BOS

$94 Find Cheap Flights from Florida Keys to Boston

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Boston departing on 9/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Florida Keys to Boston

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Florida Keys to Boston that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Florida Keys to Boston

Thu, Jul 16 - Mon, Jul 20
Delta Logo
6:18 pm - 1:20 am
EYW
-
BOS
7h 02m
1 stop
Delta Logo
5:30 am - 11:00 am
BOS
-
EYW
5h 30m
1 stop
$187Delta
Tue, Aug 18 - Sat, Aug 22
Delta Logo
7:58 pm - 11:36 pm
MIA
-
BOS
3h 38mnonstop
Delta Logo
6:05 am - 2:21 pm
BOS
-
MIA
8h 16m
1 stop
$218Delta
Thu, Aug 20 - Tue, Aug 25
Delta Logo
7:58 pm - 11:36 pm
MIA
-
BOS
3h 38mnonstop
Delta Logo
7:20 am - 10:52 am
BOS
-
MIA
3h 32mnonstop
$222Delta
Thu, Aug 20 - Sat, Aug 22
Southwest Logo
11:45 am - 10:20 pm
MIA
-
BOS
10h 35m
1 stop
Southwest Logo
5:30 am - 1:55 pm
BOS
-
MIA
8h 25m
1 stop
$223Southwest
Wed, Jun 24 - Tue, Jun 30
Frontier Logo
5:26 pm - 1:27 am
MIA
-
BOS
8h 01m
1 stop
Frontier Logo
6:00 am - 4:31 pm
BOS
-
MIA
10h 31m
1 stop
$225Frontier
Thu, Aug 27 - Thu, Sep 10
American Airlines Logo
8:05 pm - 11:26 pm
MIA
-
BOS
3h 21mnonstop
American Airlines Logo
5:00 am - 8:28 am
BOS
-
MIA
3h 28mnonstop
$227American Airlines
Thu, Aug 20 - Mon, Aug 24
Southwest Logo
11:45 am - 10:20 pm
MIA
-
BOS
10h 35m
1 stop
Southwest Logo
5:25 am - 11:50 am
BOS
-
MIA
6h 25m
1 stop
$228Southwest
Thu, Aug 27 - Wed, Sep 2
Southwest Logo
5:05 pm - 10:10 pm
MIA
-
BOS
5h 05m
1 stop
Southwest Logo
2:10 pm - 8:10 pm
BOS
-
MIA
6h 00m
1 stop
$229Southwest
Sat, Sep 5 - Tue, Sep 8
American Airlines Logo
5:55 pm - 9:30 pm
MIA
-
BOS
3h 35mnonstop
American Airlines Logo
7:22 pm - 12:48 am
BOS
-
MIA
5h 26m
1 stop
$232American Airlines
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
3:57 pm - 1:14 am
MIA
-
BOS
9h 17m
1 stop
United Airlines Logo
6:00 pm - 11:52 pm
BOS
-
MIA
5h 52m
1 stop
$236United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$94
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Key West to Boston

FAQs for booking flights from Florida Keys to Boston

  • How does KAYAK find such low prices on flights from Florida Keys to Boston?

    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 Florida Keys to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Florida Keys 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 Florida Keys to Boston?

    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 Boston with an airline and back to Florida Keys with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida Keys to Boston?

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

Reviews of the top 5 airlines serving from Florida Keys to Boston

 
Need help choosing which airline to fly with from Florida Keys to Boston? 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.
7.9
DeltaOverall score based on 8394 reviews
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
7.8Comfort
Airline reviews

Five hour delays every hour, I wish it were all at once

2.0 MediocreAnonymous, Jun 2026
MCO - LGA
Read more Delta reviews

Five hour delays every hour, I wish it were all at once

Got rerouted from a straight flight from Orlando to Atlanta to Knoxville to a flight from Orlando to Detroit to Knoxville! Seriously!! Flight delay out of Detroit! Long day for what should have been a pretty easy travel day!

If you cant travel Delta One, Comfort Class is the next best thing!

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Clean planes and not take my comfort class seat away.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Aside from a completely packed plane, I really have no complaints.

I missed my flight and had to buy new tickets Rome- Boston

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

The flight had a delay but I made it to my connection. Flight was smooth overall

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

Super friendly with lots of drink options an entertainment. Friendly crew.

Flights were on time actually early service was good and crew cheerful

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

Flights were on time. Free Wifi on plane. Everything was well organized.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Very hard to beat a British Airways international flight…the crews are always so amazing! One flight attendant that really stood out was Emma…she was very personable and accommodating with any request we had!!

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was extremely slow and disorganized. Onboard crew was unfriendly.

There was a screen but no earphones that could use the older input so I could listen to anything.

Jet blue just had great service overall! Only a little turbulence heading out of Austin, otherwise the jet stream helped the speed of the trip!

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Boarding was fast, easy, and we landed early. The entertainment system was very buggy and kept resetting throughout the flight.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

It was an early flight and most people napped/slept and the crew let us which was nice.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

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