EYW - BOS

$117 Find Cheap Flights from Key West 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 from Key West to Boston departing on 5/22. 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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$227
Typical prices: $417-$369
Delta
Wed 5/6Sun 5/10
EYW - BOS • 1 stop
Cheapest one-way
$117
Typical prices: $223-$417
Allegiant Air
Fri 5/22
EYW - BOS • 1 stop
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
JetBlue’s Blue Basic offers carry-on and live TV.
Arrive two hours early at EYW for security lines.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $227 (round-trip)
Best reviews • 7.2 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $231 (round-trip)
Shortest trip • 5h 13m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
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

Wed, May 6 - Sun, May 10
Delta Logo
6:23 pm - 1:15 am
EYW
-
BOS
6h 52m
1 stop
Delta Logo
7:00 am - 1:42 pm
BOS
-
EYW
6h 42m
1 stop
$227Delta
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
11:46 am - 1:24 am
EYW
-
BOS
13h 38m
2 stops
Multiple Airlines Logo
9:36 am - 10:11 am
BOS
-
EYW
24h 35m
1 stop
$250Multiple Airlines
Wed, May 6 - Sun, May 10
Multiple Airlines Logo
11:46 am - 1:24 am
EYW
-
BOS
13h 38m
2 stops
Multiple Airlines Logo
7:00 am - 11:27 am
BOS
-
EYW
28h 27m
1 stop
$262Multiple Airlines
Tue, May 5 - Sat, May 9
Delta Logo
6:23 pm - 1:15 am
EYW
-
BOS
6h 52m
1 stop
Delta Logo
9:10 am - 5:23 pm
BOS
-
EYW
8h 13m
1 stop
$287Delta
Mon, May 11 - Wed, May 13
Multiple Airlines Logo
11:01 am - 9:12 am
EYW
-
BOS
22h 11m
2 stops
Multiple Airlines Logo
10:07 am - 1:07 pm
BOS
-
EYW
27h 00m
1 stop
$289Multiple Airlines
Tue, Sep 1 - Sat, Sep 12
Multiple Airlines Logo
1:14 pm - 11:54 pm
EYW
-
BOS
34h 40m
2 stops
Multiple Airlines Logo
3:56 pm - 10:19 am
BOS
-
EYW
18h 23m
1 stop
$299Multiple Airlines
Mon, May 11 - Wed, May 13
Multiple Airlines Logo
12:07 pm - 9:12 am
EYW
-
BOS
21h 05m
1 stop
Multiple Airlines Logo
10:07 am - 1:07 pm
BOS
-
EYW
27h 00m
1 stop
$303Multiple Airlines
Fri, May 22 - Mon, May 25
Multiple Airlines Logo
12:07 pm - 9:42 pm
EYW
-
BOS
9h 35m
1 stop
Multiple Airlines Logo
5:45 am - 12:34 pm
BOS
-
EYW
30h 49m
2 stops
$304Multiple Airlines
Thu, Jun 4 - Mon, Jun 8
Multiple Airlines Logo
12:05 pm - 9:42 pm
EYW
-
BOS
9h 37m
1 stop
Multiple Airlines Logo
5:45 am - 12:34 pm
BOS
-
EYW
30h 49m
2 stops
$305Multiple Airlines
Thu, Jul 30 - Mon, Aug 3
American Airlines Logo
5:35 pm - 11:49 pm
EYW
-
BOS
6h 14m
1 stop
American Airlines Logo
10:12 am - 6:47 pm
BOS
-
EYW
8h 35m
1 stop
$307American 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 May.

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 November, where tickets cost $301 (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 $609 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 $591 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$117
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 3% 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 3 days, the lowest price for a flight from Key West to Boston was $117 for a one-way ticket and $227 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?

    oneworld is the only airline alliance operating flights between Key West and Boston.

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

    The two airlines most popular with KAYAK users for flights from Key West to Boston are JetBlue and American Airlines. With an average price for the route of $476 and an overall rating of 7.2, JetBlue is the most popular choice. American Airlines is also a great choice for the route, with an average price of $363 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.

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

  • Looking for a cheap flight? 25% of our users found flights on this route for $256 or less one-way and $627 or less round-trip.

Reviews of the top airlines flying 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.
7.2
JetBlueOverall score based on 2951 reviews
7.2Entertainment
6.6Food
7.9Crew
7.5Comfort
7.3Boarding
Airline reviews

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!

2.0 MediocreAmy, Apr 2026
MCO - BOS
Read more JetBlue reviews

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!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

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

Entertainment and wifi were very sub-par - audio issues and no wifi

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

Still hasn’t left. Why are you asking how it was?

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

For the price point it was very good. Definitely leave on the earlier flights as it can become terribly crowded later in the day

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.

Business class was very good, one of my best flights

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.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the 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 —

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

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

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