$79 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 12/18. 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

Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
1:06 pm - 11:19 pm
EYW
-
BOS
10h 13m1 stop
Multiple Airlines Logo
7:00 am - 12:26 pm
BOS
-
EYW
29h 26m1 stop
$188Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
1:06 pm - 11:19 pm
EYW
-
BOS
10h 13m1 stop
Multiple Airlines Logo
5:27 pm - 12:26 pm
BOS
-
EYW
18h 59m2 stops
$197Multiple Airlines
Wed, Mar 4 - Tue, Mar 10
Delta Logo
6:07 pm - 1:09 am
EYW
-
BOS
7h 02m1 stop
Delta Logo
11:10 am - 7:41 pm
BOS
-
EYW
8h 31m1 stop
$217Delta
Fri, May 1 - Tue, May 5
United Airlines Logo
2:30 pm - 8:13 pm
EYW
-
BOS
5h 43m1 stop
United Airlines Logo
6:00 am - 2:59 pm
BOS
-
EYW
8h 59m1 stop
$227United Airlines
Fri, May 1 - Tue, May 5
United Airlines Logo
2:30 pm - 8:13 pm
EYW
-
BOS
5h 43m1 stop
United Airlines Logo
6:00 am - 2:59 pm
BOS
-
EYW
8h 59m2 stops
$232United Airlines
Fri, May 8 - Wed, May 13
Delta Logo
6:00 pm - 1:03 am
EYW
-
BOS
7h 03m1 stop
Delta Logo
12:45 pm - 7:44 pm
BOS
-
EYW
6h 59m1 stop
$247Delta
Fri, Jan 9 - Fri, Jan 16
Multiple Airlines Logo
1:06 pm - 11:19 pm
EYW
-
BOS
10h 13m1 stop
Multiple Airlines Logo
7:00 am - 11:56 am
BOS
-
EYW
52h 56m2 stops
$248Multiple Airlines
Fri, Jan 23 - Sun, Jan 25
JetBlue Logo
1:00 pm - 4:36 pm
EYW
-
BOS
3h 36mnonstop
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
$273JetBlue
Thu, May 7 - Sun, May 10
Delta Logo
6:00 pm - 1:03 am
EYW
-
BOS
7h 03m1 stop
Delta Logo
10:30 am - 5:12 pm
BOS
-
EYW
6h 42m1 stop
$288Delta
Fri, Jan 9 - Sun, Jan 11
United Airlines Logo
6:05 pm - 11:44 pm
EYW
-
BDL
5h 39m1 stop
United Airlines Logo
6:00 am - 3:17 pm
BDL
-
EYW
9h 17m2 stops
$294United Airlines
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.

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 $307 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 $307.

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.

No, with an average price for the route of $353, prices are generally cheapest when you fly direct.

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 $301 (return) on average. On the other hand, the most expensive months are September and April, when the average cost of round-trip tickets is $609 and $545 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 Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Key West to Massachusetts. For your return ticket, we recommend flying on a Sunday and avoiding Thursdays for the best deals.

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds but there is an average 54% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Key West to Boston

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.

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

    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 42% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally at night, which is peak travel time and where the average cost of a ticket is $475.

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 $201 one-way - $440 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.
7.2
American AirlinesOverall score based on 11048 reviews
8.0Crew
7.2Comfort
7.5Boarding
6.9Entertainment
6.5Food
Airline reviews

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

8.0 ExcellentJolene, Dec 2025
GNV - DFW
Read more American Airlines reviews

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

The captain gave good announcements and the flight attendants were friendly. The WiFi was pretty good. The plane itself looked very old inside and the seats were very uncomfortable. The screens in the seat backs were the smallest I’ve ever seen. There were so many loud and obnoxious kids on this flight and the parents didn’t do much to try to quiet them down. Some had videos and games on tablets with higher than necessary volume going the whole time.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

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

Information on your arrival and departure airports