EYW - BOS

$116 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 11/6. 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.
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Everything you should know

Cheapest round-trip
$277
Typical prices: $239-$421
American Airlines
Wed 8/26Mon 8/31
EYW - BOS • 1 stop
Cheapest non-stop
$364
JetBlue
Thu 10/8Mon 10/12
EYW - BOS • Non-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
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Nonstop flights
Mon, Thu, Fri, Sat, Sun
You can fly direct with JetBlue. Average duration is 0
Direct flights
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Top airlines
Cheapest • from $277 (round-trip)
Best reviews • 7.8 score
Airline reviews
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Airline reviews
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Top layover airports
Cheapest • Avg $209 (round-trip)
Shortest trip • 5h 25m (one-way)
Insights
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Insights
When to travel
Cheapest • 31% price drop
Most popular
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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

Wed, Aug 26 - Mon, Aug 31
American Airlines Logo
1:50 pm - 7:14 pmEYW  Key West-BOS Boston Logan Intl
5h 24m1 stop Charlotte Douglas
American Airlines Logo
6:06 am - 1:05 pmBOS  Boston Logan Intl-EYW Key West
6h 59m1 stop Miami
$277American Airlines
Tue, Dec 22 - Tue, Dec 29
American Airlines Logo
7:52 pm - 12:59 amEYW  Key West-BOS Boston Logan Intl
5h 07m1 stop Miami
American Airlines Logo
5:50 am - 1:47 pmBOS  Boston Logan Intl-EYW Key West
7h 57m1 stop Philadelphia
$277American Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
1:43 pm - 9:58 pmEYW  Key West-BOS Boston Logan Intl
8h 15m1 stop Miami
American Airlines Logo
6:00 am - 1:30 pmBOS  Boston Logan Intl-EYW Key West
7h 30m1 stop Washington, D.C. Reagan-National
$277American Airlines
Tue, Sep 1 - Sun, Sep 13
Multiple Airlines Logo
1:14 pm - 11:50 amEYW  Key West-BOS Boston Logan Intl
46h 36m2 stops Tampa Raleigh-Durham
Multiple Airlines Logo
11:53 am - 10:19 amBOS  Boston Logan Intl-EYW Key West
22h 26m1 stop Orlando
$336Multiple Airlines
Tue, Sep 1 - Sun, Sep 13
Delta Logo
6:15 pm - 1:25 amEYW  Key West-BOS Boston Logan Intl
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
5:30 am - 10:46 amBOS  Boston Logan Intl-EYW Key West
5h 16m1 stop Atlanta Hartsfield-Jackson
$347Delta
Thu, Oct 8 - Mon, Oct 12
JetBlue Logo
12:50 pm - 4:39 pmEYW  Key West-BOS Boston Logan Intl
3h 49mnonstop
JetBlue Logo
8:00 am - 11:59 amBOS  Boston Logan Intl-EYW Key West
3h 59mnonstop
$364JetBlue
Fri, Aug 28 - Sun, Aug 30
Multiple Airlines Logo
12:07 pm - 9:09 amEYW  Key West-BOS Boston Logan Intl
21h 02m1 stop Orlando
Multiple Airlines Logo
12:45 pm - 12:31 pmBOS  Boston Logan Intl-EYW Key West
23h 46m2 stops Atlanta Hartsfield-Jackson Tampa
$369Multiple Airlines
Thu, Oct 29 - Sat, Oct 31
Allegiant Air Logo
2:43 pm - 9:11 amEYW  Key West-BOS Boston Logan Intl
18h 28m1 stop Asheville Regional
Allegiant Air Logo
9:02 am - 9:22 amBOS  Boston Logan Intl-EYW Key West
24h 20m2 stops Knoxville McGhee Tyson Tampa St. Petersburg
$372Allegiant Air
Thu, Oct 29 - Mon, Nov 2
JetBlue Logo
12:45 pm - 4:15 pmEYW  Key West-BOS Boston Logan Intl
3h 30mnonstop
JetBlue Logo
8:00 am - 11:53 amBOS  Boston Logan Intl-EYW Key West
3h 53mnonstop
$489JetBlue
Mon, Aug 17 - Wed, Aug 19
Delta Logo
6:15 pm - 1:25 amEYW  Key West-BOS Boston Logan Intl
7h 10m1 stop Atlanta Hartsfield-Jackson
Delta Logo
8:55 am - 5:20 pmBOS  Boston Logan Intl-EYW Key West
8h 25m1 stop Atlanta Hartsfield-Jackson
$522Delta
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.

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 Sunday 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 November, where tickets cost $286 (return) on average. On the other hand, the most expensive months are April and September, where the average cost of round-trip tickets is $627 and $601 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 $548 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 season

March

Cheapest flight

$116
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly and prices are also 7% 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 $115 for a one-way ticket and $277 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 $382 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 $384 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.

Prefer to fly direct from Key West to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Key West to Boston Logan Intl.
Find which airlines fly direct from Key West Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Key West to Boston Logan Intl

Monday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

Direct returns

Boston Logan Intl to Key West

Monday

JetBlue

JetBlue

Thursday

JetBlue

JetBlue

Friday

JetBlue

JetBlue

Saturday

JetBlue

JetBlue

Sunday

JetBlue

JetBlue

See more direct flights

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 8492 reviews
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
7.8Comfort
Airline reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

4.0 OkayNoel, Aug 2026
Read more Delta reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

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.

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.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

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.

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.

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