EYW - BOS

$129 Find Cheap Flights from Key West to Boston - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Boston departing on 11/2. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Boston, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Boston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$267
Typical prices: $336-$893
Multiple Airlines
Fri 9/11Sun 9/13
EYW - BOS • 1 stop
Cheapest one-way
$129
Typical prices: $177-$404
Allegiant Air
Mon 11/2
EYW - BOS • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue Blue Basic adds a carry-on and Wi-Fi; American Basic Economy boards later.
American Main Cabin Extra adds early boarding and drinks on this longer flight.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $327 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $231 (round-trip)
Shortest trip • 5h 22m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 26% price drop
Most popular
Good to know
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+1
+1
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Flight Deals
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Expert advice
Flight Deals

Cheap Flights from Key West to Boston (EYW-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West 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 Key West to Boston

Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
10:59 am - 10:09 am
EYW
-
BOS
23h 10m
1 stop
Multiple Airlines Logo
11:05 am - 10:19 am
BOS
-
EYW
23h 14m
1 stop
$267Multiple Airlines
Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
10:59 am - 10:09 am
EYW
-
BOS
23h 10m
1 stop
Multiple Airlines Logo
11:28 am - 12:19 pm
BOS
-
EYW
24h 51m
2 stops
$297Multiple Airlines
Fri, Aug 14 - Sat, Aug 22
Multiple Airlines Logo
10:31 am - 9:05 am
EYW
-
BOS
22h 34m
1 stop
Multiple Airlines Logo
12:45 pm - 7:13 pm
BOS
-
EYW
30h 28m
2 stops
$299Multiple Airlines
Tue, Jul 14 - Thu, Jul 16
Multiple Airlines Logo
1:14 pm - 7:46 am
EYW
-
BOS
18h 32m
2 stops
Multiple Airlines Logo
10:04 am - 11:27 am
BOS
-
EYW
25h 23m
1 stop
$314Multiple Airlines
Mon, Jul 13 - Sat, Jul 18
Multiple Airlines Logo
12:07 pm - 9:09 am
EYW
-
BOS
21h 02m
1 stop
Multiple Airlines Logo
8:37 am - 10:24 am
BOS
-
EYW
25h 47m
2 stops
$323Multiple Airlines
Tue, Jul 21 - Tue, Aug 18
American Airlines Logo
7:40 pm - 12:59 am
EYW
-
BOS
5h 19m
1 stop
American Airlines Logo
5:35 am - 1:09 pm
BOS
-
EYW
7h 34m
1 stop
$327American Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
12:05 pm - 9:09 am
EYW
-
BOS
21h 04m
1 stop
Multiple Airlines Logo
12:45 pm - 12:34 pm
BOS
-
EYW
23h 49m
2 stops
$332Multiple Airlines
Thu, Jul 9 - Wed, Jul 15
Delta Logo
6:18 pm - 1:20 am
EYW
-
BOS
7h 02m
1 stop
Delta Logo
6:45 am - 1:23 pm
BOS
-
EYW
6h 38m
1 stop
$342Delta
Fri, Jul 24 - Tue, Jul 28
United Airlines Logo
2:26 pm - 9:53 pm
EYW
-
BOS
7h 27m
1 stop
United Airlines Logo
5:45 am - 3:19 pm
BOS
-
EYW
9h 34m
2 stops
$346United Airlines
Mon, Jul 13 - Thu, Jul 16
American Airlines Logo
5:34 pm - 11:49 pm
EYW
-
BOS
6h 15m
1 stop
American Airlines Logo
10:56 am - 7:06 pm
BOS
-
EYW
8h 10m
1 stop
$347American Airlines
Booking Insights

KAYAK's insights & trends for Key West to Boston flights

Get data-powered insights and trends into flights from Key West to Boston to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Key West to Boston?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Key West to Boston departing in September.

What’s the cheapest day of the week to fly from Key West to Boston?

The average price of all round-trip flights from Key West to Boston clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Boston on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Key West to Boston. For your return ticket, we recommend flying on a Monday and avoiding Thursdays for the best deals.

What is the cheapest month to fly from Key West to Boston?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Boston, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Key West to Boston is August, where tickets cost $316 (return) on average. On the other hand, the most expensive months are September and April, where the average cost of round-trip tickets is $882 and $627 respectively.

Can I save money by flying with a layover from Key West to Boston?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $383 on average.

Expert advice

Expert advice for your flight from Key West to Boston

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines and JetBlue

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Paul Rubio

Paul Rubio

Expert on EYW

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Blane Bachelor

Blane Bachelor

Expert on BOS

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Good to know

Low seasonMarch
Cheapest flight$129
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Key West to Boston

When to book flights from Key West to Boston

Are your dates flexible? Find out the best times to travel from Key West to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Key West to Boston

  • What is the cheapest flight from Key West to Boston?

    In the last 5 days, the lowest price for a flight from Key West to Boston was $129 for a one-way ticket and $267 for a round-trip.

  • Do I need a passport to fly between Key West and Boston?

    A passport is not required to fly from Key West to Boston.

  • Which airports will I be using when flying from Key West to Boston?

    On your way to Boston, you’ll fly out from Key West. You’ll be landing at Boston Logan Intl.

  • Which airlines offer Wi-Fi service onboard planes from Key West to Boston?

    JetBlue, and American Airlines offer inflight Wi-Fi service on the Key West to Boston flight route.

  • Which aircraft models fly most regularly from Key West to Boston?

    The Airbus A220-300 is the aircraft model that flies most regularly on the Key West to Boston flight route.

  • Which airline alliances offer flights from Key West to Boston?

    SkyTeam, and oneworld are the airline alliances operating flights between Key West and Boston, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Key West to Boston, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from Key West to Boston are Delta and American Airlines. With an average price for the route of $343 and an overall rating of 7.8, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $365 and an overall rating of 7.1.

  • How does KAYAK find such low prices on flights from Key West 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 Key West to Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Key West 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 Key West 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 Key West with another airline. Booking your flights between Key West and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West 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 Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Key West to Boston

 
See real verified KAYAK customer reviews for airlines flying from Key West to Boston. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West 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.
7.8
DeltaOverall score based on 8452 reviews
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
7.8Comfort
Airline reviews

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

2.0 MediocreBlake, Jun 2026
SEA - BOS
Read more Delta reviews

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

The tray table was broken and the food was terrible.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

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

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

The boarding agents appeared to do the minimum customer service. They did not appear to try to find solutions to problems.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Half of the TSA checkpoints at PHL are closed. Also, there is no standby for first class passengers. You can only standby for coach. Very dated policy and inconsistent with peers.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

I had a horrible experience from the time I dropped off my bags until the time I landed. The staff taking the bags at the check-in counter prior to security, forced me to check my baby stroller, even though it weighed less than 20 pounds. their excuse was that the wheels were too big. I have never had an issue gate checking this exact same stroller in the past either on American or on any other airline. when I asked for the agent to show me the rule about the size of the wheels on strollers, they told me to look it up on the AA website. I did so, and did not find any indication that wheel size was a problem for gate checking strollers. The only limitation would be the weight of the stroller which mine was below. I was left with a one-year-old child and all of my carry-on luggage, diaper bag, and the like to walk around the airport without the assistance of a stroller and had the same issue when I exited the plane and had to go all the way to baggage claim without a stroller. In addition, while on the airplane, I was told I can only get one bag of cookies as a snack, even though I was with a child. Apparently my child and I were supposed to share a cookie. While this latter issue is a minor one, it is just another example of the absolutely horrible customer service that American Airlines provides. In addition, the 737 aircraft that I was on was extremely hot and the air vents above the seat were so far away from the aisle and middle seats that it was comical. I could barely reach the air vent to adjust it. I had to ask the person in the window seat to do it for me. The whole experience was just a nightmare.

The flight was on time and everything went very smoothly.

Free WiFi and movies were not free - everything required signing up for future billing. Boston bound crew were very courteous and gracious.

This flight was intense. It was overcrowded, people weren’t following Covid guidelines. And in general, was a mess due to young kids causing a lot of noise and disturbance. I ended up with a headache the entire flight because of it.

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.

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!

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

very difficult boarding process - aggressive passengers not the friendliest crew

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Everything you need to know for your flight from Key West to Boston

Information on your arrival and departure airports