$127 Find Cheap Flights from Islip 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 Islip to Massachusetts departing on 4/14. 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 Islip 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 Islip to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Islip to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$327
Albany
Albany1 stop$314
Boston
Boston1 stop$327
Albany
Albany1 stop$314

Book Cheap Islip 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 Islip 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 Islip to Massachusetts

Mon, Mar 16 - Fri, Mar 20
Breeze Airways Logo
2:31 pm - 11:33 am
ISP
-
ALB
21h 02m
1 stop
Breeze Airways Logo
7:09 pm - 11:10 am
ALB
-
ISP
16h 01m
1 stop
$314Breeze Airways
Thu, Apr 30 - Mon, May 4
Southwest Logo
8:35 am - 12:10 pm
ISP
-
BOS
3h 35m
1 stop
Southwest Logo
5:30 am - 11:50 am
BOS
-
ISP
6h 20m
1 stop
$327Southwest
Sun, Mar 29 - Thu, Apr 2
Multiple Airlines Logo
7:26 pm - 11:41 am
ISP
-
BOS
40h 15m
2 stops
Multiple Airlines Logo
9:45 am - 7:51 pm
BOS
-
ISP
10h 06m
1 stop
$334Multiple Airlines
Tue, Mar 31 - Wed, Apr 1
Southwest Logo
5:45 am - 10:50 am
ISP
-
BOS
5h 05m
1 stop
Southwest Logo
5:45 am - 11:40 am
BOS
-
ISP
5h 55m
1 stop
$337Southwest
Sat, Jul 11 - Sun, Jul 19
Southwest Logo
12:15 pm - 3:45 pm
ISP
-
BOS
3h 30m
1 stop
Southwest Logo
9:40 pm - 8:20 am
BOS
-
ISP
10h 40m
1 stop
$342Southwest
Mon, Mar 23 - Fri, Mar 27
Multiple Airlines Logo
1:22 pm - 11:41 am
ISP
-
BOS
22h 19m
2 stops
Multiple Airlines Logo
12:56 pm - 11:10 am
BOS
-
ISP
22h 14m
1 stop
$356Multiple Airlines
Wed, Jun 10 - Wed, Jun 17
JetBlue Logo
12:25 pm - 11:27 pm
ISP
-
BOS
11h 02m
1 stop
JetBlue Logo
1:28 pm - 11:17 pm
BOS
-
ISP
9h 49m
1 stop
$373JetBlue
Fri, Mar 27 - Mon, Mar 30
JetBlue Logo
8:25 am - 3:50 pm
ISP
-
ORH
7h 25m
1 stop
JetBlue Logo
4:55 pm - 12:08 am
ORH
-
ISP
7h 13m
1 stop
$673JetBlue
Fri, May 22 - Mon, May 25
Cape Air Logo
7:25 am - 6:49 am
ISP
-
MVY
23h 24m
2 stops
Cape Air Logo
7:10 pm - 4:10 pm
MVY
-
ISP
21h 00m
2 stops
$982Cape Air
Fri, Aug 28 - Mon, Aug 31
Cape Air Logo
7:25 am - 6:18 am
ISP
-
MVY
22h 53m
2 stops
Cape Air Logo
2:22 pm - 4:10 pm
MVY
-
ISP
25h 48m
2 stops
$1,002Cape Air
Booking Insights

KAYAK's insights & trends for Islip to Massachusetts flights

Get data-powered insights and trends into flights from Islip to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Islip to Massachusetts flight route?

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

The cheapest ticket to Massachusetts from Islip found in the last 72 hours was to Boston, at $520 round-trip. The most popular route is from Islip (ISP) to Boston (BOS), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $520.

Can I save money by flying with a layover from Islip 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 $580, prices are generally cheapest when you fly direct.

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

The average price of all round-trip flights from Islip 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 Islip to Massachusetts. For your return ticket, we recommend flying on a Thursday and avoiding Sundays for the best deals.

Good to know

Low seasonMay
Cheapest flight$127
Best time to beat the crowds with an average 57% drop in price.
Most popular time to fly and prices are also 57% lower on average.
Flight from Islip to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Islip 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 Islip to Massachusetts.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Islip 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 Islip 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 Islip 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 Islip 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 Islip 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 $504 on average. 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 $520.

Reviews of the top 3 airlines serving from Islip to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Islip 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 Islip 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.
9.3
Cape AirOverall score based on 36 reviews
8.7Comfort
8.8Food
9.5Crew
9.1Boarding
9.0Entertainment
Airline reviews

We were the only ones on the plane to Culebra, and left 24 minutes early. Flight was beautiful to boot!

10.0 ExcellentAnonymous, Oct 2025
CPX - SJU
Read more Cape Air reviews

We were the only ones on the plane to Culebra, and left 24 minutes early. Flight was beautiful to boot!

Cape Air was great. Kayak was very poor. No ticket to print or explanation that they transferred to another service.

It was good. It was convenient and frequent enough to be a very useful flight to reach more regional hubs. I felt comfortable enough to sleep. During the flight but loved seeing the countryside when I was awake.

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

Everything you need to know for your flight from Islip to Massachusetts

Information on your arrival and departure airports