$89 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 2/15. 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, Feb 6 - Mon, Feb 9
Spirit Airlines Logo
2:25 pm - 11:57 pm
EYW
-
BOS
9h 32m
1 stop
Spirit Airlines Logo
5:34 am - 1:30 pm
BOS
-
EYW
7h 56m
1 stop
$200Spirit Airlines
Fri, Feb 13 - Fri, Feb 20
Spirit Airlines Logo
2:25 pm - 11:44 pm
EYW
-
BOS
9h 19m
1 stop
Spirit Airlines Logo
5:27 am - 1:30 pm
BOS
-
EYW
8h 03m
1 stop
$209Spirit Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
2:25 pm - 11:49 pm
EYW
-
BOS
9h 24m
2 stops
United Airlines Logo
6:00 am - 3:17 pm
BOS
-
EYW
9h 17m
1 stop
$222United Airlines
Fri, Feb 27 - Mon, Mar 2
JetBlue Logo
12:48 pm - 4:24 pm
EYW
-
BOS
3h 36mnonstop
JetBlue Logo
8:00 am - 11:58 am
BOS
-
EYW
3h 58mnonstop
$227JetBlue
Tue, May 26 - Mon, Jun 1
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
$232Breeze Airways
Thu, May 28 - Mon, Jun 1
Breeze Airways Logo
12:05 pm - 11:11 pm
EYW
-
BDL
11h 06m
2 stops
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
$237Breeze Airways
Tue, May 26 - Fri, May 29
Breeze Airways Logo
1:14 pm - 4:30 pm
EYW
-
BDL
27h 16m
1 stop
Breeze Airways Logo
7:25 am - 12:31 pm
BDL
-
EYW
5h 06m
1 stop
$240Breeze Airways
Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
2:25 pm - 9:52 pm
EYW
-
BOS
7h 27m
1 stop
United Airlines Logo
9:30 am - 4:22 pm
BOS
-
EYW
6h 52m
1 stop
$247United Airlines
Fri, Mar 13 - Mon, Mar 16
Multiple Airlines Logo
2:35 pm - 11:59 pm
EYW
-
BOS
9h 24m
1 stop
Multiple Airlines Logo
8:04 am - 11:59 am
BOS
-
EYW
3h 55mnonstop
$253Multiple Airlines
Tue, Feb 24 - Sat, Feb 28
Multiple Airlines Logo
1:01 pm - 5:23 pm
EYW
-
BDL
28h 22m
2 stops
Multiple Airlines Logo
9:05 pm - 9:06 am
BDL
-
EYW
12h 01m
1 stop
$255Multiple 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 $195 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 $195.

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 $381, 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, Monday 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$64
Best time to beat the crowds but there is an average 57% increase in price.
Most popular time to fly and prices are also 11% 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 morning, when round-trip flights cost $331 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Massachusetts is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $440.

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 $213 one-way - $242 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 11197 reviews
7.5Boarding
7.2Comfort
6.9Entertainment
8.0Crew
6.4Food
Airline reviews

No enough space plus only allowing one laggage instead of two like other airlines.

8.0 ExcellentAnonymous, Jan 2026
STL - BOS
Read more American Airlines reviews

No enough space plus only allowing one laggage instead of two like other airlines.

Qatar airways ,boarding arrangements at Hamid international airport could been better

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

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.

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

Information on your arrival and departure airports