$129 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 10/8. 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

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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Best Massachusetts Flight Deals from Key West

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$257
Boston
Boston1 stop$257

Cheap Flights from Key West to Massachusetts

 
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

Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
7:31 pm - 12:44 amEYW-BOS
5h 13m1 stop
American Airlines Logo
9:19 am - 4:29 pmBOS-EYW
7h 10m1 stop
$257American Airlines
Find Deal
Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
11:25 am - 8:57 pmEYW-BOS
9h 32m2 stops
American Airlines Logo
5:55 am - 11:30 amBOS-EYW
5h 35m1 stop
$262American Airlines
Find Deal
Fri, Aug 29 - Wed, Sep 3
Delta Logo
6:20 pm - 1:20 amEYW-BOS
7h 00m1 stop
Delta Logo
5:35 am - 1:05 pmBOS-EYW
7h 30m1 stop
$287Delta
Find Deal
Fri, Aug 29 - Wed, Sep 3
American Airlines Logo
7:40 pm - 12:48 amEYW-BOS
5h 08m1 stop
American Airlines Logo
5:50 am - 1:27 pmBOS-EYW
7h 37m2 stops
$292American Airlines
Find Deal
Sat, Aug 30 - Fri, Sep 5
American Airlines Logo
1:58 pm - 11:43 pmEYW-BOS
9h 45m2 stops
American Airlines Logo
10:29 am - 5:46 pmBOS-EYW
7h 17m2 stops
$297American Airlines
Find Deal
Fri, Aug 15 - Wed, Aug 20
Delta Logo
2:00 pm - 10:21 pmEYW-BDL
8h 21m1 stop
Delta Logo
2:31 pm - 8:12 pmBDL-EYW
5h 41m1 stop
$338Delta
Find Deal
Tue, Jul 1 - Mon, Jul 7
United Airlines Logo
2:12 pm - 11:59 pmEYW-BOS
9h 47m2 stops
United Airlines Logo
7:00 am - 1:12 pmBOS-EYW
6h 12m1 stop
$372United Airlines
Find Deal
Sun, Jun 29 - Thu, Jul 3
 Logo
4:17 pm - 8:12 amEYW-BOS
15h 55m1 stop
 Logo
3:26 pm - 4:36 pmBOS-EYW
25h 10m2 stops
Sat, Jun 28 - Sun, Jun 29
United Airlines Logo
2:12 pm - 9:24 pmEYW-BOS
7h 12m1 stop
United Airlines Logo
6:05 am - 12:41 pmBOS-EYW
6h 36m1 stop
$478United Airlines
Find Deal
Sun, Jun 29 - Thu, Jul 3
 Logo
4:17 pm - 3:37 pmEYW-BOS
23h 20m2 stops
 Logo
3:26 pm - 4:36 pmBOS-EYW
25h 10m2 stops
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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?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Key West to Massachusetts.

The cheapest ticket to Massachusetts from Key West found in the last 72 hours was to Boston, at $156 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 $156.

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 1 stop layover the cheapest option at $329 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 September, when tickets cost $300 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $577 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 Saturday, 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 Saturday and avoiding Thursdays for the best deals.


Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$129
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 46% increase in price.
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 $338 on average. Morning departures are around 50% 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 $508.

Top 3 airlines serving 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.
8.0
DeltaOverall score based on 7963 reviews
7.9Comfort
7.3Food
8.5Crew
7.9Entertainment
8.2Boarding
Airline reviews

Excellent check-in. Crew was good. Excellent communication from flight deck.

8.0 ExcellentPatrick, Jun 2025JAX - BOS
Read more Delta reviews

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

Simply outstanding. Their new lounge for Delta One customers is a cut above the rest.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

They have lost any customer service care and support. Terrible airline now and been for awhile.

The flight was delayed leaving Miami. When we arrived in Charlotte, we were unable to park at our scheduled gate. We had to wait another 30-45 minutes before we could park at a different gate. All in all, we were delayed by almost two hours arriving in Charlotte.

the pilot that landed this flight in Philadelphia did an amazing job, the weather was absolutely terrible and we landed safely.

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

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