$93 Find Cheap Flights from Key West to Massachusetts

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 Massachusetts departing on 8/31. 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 Massachusetts

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Massachusetts, 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 Massachusetts, as well as popular online travel agencies
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Flight Deals

Book Cheap Key West to Massachusetts Plane Tickets

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

Thu, May 28 - Wed, Jun 3
American Airlines Logo
7:40 pm - 12:59 am
EYW
-
BOS
5h 19m
1 stop
American Airlines Logo
8:00 am - 1:41 pm
BOS
-
EYW
5h 41m
1 stop
$197American Airlines
Fri, May 22 - Mon, May 25
American Airlines Logo
5:37 pm - 11:49 pm
EYW
-
BOS
6h 12m
1 stop
American Airlines Logo
6:00 am - 12:16 pm
BOS
-
EYW
6h 16m
1 stop
$262American Airlines
Thu, May 21 - Tue, May 26
United Airlines Logo
3:55 pm - 1:14 am
EYW
-
BOS
9h 19m
1 stop
United Airlines Logo
7:19 am - 3:07 pm
BOS
-
EYW
7h 48m
1 stop
$265United Airlines
Thu, May 21 - Tue, May 26
United Airlines Logo
3:55 pm - 1:14 am
EYW
-
BOS
9h 19m
1 stop
United Airlines Logo
5:45 am - 3:07 pm
BOS
-
EYW
9h 22m
2 stops
$270United Airlines
Thu, May 21 - Tue, May 26
American Airlines Logo
7:29 pm - 12:40 am
EYW
-
BOS
5h 11m
1 stop
American Airlines Logo
8:00 am - 4:07 pm
BOS
-
EYW
8h 07m
1 stop
$278American Airlines
Thu, May 21 - Tue, May 26
American Airlines Logo
7:40 pm - 12:59 am
EYW
-
BOS
5h 19m
1 stop
American Airlines Logo
8:00 am - 4:07 pm
BOS
-
EYW
8h 07m
2 stops
$283American Airlines
Tue, May 12 - Sat, May 16
Multiple Airlines Logo
1:14 pm - 1:24 am
EYW
-
BOS
36h 10m
2 stops
Multiple Airlines Logo
7:00 am - 11:25 am
BOS
-
EYW
28h 25m
1 stop
$286Multiple Airlines
Fri, May 22 - Mon, May 25
Multiple Airlines Logo
10:31 am - 8:55 am
EYW
-
BOS
22h 24m
1 stop
Multiple Airlines Logo
12:01 pm - 11:06 am
BOS
-
EYW
47h 05m
2 stops
$301Multiple Airlines
Mon, May 25 - Sun, May 31
Breeze Airways Logo
12:07 pm - 5:27 pm
EYW
-
BDL
29h 20m
2 stops
Breeze Airways Logo
6:20 am - 10:27 am
BDL
-
EYW
28h 07m
1 stop
$359Breeze Airways
Mon, May 25 - Sun, May 31
Breeze Airways Logo
12:07 pm - 5:27 pm
EYW
-
BDL
29h 20m
2 stops
Breeze Airways Logo
6:20 am - 10:27 am
BDL
-
EYW
28h 07m
1 stop
$365Breeze Airways
Booking Insights

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

Get data-powered insights and trends into flights from Key West to Massachusetts 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 Massachusetts?

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 Massachusetts departing in May.

What is the cheapest Key West to Massachusetts flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Massachusetts from Key West found in the last 72 hours was to Boston, at $497 round-trip. The most popular route is from Key West (EYW) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $497.

What is the cheapest time of day to fly to Massachusetts?

The average price for all round-trip flights from Key West to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally in the evening, when round-trip flights cost $332 on average. Morning departures are around 44% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $479.

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

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 2 stops layover the cheapest option at $348 on average.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Key West to Massachusetts, 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 Massachusetts is November, when tickets cost $170 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $478 and $316 respectively.

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

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

If your flying dates are flexible, you should consider flying to Massachusetts 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 Massachusetts. For your return ticket, we recommend flying on a Monday and avoiding Thursdays for the best deals.

Good to know

Low seasonMarch
Cheapest flight$93
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 Hartford

FAQs - booking Massachusetts flights

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

    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 Massachusetts.

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

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

    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 from Key West to Massachusetts with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Massachusetts?

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

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Key West to the following destinations at these prices or less: Boston $312 one-way - $627 round-trip

Reviews of the top airlines flying from Key West to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Key West to Massachusetts. 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 Massachusetts? 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.
7.1
JetBlueOverall score based on 2969 reviews
7.5Comfort
7.3Boarding
7.2Entertainment
7.9Crew
6.6Food
Airline reviews

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

8.0 ExcellentChristopher, Apr 2026
LAS - BOS
Read more JetBlue reviews

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

Not having an assigned seat until boarding and then having to check my bag.

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!

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?

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 Massachusetts

Information on your arrival and departure airports