BOS - EYW

$99 Find Cheap Flights from Boston to Key West

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Key West departing on 5/20. 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 Key West

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

Cheapest round-trip
$334
Typical prices: $482-$352
Multiple Airlines
mié. 5/6lun. 5/11
BOS - EYW • 1 stop
Cheapest non-stop
$869
JetBlue
sáb. 4/25lun. 4/27
BOS - EYW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue's free Wi-Fi and live TV enhance in-flight comfort.
EYW is a ten-minute drive to Key West's Old Town.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $337 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $314 (round-trip)
Shortest trip • 5h 44m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% price drop
Most popular
Good to know
Good to know
+1
+1
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Flight Deals
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Flight Deals

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

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

mié., may. 6 - lun., may. 11
Multiple Airlines Logo
10:07 am - 11:25 am
BOS
-
EYW
25h 18m
1 stop
Multiple Airlines Logo
12:07 pm - 9:12 am
EYW
-
BOS
21h 05m
1 stop
$334Multiple Airlines
mié., may. 6 - lun., may. 11
Multiple Airlines Logo
10:07 am - 11:25 am
BOS
-
EYW
25h 18m
1 stop
Multiple Airlines Logo
1:11 pm - 1:24 am
EYW
-
BOS
36h 13m
2 stops
$335Multiple Airlines
sáb., may. 2 - mar., may. 5
Delta Logo
9:30 am - 5:23 pm
BOS
-
EYW
7h 53m
1 stop
Delta Logo
6:23 pm - 1:15 am
EYW
-
BOS
6h 52m
1 stop
$337Delta
lun., may. 25 - jue., may. 28
American Airlines Logo
10:52 am - 7:10 pm
BOS
-
EYW
8h 18m
2 stops
American Airlines Logo
7:40 pm - 12:59 am
EYW
-
BOS
5h 19m
1 stop
$338American Airlines
mié., may. 6 - lun., may. 11
Multiple Airlines Logo
9:20 am - 11:25 am
BOS
-
EYW
26h 05m
1 stop
Multiple Airlines Logo
11:07 am - 1:24 am
EYW
-
BOS
38h 17m
2 stops
$339Multiple Airlines
jue., may. 14 - lun., may. 18
Multiple Airlines Logo
10:07 am - 11:27 am
BOS
-
EYW
25h 20m
1 stop
Multiple Airlines Logo
1:11 pm - 8:44 am
EYW
-
BOS
19h 33m
2 stops
$340Multiple Airlines
mié., may. 20 - dom., may. 24
Multiple Airlines Logo
12:01 pm - 11:25 am
BOS
-
EYW
23h 24m
2 stops
Multiple Airlines Logo
10:55 am - 8:39 am
EYW
-
BOS
21h 44m
1 stop
$341Multiple Airlines
dom., jul. 19 - vie., jul. 24
American Airlines Logo
8:19 am - 5:13 pm
BOS
-
EYW
8h 54m
1 stop
American Airlines Logo
1:38 pm - 9:33 pm
EYW
-
BOS
7h 55m
2 stops
$342American Airlines
mié., may. 27 - mié., jun. 3
American Airlines Logo
10:47 am - 6:49 pm
BOS
-
EYW
8h 02m
2 stops
American Airlines Logo
1:39 pm - 10:35 pm
EYW
-
BOS
8h 56m
2 stops
$343American Airlines
sáb., may. 2 - sáb., may. 9
Multiple Airlines Logo
11:16 am - 9:06 am
BOS
-
EYW
21h 50m
1 stop
Multiple Airlines Logo
11:54 am - 8:44 am
EYW
-
BOS
20h 50m
2 stops
$344Multiple Airlines
Booking Insights

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

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

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

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

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston to Key West, 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 Boston to Key West is September, where tickets cost $316 (return) on average. On the other hand, the most expensive months are April and March, where the average cost of round-trip tickets is $602 and $505 respectively.

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

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 $527 on average.

How far in advance should I book a flight from Boston to Key West?

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

To get a below average price on the flight from Boston to Key West, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Expert advice

Expert advice for your flight from Boston to Key West

 
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 seasonAugust
Cheapest flight$99
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Boston to Key West

When to book flights from Boston to Key West

Are your dates flexible? Find out the best times to travel from Boston to Key West 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 Boston to Key West

  • How early should I be to BOS when I’m scheduled to travel?

    On the date you’re set to travel, you should reach BOS at least 1h 30min before your flight is scheduled to take off. Getting to this airport an hour early will enable you clear the airport’s lengthy security lines in time for your flight.

  • Where should I park my car at BOS?

    If you drive to BOS, there are several on-site and off-site parking garages you can leave your car at. You should park your car at one of the airport’s off-site parking garages, as these garages charge cheaper rates than the on-site ones.

  • What is the best way to travel from EYW to Key West?

    To travel from EYW to Key West, you can catch a bus or a taxi. If you’d like to travel quickly, you should board one of the taxis that ply this route, whereas if you’d like to travel affordably, you should board a bus. It’s worth noting that although it is a bit more expensive than traveling by bus, traveling by taxi is more appropriate because if you use one, you’ll be dropped out right at the doorstep of your destination of choice.

  • Does EYW have an on-site hotel?

    Key West International Airport has no on-site hotel. However, if you’d like to stay near it, there are various hotels you should consider. They include Hampton Inn Key West, Margaritaville Beach House Key West, and DoubleTree by Hilton Hotel Grand Key Resort.

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

    In the last 3 days, the lowest price for a flight from Boston to Key West was $99 for a one-way ticket and $334 for a round-trip.

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

    No

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

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

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

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

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

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

  • What is the most popular layover when flying to Key West from Boston?

    Charlotte is the most popular layover city among KAYAK users traveling from Boston to Key West.

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

    The two airlines most popular with KAYAK users for flights from Boston to Key West are Delta and United Airlines. With an average price for the route of $396 and an overall rating of 7.9, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $324 and an overall rating of 7.4.

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

    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 Boston to Key West.

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

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

    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 Key West with an airline and back to Boston with another airline. Booking your flights between Boston and EYW 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 Boston to Key West?

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

KAYAK’s top tips for finding a cheap flight from Boston to Key West

  • Looking for a cheap flight? 25% of our users found flights on this route for $203 or less one-way and $462 or less round-trip.
  • TSA Care offers special assistance services at Boston Logan International Airport (BOS). If you’d like to receive any of the special assistance services it offers, you should contact its BOS office and inform the representative you’ll talk to of the type of assistance you’ll need at least 72h before your flight.
  • If you’re an active military member or a dependent of one, you can access the USO Lounge at BOS for free. Situated in Terminal C, a short distance from the American Airlines Credit Union, this lounge features comfortable seats, reading material, clean lavatories, snacks, and fast internet.
  • Classique Salon offers top-notch hair and nail services at BOS. Located in Terminal C, this establishment, open from 7:30 am to 6 pm. on Mondays to Fridays and 8 am to 5 pm on Saturdays, has several well-trained and experienced hair and nail stylists. Thus, you can count on receiving nothing short of elite services at this salon.
  • In Key West, you’ll alight from your flight at Key West International Airport (EYW). If you need to withdraw some cash before leaving, you can do so with ease, as EYW has several operational ATMs. They are located in the airport’s Ticketing Area, departure lounge, and baggage claim area.
  • If you’re traveling with an infant, you can breastfeed him/her without the glaring eyes of the public, as EYW features a Mamava Suite in its Departure Lounge. To access this Mamava suite, all you have to do is inform one of the airport staff, and they will assist you accordingly.

Reviews of the top 5 airlines serving from Boston to Key West

 
See real verified KAYAK customer reviews for airlines flying from Boston to Key West. 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 Boston to Key West? 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 8438 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

6.0 GoodAkanksha Devidas, Apr 2026
BOS - JFK
Read more Delta reviews

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

N Everything was perfect from boarding to assistance to baggage in Tampa

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

The whole experience was excellent. As it most often is with Delta

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

It’s always a great time flying with united airlines.

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

I couldn’t make my first flight due to weather delays trapping us in the town we were in. Then I had to buy a new ticket

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Much better than Spirit. I was please by the easy fast check in and boarding

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Both flights were significantly delayed. The flight experience itself was great.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Flight left early and arrived 30 MINUTES early at the destination. Smooth trip.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

Very disappointing. Flight was delayed by 1.5 hours and food options are very underwhelming even for first class seats (same food given to economy seats)

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Incoming flight was delayed, delaying boarding. It then took 30 mins to take off. Took 20 mins to get to a gate because they changed the gate last minute, crew weren’t ready so there was no one staffed to work the jet bridge. Boarding was so disorganized as is usual with American because everyone just stands around the gate regardless of boarding group.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

Flight was delayed 6plus hours Did not take flight Customer service was terrible Will never fly again and will spread how terrible you are You stink

I didnt have a flight. Kayak must be on drugs because I confirmed with spirit that I had no booked flight.

We were surprised to be charged $99 for a personal item. And of course everything offered on the flight was an additional charge. Other than that the pilot flew and landed the plane well and the attendants and fellow passengers were nice enough.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

The repeated flight delays—this time nearly three hours without any weather-related cause—are unacceptable. Yet, passengers are penalized heavily even for being a minute late. It is unreasonable that there is no compensation for such significant delays, nor even basic provisions like water during the wait or in flight. This imbalance in accountability is deeply frustrating and needs to be addressed.

Always Good ,… Spirit customers are high class Delta customers are self proclaimed elites and American crews you can hear them complain about everything (they’re loud)

They cancelled my flight with no reason affecting my travel plans and delaying it 24 hours.

Everything was horrible. They delayed my flight so I missed my connection flight and I lost my bags. I had to go to the same workers multiple times asking the same questions because everyone kept giving me different answers. One person closed down customer service because he wanted to go on lunch so there was like 30 people just waiting for hours because no one would relieve him.

Landing was technically perfect. What I didn't like is the pricey internet. Both flights with excellent crews. I'm 6 feet 210 pounds and could easily fit in the chair.

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

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

Information on your arrival and departure airports