$86 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 9/30. 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

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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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Cheap Flights from Key West to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$171
Boston
Boston1 stop$171

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

Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
6:17 pm - 11:44 pmEYW-BOS
5h 27m1 stop
American Airlines Logo
6:00 am - 12:58 pmBOS-EYW
6h 58m1 stop
$171American Airlines
Find Deal
Tue, Sep 23 - Tue, Oct 7
American Airlines Logo
11:25 am - 7:42 pmEYW-BOS
8h 17m2 stops
American Airlines Logo
7:00 am - 12:55 pmBOS-EYW
5h 55m1 stop
$176American Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
Delta Logo
2:00 pm - 8:27 pmEYW-BDL
6h 27m1 stop
Delta Logo
1:22 pm - 8:07 pmBDL-EYW
6h 45m1 stop
$283Delta
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Tue, Sep 23 - Tue, Sep 30
Delta Logo
6:00 pm - 11:52 pmEYW-BDL
5h 52m1 stop
Delta Logo
6:00 am - 1:02 pmBDL-EYW
7h 02m1 stop
$306Delta
Find Deal
Wed, Aug 13 - Sun, Aug 17
United Airlines Logo
2:12 pm - 11:59 pmEYW-BOS
9h 47m2 stops
United Airlines Logo
6:05 am - 12:41 pmBOS-EYW
6h 36m1 stop
$322United Airlines
Find Deal
Fri, Sep 26 - Thu, Oct 2
Breeze Airways Logo
8:47 am - 5:56 pmEYW-BDL
9h 09m2 stops
Breeze Airways Logo
12:55 pm - 10:31 amBDL-EYW
21h 36m1 stop
$379Breeze Airways
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Fri, Aug 15 - Sun, Aug 17
 Logo
10:23 am - 9:38 pmEYW-BDL
11h 15m1 stop
 Logo
6:15 pm - 4:41 pmBDL-EYW
22h 26m2 stops
Fri, Sep 12 - Sun, Sep 14
 Logo
12:09 pm - 11:13 amEYW-BOS
23h 04m2 stops
 Logo
2:18 pm - 11:52 amBOS-EYW
21h 34m3 stops
Thu, Sep 25 - Tue, Sep 30
United Airlines Logo
3:12 pm - 9:37 amEYW-BDL
18h 25m2 stops
United Airlines Logo
6:00 am - 2:29 pmBDL-EYW
8h 29m2 stops
$458United Airlines
Find Deal
Thu, Sep 25 - Sun, Sep 28
Breeze Airways Logo
10:59 am - 12:45 pmEYW-BDL
25h 46m1 stop
Breeze Airways Logo
12:55 pm - 11:52 amBDL-EYW
22h 57m2 stops
$523Breeze Airways
Find Deal
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?

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 $316 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
Cheapest flight$86
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.

Reviews of the 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 7980 reviews
8.5Crew
8.2Boarding
7.9Entertainment
7.9Comfort
7.3Food
Airline reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

2.0 MediocreRosa, Jul 2025TPA - JFK
Read more Delta reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

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.

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.

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 very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

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.

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

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