetBlue have all waived their change and cancellation fees on flights from Massachusetts to Florida Keys. Confirm policies on booking site.

  • 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 Massachusetts to Florida Keys.

  • KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Florida Keys from Massachusetts is likely to change within 7 days, so travelers know whether to wait or book now.

  • 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 Florida Keys with an airline and back to Massachusetts with another airline.

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

Top 4 airlines serving from Massachusetts to Florida Keys

Scores according to KAYAK customer reviews
8.1
JetBlueOverall score based on 19751 reviews
8.3Boarding
8.2Comfort
8.6Crew
7.9Entertainment
7.8Food
Airline reviews

Cons: The video screen at my seat did not work. Otherwise the flight was great

Read more about JetBlue

Cons: The video screen at my seat did not work. Otherwise the flight was great

Pros: A flight on time.
Cons: Better explanation on delay. No tv for first 90 minutes

Pros: The crew was amazing and I couldn't believe the pilot came out to help clean the cabin. The friendliest team ever!!
Cons: My second leg of the trio Orlando to Ponce was a nightmare.

Cons: The delay was almost unbearable

Pros: Got some sleep
Cons: More sleep

Pros: Crew was very kind and helpful
Cons: Gate was changed at the last minute

Pros: Seat super comfortable for the price
Cons: Delayed, delayed, delayed and no entertainment on the plane

Cons: There was a 1 hour delay

Pros: Nice pilot -Jim.
Cons: Multiple delays & gate changes

Pros: Crew was amazing and helpful. Flight was smooth. Chairs were comfy. We got home 30 mins ahead of time
Cons: Nothing. I thoroughly enjoyed it

Cons: If the flight leaves at the scheduled time.

Cons: We sat on the plane for an hour for a broken seat table. The internet didn’t work the whole flight

Cons: Therer were four different planes listed leaving at my gate at one time. I was eventually moved two times to different gates. Outbound flight delayed almost an hour and the terminal was extremely overcrowded. Return flight was delayed almost four hours. No notifications made of delay prior to arriva

Pros: Nonstop
Cons: Tv selection

Cons: Boarding was by groups but ended up being 2 different lines of people merging into one. I felt as though boarding should be smoother/more organized.

Pros: Everything was good, no problems at all

Pros: Flight and efficiency.

Pros: Everyone was friendly and kind. The flight was on-time.
Cons: Nothing to complain about.

Pros: How calm the staff remained in the face of many very tired and disappointed people
Cons: The flight had a mechanical issue but no mechanic was duty. the flight was supposed to leave at 5, we left at midnight on a plane flown up from Boston. We arrived at 3 in the morning which left me at 61 driving an hour home at a terrible time of night. I was afraid for my safety driving at that hour but they strung us along for so long there were no real opportunities to choose another option. Besides which my bag was stuck in the broken compartment and could not be retrieved. The flight, when it finally left was so cold that everyone was huddled down in their seats, the very senior lade next to me was pitiful. All in all a horrible experience.

Cons: I paid for extra space and there was none available on my flight.

Pros: The team did their best to board the passengers and expedite cargo.
Cons: Delay. Wasn't sure if pillows had to paid for.

Cons: Once again, on this flight, I, my wife, and our 2-year-old were split up. This time, we were all placed in different rows. Way to go JetBlue! Thankfully, on this flight we had people who were decent enough to trade seats with us (probably because it was only two seats to an aisle, and therefore, no middle seats) so we could be together. Shouldn't have to do this though. PUT FAMILIES TOGETHER ON PLANES, ESPECIALLY IF THEY HAVE YOUNG CHILDREN.

Pros: Good crew, good service, excellent flight

Pros: —
Cons: Why isn’t there enough checked bag space?? Why did 15 people have to check their bags at the gate — and then there STILL wasn’t room?? Why was the CHIP container taking up space in the overhead bin? There has to be a better solution, JetBlue. Do not check my bag after I brought it onto the plane and found a spot. The CHIPS should not be your priority — your customers should be.

Cons: Had to check bag because no available room left

Pros: The face masks were great. Free wifi was very nice. Inflight entertainment were recent movies.

Pros: they were rude
Cons: they were rude, horrible service, unapologetic

Pros: We were delayed by over an hour on our flight to Bosand then delayed, undelayed and then sat on plane waiting for another crew for over an hour. Jet Blue we expected better from you.

Pros: Everything..

Pros: The crew

Pros: Good entertainment
Cons: Four hours late

Cons: Baby is yelling

Pros: Made up time
Cons: I think they should give the headphones and not charge.

Pros: I enjoyed the beverage options and my neighbors
Cons: No complaints

Pros: Good

Pros: Good service
Cons: Flight delayed weeks before leaving then delyet three times on the day of flight

Pros: Weather and atmosphere in Orlando!

Pros: I didn’t die.
Cons: The 6 hour delay. The over tired, but outright rude crew in both the airport and plane.

Pros: Crew member had a great sense of humor.

Pros: There was nothing that stood out in a positive way
Cons: We had to unboard the flight because the plane had no fuel or something, and the interior of the plane was very old and outdated. No charger ports for your phone, terrible tiny screen with very limited choices in television, etc

Pros: Comfortable, great service. We were headed home in bad weather and were anticipating the possibility of cancellation, but the flight was just delayed a few minutes. Then there was a mechanical issue and we had to deplane and were moved to a new plane which got us home 3 hours after originally anticipated. But then we all got $75.00 gift certificates, so it was all good.

Pros: This has been my worst flying experience ever. I arrived to the airport at 9:30 pm for my 11pm flight. Long story short, I was told repeatedley by jet blue and tsa that there is no issue and that the flight was not going to leave without me. Ii ask several times that they please move me to the front to make it to the gate before closing. After being assures several times by tsa and jet blue staff i was okay, i finally made it to the gate and lo and behold, its closed,

Pros: how much training is provided to flight attendants for listening skills?
Cons: uncomfortable seat

Cons: Boarding time and crew was slowest ever?!!!

Cons: Onboarding crew was a bit rude and rushing everyone. Forcing people to check in bags even though there was still space in the overhead bins.

Cons: 1/2 hr late

Pros: easy airport to navigate, quick flight.

Cons: That there were no alternatives

Pros: the atmosphere, appearance of lga, the wheelchair service attendants-kind, courteous and attentive.

Pros: Crew members were nice and professional.




Pros: Seat very v=comfotable

Pros: Plane was new and equipped
Cons: In first class we had beef jerky for breakfast

Pros: Sanitized, open middle seats, comfortable
Cons: We were stuck on the tarmac for 40+ minutes due to our gate being blocked by another plane. We almost missed our connection and had to run through the airport with our luggage and the staff at our second gate yelling “hurry up” at us like it was our fault.

Pros: Friendly crew

Cons: None

Pros: Great crew.

Pros: Everything! the best part was that the they kept the middle seat empty!
Cons: nothing

Cons: For some reason, we were asked several times for Passports. This didn’t make any sense since we are US citizens with drivers license. They even had TSA talk to us. This has to be fixed. Otherwise, Delta experience was great.

Pros: Don’t go overboard
Cons: Cleaner

Pros: Good
Cons: Good for now

Cons: Top carrier

Pros: Well organized and easy to check in.
Cons: No

Cons: Nothing, really. Airlines unfortunately can’t make people patient or polite, & I can’t afford a private jet, so I’ll have to settle for an eye roll or twelve.

Pros: Everything
Cons: Nothing

Cons: The inoperative TV screens should be repaired.

Pros: Was boarded promptly

Cons: During this trip all my flights got delayed and I was told that I could not get a hotel room and had to pay for myself.

Pros: Entertainment. Flight attendants. Food
Cons: PROBLEM WITH LOCATING BAGGAGE CAROUSEL. GIVEN WRKNG LICATION .

Pros: You know what you are getting with Delta
Cons: The economy seats were really tiny, this made the flight fairly uncomfortable

Cons: Plane was late taking off. Crew did not provide water when requested. They were busy with beverages that they could sell at a cost.

Pros: Crew was amazing. Pilots were attentive to kids and answered questions. Everyone was very welcoming and helpful.
Cons: They didn't have some of their food options (and they apologized for that up front), but then ran out of the others by the time they got half way through the plane. That was tough for a five hour flight that went through dinner time.

Pros: Flight was on time. Crew was jovial and very pleasant. Smiles all around. Flight attendant at the very beginning said, "Welcome to flight --- to Bahamas. . . just kidding." It made people chuckle.

Cons: The flight attendants were quick with the pick up of drinks. I had only been served my drink for five minutes and they were already coming around to pick up trash.

Pros: Ryan was great! Very nice and professional, would love to see him on a future flight.

Pros: Smooth flights and in time. Everyone is so nice. True professionals

Pros: Seating was fine
Cons: Did not have a wheelchair waiting for my wife when we arrived in LAX

Pros: Good flight in air

Pros: Everything was great. Has nothing to do with the airline, just rough weather.
Cons: The stewardess could come around more. Just twice. Once for food. Once for trash. Just me tho

Cons: Even the baggage was quick (highly unusual for Columbus, Ohio)! Everything went smoothly.

Pros: The flight attendants were excellent. The plane was comfortable, as usual. The choice of snacks is great!
Cons: Actually, everything was fine. No need for improvement .... even the airfare was great!

Cons: Delays due to Democrats not making deal

Pros: Good service this morning
Cons: All good

Pros: Everything went great. Flight left a little late but was fine and only arrived a little late. I like the side wings on head rests really help.
Cons: Seats are always hard on long flights.

Cons: Delays, delays, delays... first class ticket from BOS to MSP got me a 6 hour delay and a middle seat in econ main cabin at the back of the plane. Delta you suck!

Pros: Got to London on-time (early, actually) and safely. The in flight meal was okay. The leg room in comfort plus was great, the mobile app was awesome, and the staff (check-in, gate, cabin and flight deck) were professional and friendly all around.
Cons: The leg room was great, but as a broad-shouldered guy, the width of the seat was miserable. Unfortunately, the Delta 767 doesn't offer any upgrade for a wider seat beyond Delta One, and my employer won't spring for that. Too bad there isn't a premium economy option. Also, the entertainment unit in the seat next to mine malfunctioned, which you wouldn't think would impact me that much except that because it was "seeing" touches randomly throughout the flight, the screen would turn on, off, brighter, dimmer, play random stuff, and just generally be as annoying as possible to everyone nearby throughout an overnight flight.

Pros: Generally, Delta is cleaner, their terminals are much nicer, and the experience is better than one with American and United. I wish they had more direct flights to my normal destinations--I'd fly with them more!
Cons: Someone unloaded a lot of crumbs on my tray table and they all got smooshed on the back of the seat between the tray table and chair. It was pretty nasty. (The tray table was clean, the back of the seat wasn't. Please be nasty.)

Cons: Tray table was broken, I was downgraded from Comfort plus to main cabin after a plane swap with no mention by anyone and no compensation. Flight was delayed 45 minutes because a flight attendant was running late and then to top it off, at the end of. The flight the attendants blocked anyone fromaim cabin from leaving until all of first class had departed, even when no one was coming they still Blocked it off. This is a practice I have never seen on delta and haven't seen in aviation in almost 20 years in the US

Pros: Leg room and seats are very tight and I'm a small person.
Cons: Coach class is very crowded.

Pros: Once we hit the coast we skirted down the coas of Florida which provided a spectacular view. The approach and landing at Key West airport was thrilling and absolutely perfect. We’ve flown Delta many times but this was our first but not last time to Key West.
Cons: Nothing

Pros: Cabin crew and captain were great.
Cons: Don't like how you don't get your seat assignment until you get to the gate. I was given the window seat in the very last row for a 6 hour flight, quite uncomfortable. I could've booked another airline for a similar price and picked the seat i wanted at booking. They ran out of food choices by the time they got to the last row, so we were given whatever was left. Delayed because one of the bathroom doors wasn't working, 30 min later still wasn't fixed and ultimately they decided to go without it.

Pros: Staff smooth flight great landing and free movies
Cons: Everything was perfect

Pros: Your entertainment system is fabulous!
Cons: We purchased a direct flight from Boston to Tampa. We paid extra for the convenience of a direct flight Our flight was changed without notification to a connecting flight that was leaving 10 minutes earlier and arriving 2 hours later. Due to malfunction with the kiosk and not a sufficient amount of agents at check in, we missed our flight by 4 minutes. The gate agent seemed to enjoy telling us, with our 10 month old baby, that we were too late. Our baggage, including car seat, had been loaded on the plane. We were reassigned to a flight the following morning. We missed a full day with family, had to travel back home without a car seat and return to the airport the following day. I was shocked and disappointed that not single Delta agent was accommodating or remotely helpful while we were at the airport. I've never had a problem with Delta before. We travel on regularly and would like to continue using Delta. I would like a voucher for my next Delta trip.

Pros: gate staff were great
Cons: plane cabin staff looked overworked

Cons: My wife was told she could not board our flight from Boston to Paris because her passport was expired, even though it was not expired. We were told that in Europe passports cannot expire within 3 months of your departure. However, Delta never let us know about this rule until we literally were boarding the plane. How they could not make us aware of this until we were boarding the airplane is unbelievable and unacceptable. This has ruined our vacation which has been in planning for the last six months.

Pros: Complimentary snack mini-meal. Early departure and arrival. Availability of extra seat and elbow room. Free movies.
Cons: Entertainment screen would not tilt to comfortable angle when passenger in front of me reclined his seat, and the screen/system stopped functioning properly near end of flight.

Pros: Everything was just right

Pros: Delta service and conford are great.
Cons: Pay for wifi


Pros: Im usually not one to sleep on ttransport but I was very comfy on this flight and was able to sleep the whole three hours
Cons: The snacks.

Pros: Nothing
Cons: Everything

Cons: Great flight, ontime departure and early arrival. Bags were delivered within 15 minutes of Ariosto the gate.

Cons: More legroom and monitors in the seat back like Jetblue.

Cons: Feed me

Cons: Too many travelers on the same flight, but I know its the day before thanksgiving so its the way it is.

Pros: Nothing!
Cons: Wifi was not functional, making me unable to do work for the duration of the flight. Rude flight attend literally stormed off mid-conversation as I was asking for assistance with wifi. And this was in FIRST CLASS. Unbelievable. And Unacceptable.

Pros: Crew were exceptional!!! Organizing the passengers and make the arrangements to meet the requirements of social distance. Bravo!!!
Cons: Cookies had a very bad taste. Water was perfect!

Pros: The crew was respectful and friendly, the seat was comfortable

Pros: The comfort of the plane and aircraft crew.
Cons: Customer service. Ridiculous when buying flight tickets, regardless the economy “restriction” if you buy two tickets together you put them together even if your picking the seats. A money scam charging more for us to pick our seats. Common sense isn’t that common

Pros: Lisa Inzerillo is amazing, I don’t know how she kept everyone happy and safe. What an amazing employee she is, please thank her supervisor for such great training and service!
Cons: If Lisa was our flight attendant on previous flights!

Pros: Entertainment was good for the length of the flight.
Cons: Delayed several times, one of which was because they didn’t have enough gas for the trip. The pilot also came in so fast and hard that he slammed on the planes breaks when landing - violently shaking the entire plane.

Cons: Sat on tarmac for over 40 min waiting for gate

Pros: Nothing
Cons: They make flights to depart on time. Also they should tell anything about the reason when they are delaying four times for a flight

Cons: Plane was delayed for 1 hour, electrical problems, which were never fixed. No entertainment no wifi, unable to charge battery on cell phone. Cabin very warm.

Pros: It was on time,!!!

Pros: The crew members were extremely helpful. It was a full flight and hard to find space for all the carry-on luggage, but an extremely helpful stewardess did a great job of finding space for my bag. She was attentive and friendly for the beverage service and really made me feel welcome.

Pros: Crew was nice. Boarding and deplaning was quick. Flight was on time
Cons: WiFi was super slow

Pros: Attentiveness of crew and meeting my needs
Cons: More leg room/space and a FREE sandwich. I’ll take one is those.

Pros: The seat was great
Cons: Cabin crew - service

Pros: Everything
Cons: No idea. I thought everything was good.

Cons: No complaints, great crew, great service, great flight!

Pros: Flight crew were very apologetic
Cons: Missed connecting flight from Miami. Only one flight per day. Had to take a flight to an alternative location, drive for an hour down the coast and take a ferry to my final destination.

Pros: What you expect from an internal US flight: no food, crowded flight, cramped seats. I have come to expect two things - arrive on time and arrive safely. The good, we arrived safely.
Cons: Pulled away from gate and sat on tarmac for over an hour while technical difficulties fixed. We should not have boarded until plane was ready. We arrived over one hour late and just made connecting flight. Our luggage was not so fortunate.

Pros: There was an excellent selection of movies to choose from. The seats were pretty nice and clean and modern. A power outlet at every seat, and not just USB.
Cons: Flight was delayed due to paperwork and some people were racing to their connecting flights. Lots of turbulence. The seats seemed comfortable at first, but actually hurt my tailbone pretty quickly, while the 17 hour flight we took next did not. Tray tables are the folding kind and a bit awkward. We were in the last row by the bathrooms and our seats didn't recline at all. You had to pay for any kind of snacks other than a little bag of pretzels and a package of cookies. We were in one of the last two boarding sections, and the woman letting us on the plane tried to make us check out carry-on luggage, stating that the overhead bins were full. Well, we didn't want to be without our bags for the next 24 hours, so we argued and she let us "try" to bring them on. There was PLENTY of room back there! It's just the standard line they feed, apparently, so beware if you're sitting in the back of the plane!

Cons: No message to call with passengers with kids to board first or any military personnel boarding first.

Pros: Generally clean plane with good entertainment system and technology overall. Diabetic meal much better than in the past.
Cons: Didn't announce meal choices at the start so flight attendant had to repeat herself every. Single. Row. They forgot my diabetic meal on the last part them forgot to include cutlery and it took a long time to sort out but they were otherwise lovely.

Cons: I wish there was another option for a snack. There are many companies that would probably love to advertise through distribution to airline passengers.

Pros: Nice flight, great leg room, staff was friendly and flight was on time.

Pros: Due to a strong tailwind we arrived 45 minutes ahead of schedule. Great service with attentive attendants. However the plane was older than me, no real entertainment system or outlets to plug in smart devices.
Cons: Plane needs to be retired or retrofitted to accommodate smart device charging.

Pros: The terminal seating
Cons: I am a 100% disabled veteran and I was being rushed by flight stewards with no regard to my physical limitations. I wanted to try the kayak route but after this last experience I don’t know if I’ll still with Kayak

Pros: The crew was really nice and caring
Cons: The music and entertainment collection was very limited

Cons: The plane was dirty, the window had a leak, the TV was too far away and the sound system to watch the movie was broken. When the plane is in that poor of a condition, it's time to replace it. F.

Pros: Everything great. Rate food and entertainment moderate because there was no dinner, which we did not require, and we went to sleep so didn't pay attention to entertainment.

Pros: The flight crew was professional, friendly and competent. They served the dinner as early in the flight as possible.
Cons: This was a plane with central screens along the aisle, and the airline chose to broadcast a sci-fi action movie with almost constant flashing blue light, and violent action scenes. This was first of all a movie that many people, including me, would never choose to watch, but since it was on the aisle screens there was no getting away from it. It was also unsuitable for children, even without sound. But mainly, I object to the showing of any film in that situation - only aisle screens available, and on a night flight where most of the passengers are trying to sleep. I was awakened several times by the flashing lights. Other things: one of the bathrooms was not very clean, and the plane felt like the usual cattlecar, with just 3 seats on each side of the aisle, which is unusual and unpleasant for a transatlantic flight.

Cons: I do not like that I am missed my flight and got stuck in a city without any re-embersement. I usually use United, but decided to use American Airlines this time. Sleeping in an airport tonight. Thanks.

Pros: Was on time

Pros: Cabin was clean. Flight attendants were courteous.
Cons: Their snacks were merely a cookie which was okay, but not what I would have wanted.

Cons: After everyone boarded they said they had a 2 hour delay and if you got off the plane your flight would be cancelled. After an hour of sitting on the plane they got everyone off so a different plane could board and take off and then everyone got back on the plane and continued to wait. We left 2.5 hours late and when we arrived at the destination the plane couldn't contact the tower?!?! So we waited another 30 mins...ridiculous, rude, and rather fly southwest

Cons: It was not obvious that I was flying American arlines out of Boston. I was very confy

Pros: The crew were pleasant and friendly. They tried the best that they could given the circumstances.
Cons: My flights were delayed so I missed my connection. I had to fly a red-eye from San Fran to Boston getting in at 6AM with meetings that started at 10AM...had to BUY a day-pass at the Admirals Club (I feel this could have been provided as it was mechanical issues that caused the delays). THEN my trip from Boston home were delayed so they switched me to another flight and then THAT one was delayed twice so I actually got home later than if I had taken the original flight! Overall the flights really sucked!!

Cons: they were keeping delay, delay, and delay when I was on the aircraft. My flight was from BOS to PHL on June 13,2017 was delayed and cancel then they pushed me back. They pushed my flight back on the next morning and without any apologize or responsibilities for me and I have been sleeping in the AIRPORT all night! never go to this airline again! bad and worst airlines ever!!!

Pros: Flight crew somehow noticed that we had someone in our party who could use some extra consideration. They pre boarded us as a result! They were also extra considerate during the flight.

Pros: That I got home safely
Cons: From the get go it was an awful experience ... I travel with an emotional support animal as does my husband because we don't do well with flying. I have anxiety to the max about it & my husband gets ulcerative colitis flare ups any time he's stressed out which is usually while we fly and having our dogs with us turkey makes us feel better. When I called to tell them over the phone we would have our emotional support animal I got an attitude as if I hadn't been doing this for the last 4 years. She reiterated to me that we needed in addition to the letterhead from the doctor a form filled out (which we both did ) . Brought to the airport and sit had to sit at the counter like the girl didn't know what she was doing. Fast forward to finally getting to the gate after being stressed and our flight was delayed. This now only made our 50 min layover in DC 20 min by the time we landed. We ran from one gate to the next hoping we wouldn't miss our flight and when we got there they wouldn't let us on the plane saying things like "your dogs are not on this flight" "there is no documentation" "well then you must not have the right paperwork" ... in front of a bunch of people in line, out of breath, and now embarrassed I am forced to take out my folder and give them all the paperwork I had just given to the customer service desk before our first flight. They let everyone on the plane and still made us stand there and finally said "just go but your dogs aren't on this flight". Fast forward AGAIN to sitting on the flight the flight attendant comes over and says "guys where's you carrier the dogs need to be under the seats" .. we peoceeded again to explain for the seventh time that they were emotional support animals ... she then proceeded "no they are not they are not even listed on this flight" at this point I'm EXTREMLY embarrassed because people on the plane are paying attention and drawing attention to us but not only that ... I have been doing this for years .. I ALWAYS have the proper documentation as does my husband and we have never ran into this kind of disappointment and embarrassment from any airline until now. I was so stressed out to begin with and this deffinately didn't help ... nor did it make us wants to fly on American again. I felt pushed aside, embarrassed, and belittled by multiples employees ... all because the first employee clearly made a mistake and didn't document things correctly ... that should have never been put on us .

Pros: The airplane had screens that tracked the flight progress, which was nice once we finally left.
Cons: The delay leaving Boston caused me major ground transportation problems in Philadelphia. Also boarding agents did a lousy job getting people to check their carry on bags, knowing with a full flight they wouldn't have room. This further delayed take off.

Pros: There's nothing good about AA
Cons: One of the few things SouthWest, Alaska & United did was the proper queuing of people to get into the plane. AA is a free for all - those who follow regulations will fall behind. In this flight from Boston to LAX - I heard there were 80 Priority checking - are you kidding me. Group 1 does not help if I have 80 Priority seating and one family took 12 people in with one elderly. It's good to place Elderly and Military up front first - but to take the Whole entire family - that's not fair - you have 8 able bodies who should be in line with the rest of the crowd. Also who heard of 80 Priority check ins - normally, that's Group 1. Never flying AA unless I a desperate.

Pros: Good experience all around.
Cons: 15 minutes late. No big deal though

Pros: Good crew, very pleasant and professional.
Cons: The three and a half hour delay was not great, but since it was due to weather issues in Chicago, certainly not the airlines fault. However, the communication about the delay was terrible. There was nobody and the gate, so we were relying on automated notifications from the airline. They kept pushing it later by 30 - 45 minutes at a time. We could have gone to the airport much later but just didn't know that.

Cons: The pilots did not show up for my flight after my other connecting flight was delayed and a previous fkight had been cancelled.

Pros: We didn’t crash.
Cons: First class seat was uncomfortable and had very little padding. Meal service was not good. No drinks offered.

Pros: The crew was great as was the check in crew.
Cons: The comfort of the seat and leg space.

Cons: Less people because of COVID

Cons: Fue de lo peor, viaje a Bos a SAL , haciendo escala en NJ , los vuelos súper mega retrasados, pero el más retrasado fue el NJ a SAL , supuestamente iban. A compensar con alimentos pero lo único que dieron fue una galleta vencidas, y una bebida no más mal servicio, no lo recomiendo viajar en UNITED

Cons: I paid $100 for an upgrade on a United which turned out to be the first row, and right beside the rest room (which was erroneously showing as occupied for the first 20 minutes). The traffic made it feel like I was sitting on a bench in Grand Central Station. I chose an aisle seat but ended up mysteriously in the middle seat. I had extra leg room but if I’d eaten the free 5 pretzels I wouldn’t have been able to fit it my seat any longer. The WiFi wasn’t working for the first hour of the flight. The flight attendant got really annoyed when we didn’t look up when he came by with beverages the first time. We all had headphones on and were looking at our personal screens. The activity by the rest room was constant so we didn’t notice it wasn’t just someone waiting for the loo. The luggage took so long to come out I thought my conference would be over before I got it. Overall, I thought it was bad and confirmed why I don’t fly United. Old, dingy planes, poor service. The pilot was pleasant and communicative so there was at least that...

Cons: Serving something substantial to eat would be nice.

Pros: Great take off and landing. My ears were not even plugged up after landing. Great piloting skills by the crew.

Cons: Still in Houston after spending the night. Flight from Boston to SFO WAS DELAYED SEVERAL TIMES and we would have missed our connection to HNL. So we were diverted to IAH, where we spent the night and will leave for HNL soon.

Pros: Non stop . Wife and I were given side by side seats
Cons: Last row

Pros: Professional staff and clean seat with smooth pilot who was not constantly announcing things
Cons: Small seats

Pros: Good. Seating. Not too crowded
Cons: Na

Pros: The flight attendants were so nice, and although our flight was delayed and hour and fifteen minutes and our layover was an hour and fifteen minutes, we were able to make our connection! Since our connection to Portland in Denver was the last flight of the night, they were able to hold it for us. This was wonderful because there weren’t many flights out that weren’t booked solid for the next day. The attendants on this flight were great about updating us with information for the connections and telling us when we would land in Denver.
Cons: The plane was delayed over an hour for cleaning. It was frustrating to say the least.

Pros: The flight was short and sweet. However, the customer service rep checking me in at Logan could have been much more friendly. I was bringing my parents lobster from Maine, and I ended up having to check my box of lobster. I have a United Explorer card and a Chase Sapphire Preferred card and I was juggling my luggage and had to sit my money clip wallet on the counter. Since I had cash in my wallet, the customer service rep abruptly told me, “we don’t accept cash.” I have been flying for most of my life and I know that you have to pay for baggage fees with a credit card. This interaction was disappointing to say the least.
Cons: No beverage service.

Cons: flight was delayed

Pros: A very tall, male, flight attendant very wonderfully took me almost all the way from one end of the horseshoe to the other. I didn't catch his name but he was SO helpful.
Cons: My flight was delayed by a few minutes and by the time we got to San Francisco, boarding was almost done for my connecting flight. I had to literally run from one end of the United terminals to the other... the entire horse shoe.

Pros: Entertainment free and plenty of choices
Cons: Not even any free snacks, seats do not recline much at all

Pros: I loved being in economy plus! The meal was a wonderful surprise and after my tv screen was reset, I enjoyed 2 movies. Nice staff and service.
Cons: Having to go to the back of the plane for the bathroom.

Pros: New plane, great service.
Cons: The hot meal was gross, but that's too be expected these days. It was nice to even get one, honestly. In flight wifi didn't work but the crew was great about helping us get in touch with customer service about it.

Cons: Got re-seated into a non-recline, bulkhead exit row. For a tall guy like me that's a death sentence on a 6h flight that's delayed extra at the end of a day

Cons: Inspire of making it clear all through booking, check-in and seat assignment, I was assigned a seat in an emergency exit. I told crew before I boarded that I could not open the emergency exit at assigned seat, due to an injury. I had to board almost last waiting for them to find someone who would take that seat. Then they put me in a non-reclining seat. I was given the wrong free beverage and the crew never came back. So I had nothing to drink on a 4+ hour long flight.

Pros: Free movies on the plane, because of errors.
Cons: 4 hour delays both ways. We missed our connection flight due to delays on the way home. That connection was the last flight out of that airport home. We ended up having to sleep in the airport overnight, because United wouldn't pay to put us in a hotel even though the delay was because of a mechanical error on the plane. Our 5 hour flight turned into a big ordeal.

Cons: Took 3 days to deliver my case. They have daily flights. Very poor.

Pros: We boarded very quickly. Take off and landing were immediate. I wasn't interrupted as I slept.
Cons: The flight was delayed. Ordinarily, a little over an hour isn't bad, but we ended up landing at 1:30 in the morning, local time. I called United expressing concern about the arrival time when I was first notified of the delay and all I was told was "I'm sorry for the inconvenience." I learned later that there was an earlier flight I could have tried to get on.

Pros: The flight was fine once we were airborne.
Cons: The flight was delayed SEVEN times. After boarding, we sat on the ground another hour. We didn't take off until almost 5 hours after the expected departure. Baggage claim took over 30 minutes, as well, which was exhausting after midnight when we were supposed to get in at 8.

Pros: Seats.
Cons: Sat in the middle of two people who took up part of my seat too.

Pros: I liked the comfort that the plane gave. I also enjoyed the fact that the crew was all very friendly and kind.
Cons: There was no music or free tv to watch on flight. There were delays due to high traffic.

Cons: They had flight delay issues and WE got pushed onto a next day flight but WE had to pay for our hotel when it was their planes delayed!

Pros: Took off late but landed on time
Cons: Packed in like sardines. Hot on board.

Cons: Our plane was constantly moved around prior to boarding and it was 2 hours late.

Cons: 1. Comfort: the headrest on these seats is so uncomfortable! It just props your head forward and causes a lot of neck strain. For most short haul flights, this is not a big deal, but it really makes for an unpleasant journey on the cross-country flights. Also, the four-seat middle section is so poorly designed. There is no way to store personal items under seats without invading the space of your neighbor because the metal frame supporting the row of seats doesn't match with the seats themselves. 2. Entertainment: United could not support continuous streaming of movies/TV shows for every passenger. My movie paused and froze so frequently that I gave up on finishing it and then felt like I had wasted my time. The speed and reliability reminded me of trying to watch movies on a dialup connection. It would be so much better to just have the TV screens built into the seats. All in all, United got a bad batch of planes and should try to take this into consideration when working with Boeing/Airbus on the next order.

Pros: Flash for mac did not install
Cons: I felt like I was on my way to my death

Pros: Ease of boarding and security checking bag at gate
Cons: Check in kiosk couldn't scan phone was glad to unload my carry-on and check it for free. Should be encouraged to check 1 bag for free from start for smaller bags. Flight attendant was crabby when I tried to squeeze past into my seat. She kind of apologized by being nicer to me after that. They kind of yelled at passengers to take their seats to take off. I liked United. Too bad about the incident I read about. I was on a flight with no available seats to LA and thought someone had taken my seat. Turns out I was reading it wirong on my phone abd the last seat available was actually mine.

Cons: Crabby flight attendants

Cons: Still at airport. 40 minute flight delayed 3.5 hours. Now I get home at 2 am.

Pros: The flight was bumpy but otherwise pleasant
Cons: There was a rude passenger that yelled at me as I was exciting the flight suggesting that I cut her off as we were getting off the plane thinking that I took her bag. It was outrageous and completely ruined the flight for me. I realize this has nothing to do with the flight but it just made me feel so crumby and attached that I felt the need to share it. Also the leg room was a joke. We barely had any room to move. I probably won't fly coach on united again due to the bad taste it left in my mouth. Unfortunate because it's hub is in chicago.

Pros: The staff was very friendly and accommodating
Cons: There was some sort of mix up with seat assignments two guys had the same seat assignment. The very nice gentleman who was sitting in my seat due this stood and allowed me to have my seat as it was on the isle and I was in boarding group 5 and my seat was all the way at the end by the bathrooms and needed to be able to stretch my legs into the isle. There was absolutely no leg room what so ever. The dude next to me spent the entire trip jabbing me in the side with his elbow so that he could access what little space I did have. I was unable to move my legs because every two seconds the entire plane was trekking to the back to use the bathroom, because while there was a third bathroom on the plane towards the front, for whatever reason nobody seemed to be using it.

Cons: Because United scheduled flights without regard to airport Construction in Boston my flight was changed 3 times and I still missed my connecting flight. After I missed my flight, they refused to schedule me on the next available flight even though people behind me were scheduled because they were preferred customers. They refused to pay for my hotel and the customer service was rude arrogant and dismissive. I will absolutely never fly United again. The crew on the Boston flight to Newark was lovely everything beyond that was absolutely abhorrent. We got to our connecting flight exactly as boarding closed and they refused to let 11 people board. And subsequently, United staff was rude to us saying it wasn't their fault.

Pros: Once flight began it ran quite smooth
Cons: I chose seats when I booked the tickets. So... Not quite sure how both myself and my partner didn't end up seated together, and both ended up in a middle seat sandwiched between 2 overweight people... Are you little people profiling to break up the overwhelming number of big people? another couple with 2 kids were also broken up into distant areas on the plane. I know everyone complains about so many things, and this wasn't the end of the world, but still, it's not ideal. The seating/etc seemed more disorganized than usual for this flight.

Pros: I was so impressed with the captain and flight attendants handling the engine problems we had that sent us back to the gate for maintenance at Boston. They were calm and professional and (as a fearful flyer) I felt confident the captain was absolutely making sure we were safe to progress.
Cons: It was so hot on the plane!!! It would have been awesome if they would have passed out water.

Pros: The crew was fantastic
Cons: I really didn't like how the TVs were running to make you think you could watch whatever you want but then you had to pay. No one is going to pay for such a short flight, it would be really nice to offer it for free.

Pros: The flight attendants were kind and attentative
Cons: Nothing stood out, no one went above and beyond. When boarding, a flight attendant said there was no room in the overhead for my carry on and told me I had to check in my bag. When I finally boarded the flight, there were many empty spaces that could have fit my carry on

Pros: Except for the boarding process, the flight went smoothly, the crew was friendly and I had no problems.
Cons: The boarding process was confusing. I was issued a boarding pass with "see agent" instead of a seat assignment listed. When I saw the United agent at the gate I was told "don't worry we'll find you a seat." I was confused because I felt that I was treated as if I was flying stand by when in reality I booked my ticket in advance. Everything worked out in the end--I was one of the last on the plane but I got a seat and had no issues with finding a place for my carry-on--however, I prefer having an assigned seat to avoid the anxiety of not knowing what is going on during the boarding process.

Pros: refund
Cons: Hour delay that made me miss my connecting flight. Customer service agent, Theresa, at the United gate was more interested in checking her cell phone text messages & handing out $10 food vouchers than the long of people who have conflicts with connecting flights or missing events in the destination they were flying to. Every minute lost could prevent customers from obtaining another immediate or comparable flight to their destination. Customer service agent sent those who were going to have problems with their connecting flights to the United Airlines service desk, of which, there were no customer service agents at any of the four available stations. I waited 10 minutes for an agent & no one arrived. When I went back to the original line I was standing in, I was forced to go to the back of the line rather than the place I was originally standing. Therefore I waited in line an additional 20-30 minutes. Once I was served they did not have any more seats available on direct flights to Melbourne. They wanted me to fly to NY, then Sydney & then Melbourne. Additionally the customer service agent did not seem confident this flight was not going to have any hiccups. Worst of all, I had been planning this trip for months & it was ruined by United Airlines.

Pros: Crew friendliness
Cons: Boarding was a mess with an adjacent gate exiting at the time of boarding creating a melee of people crossing queues. You have a carry-on baggage policy - stick to it. I wasn't carrying any roll-ons or large items but many of my fellow passengers were carrying multiple items in the hope of either getting them on or having them checked for free. Complete shambles with later boarders running up and down the aisle trying to fit their carry-ons into overhead lockers. Solution: Enforce one item only; Apply free checked items at the gate early. Apply a fee for items that don't fit and were not offered up for checking.

Pros: The flight attendents were attentive and did a great job.
Cons: Customer service was rude to us about our carry on. It was fine on the way to Boston, but made to pay and check it on the way back. other customers had bags our size but we we're rudely told "you need to go pay for your bag that's it". The bag fit effortlessly in the top on the way there.

Pros: On time boarding, nice crew.
Cons: No free food, not a lot of options of free drinks

Pros: The flight was fast and the crew was nice.
Cons: The boarding took forever

Cons: Had to gate check bag both ways. Flight extremely delayed on way home causing me to miss connection; minimal communication from gate crew. A complimentary drink included a Dixie cup full of soda.

Pros: The crew was courteous and nice. Due to a 2+ hour delay we had free movies on the flight.
Cons: The fact that our incoming flight was delayed more than 2 hours.

Pros: Nothing.
Cons: Recently United decided to cancel all of their flights to Denver due to an April snow storm. United was the only company that chose to cancel rather than delay flights. Our flight was cancelled 24 hrs before any snow fell. Their solution was to offer us another flight over 72 hrs out. After spending 6 hrs on the phone with this company (not exaggerating) I feel entitled to say that this company holds zero accountability or concern for their customers. We had to spend an additional $500 to get to our destination last minute through JetBlue.

COVID-19 information

Safety measures for airlines flying from Massachusetts to Florida Keys

Airlines flying from Massachusetts to Florida Keys 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 Massachusetts to Florida Keys

Mandatory masks

Masks required on board, masks provided on flights from Massachusetts to Florida Keys

Social distancing seating

Middle seats unavailable to book on flights from Massachusetts to Florida Keys

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Massachusetts to Florida Keys

Flexible cancellations

Waiving of change fees. Search flexible flights from Massachusetts to Florida Keys

Book cheap flights from Massachusetts to Florida Keys

Recent round-trip flight deals

10/18Mon
nonstopMultiple Airlines
3h 36mBOS-EYW
10/21Thu
1 stopMultiple Airlines
4h 58mEYW-BOS
$144
10/18Mon
nonstopMultiple Airlines
3h 36mBOS-EYW
10/21Thu
2 stopsMultiple Airlines
9h 30mEYW-BOS
$148
10/31Sun
1 stopMultiple Airlines
12h 16mBOS-EYW
11/10Wed
1 stopMultiple Airlines
11h 50mEYW-BOS
$160
10/20Wed
1 stopAmerican Airlines
8h 07mBOS-EYW
10/27Wed
1 stopAmerican Airlines
5h 26mEYW-BOS
$162
11/22Mon
1 stopAmerican Airlines
6h 33mBOS-EYW
11/26Fri
1 stopAmerican Airlines
5h 04mEYW-BOS
$163
1/20Thu
1 stopAmerican Airlines
7h 58mBOS-EYW
1/24Mon
1 stopAmerican Airlines
6h 38mEYW-BOS
$165
10/20Wed
1 stopAmerican Airlines
8h 07mBOS-EYW
10/27Wed
2 stopsAmerican Airlines
11h 38mEYW-BOS
$166
1/16Sun
1 stopAmerican Airlines
5h 40mBOS-EYW
1/21Fri
1 stopAmerican Airlines
7h 21mEYW-BOS
$168
1/17Mon
1 stopAmerican Airlines
8h 14mBOS-EYW
1/20Thu
1 stopAmerican Airlines
7h 52mEYW-BOS
$169
10/13Wed
2 stopsAmerican Airlines
11h 20mBOS-EYW
10/19Tue
2 stopsAmerican Airlines
9h 13mEYW-BOS
$170
1/20Thu
1 stopAmerican Airlines
7h 58mBOS-EYW
1/24Mon
1 stopAmerican Airlines
5h 39mEYW-BOS
$171
10/20Wed
2 stopsAmerican Airlines
8h 05mBOS-EYW
10/27Wed
2 stopsAmerican Airlines
8h 25mEYW-BOS
$172
10/21Thu
1 stopMultiple Airlines
12h 16mBOS-EYW
10/28Thu
1 stopMultiple Airlines
8h 10mEYW-BOS
$179
10/4Mon
1 stopMultiple Airlines
5h 55mBOS-EYW
10/7Thu
1 stopMultiple Airlines
18h 59mEYW-BOS
$189
9/30Thu
nonstopMultiple Airlines
3h 37mBOS-EYW
10/6Wed
1 stopMultiple Airlines
5h 10mEYW-BOS
$191
10/31Sun
2 stopsMultiple Airlines
20h 40mBOS-EYW
11/10Wed
2 stopsMultiple Airlines
28h 14mEYW-BOS
$194
9/30Thu
1 stopDelta
5h 50mBOS-EYW
10/6Wed
1 stopDelta
7h 59mEYW-BOS
$195
10/5Tue
1 stopMultiple Airlines
5h 55mBOS-EYW
10/7Thu
2 stopsMultiple Airlines
37h 35mEYW-BOS
$198
10/23Sat
1 stopJetBlue
6h 12mORH-EYW
10/27Wed
1 stopJetBlue
6h 40mEYW-ORH
$238
10/6Wed
1 stopJetBlue
4h 42mORH-EYW
10/13Wed
1 stopJetBlue
6h 40mEYW-ORH
$319

Search by stops

Search by airline

Search by price

Recent one-way flight deals

9/28Tue
nonstopJetBlue
3h 37mBOS-EYW
$69
9/28Tue
1 stopAmerican Airlines
5h 23mBOS-EYW
$76
9/28Tue
2 stopsAmerican Airlines
7h 21mBOS-EYW
$80
10/20Wed
1 stopAmerican Airlines
8h 07mBOS-EYW
$81
11/10Wed
1 stopAmerican Airlines
7h 36mBOS-EYW
$83
10/26Tue
1 stopAmerican Airlines
5h 22mBOS-EYW
$84
10/20Wed
2 stopsAmerican Airlines
11h 20mBOS-EYW
$85
11/2Tue
1 stopAmerican Airlines
6h 27mBOS-EYW
$86
11/10Wed
2 stopsAmerican Airlines
6h 57mBOS-EYW
$87
10/26Tue
2 stopsAmerican Airlines
8h 50mBOS-EYW
$88
9/30Thu
1 stopMultiple Airlines
24h 32mBOS-EYW
$93
9/30Thu
nonstopJetBlue
3h 37mBOS-EYW
$94
10/3Sun
2 stopsMultiple Airlines
26h 47mBOS-EYW
$100
10/14Thu
1 stopMultiple Airlines
24h 17mBOS-EYW
$101
10/19Tue
nonstopJetBlue
3h 36mBOS-EYW
$114
10/1Fri
1 stopUnited Airlines
9h 10mBOS-EYW
$118
10/12Tue
nonstopJetBlue
3h 36mBOS-EYW
$124
10/12Tue
3 stopsMultiple Airlines
38h 17mBOS-EYW
$131
1/15Sat
1 stopUnited Airlines
23h 30mBOS-EYW
$137
1/15Sat
2 stopsUnited Airlines
23h 55mBOS-EYW
$142

Search by stops

Search by airline

Search by price

Flights to Florida Keys

Return flight deals:

Florida Keys - Massachusetts

Cabin classes:

$212
$212
$132
$31

Browse destinations: