$92 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 1/22. 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$216
Albany
Albany1 stop$309
Boston
Boston1 stop$216
Albany
Albany1 stop$309

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

Wed, Jan 14 - Mon, Jan 19
Southwest Logo
3:45 pm - 10:05 pmISP-BOS
6h 20m1 stop
Southwest Logo
5:50 am - 11:55 amBOS-ISP
6h 05m1 stop
$216Southwest
Find Deal
Wed, Dec 17 - Sun, Dec 21
Multiple Airlines Logo
6:00 am - 9:52 amISP-BOS
27h 52m1 stop
Multiple Airlines Logo
10:56 am - 7:40 pmBOS-ISP
8h 44m1 stop
$265Multiple Airlines
Find Deal
Tue, Dec 9 - Tue, Dec 16
Multiple Airlines Logo
8:29 pm - 10:01 amISP-BOS
13h 32m1 stop
Multiple Airlines Logo
8:11 pm - 10:44 pmBOS-ISP
26h 33m1 stop
$267Multiple Airlines
Find Deal
Tue, Dec 9 - Wed, Dec 10
Multiple Airlines Logo
8:29 pm - 10:01 amISP-BOS
13h 32m1 stop
Multiple Airlines Logo
8:11 pm - 9:13 amBOS-ISP
13h 02m1 stop
$269Multiple Airlines
Find Deal
Mon, Jan 5 - Tue, Jan 6
Southwest Logo
10:55 am - 5:15 pmISP-BOS
6h 20m1 stop
Southwest Logo
9:35 am - 4:15 pmBOS-ISP
6h 40m1 stop
$276Southwest
Find Deal
Mon, Jan 5 - Tue, Jan 6
Southwest Logo
5:50 am - 9:45 amISP-BOS
3h 55m1 stop
Southwest Logo
5:30 am - 4:15 pmBOS-ISP
10h 45m2 stops
$281Southwest
Find Deal
Mon, Feb 2 - Thu, Feb 5
Breeze Airways Logo
2:01 pm - 12:25 pmISP-ALB
22h 24m1 stop
Breeze Airways Logo
12:01 pm - 1:31 pmALB-ISP
25h 30m1 stop
$467Breeze Airways
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Mon, Feb 2 - Thu, Feb 5
Breeze Airways Logo
7:20 pm - 12:25 pmISP-ALB
17h 05m2 stops
Breeze Airways Logo
12:01 pm - 1:31 pmALB-ISP
25h 30m1 stop
$596Breeze Airways
Find Deal
Thu, Dec 18 - Mon, Dec 22
Cape Air Logo
9:59 am - 3:35 pmISP-MVY
5h 36m1 stop
Cape Air Logo
7:10 pm - 4:10 pmMVY-ISP
21h 00m2 stops
$856Cape Air
Find Deal
Thu, Dec 18 - Mon, Dec 22
Cape Air Logo
9:59 am - 6:49 amISP-MVY
20h 50m2 stops
Cape Air Logo
7:10 pm - 11:05 amMVY-ISP
15h 55m2 stops
$877Cape Air
Find Deal
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 $503 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 $503.

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 $565, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Islip to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Islip 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 Islip to Massachusetts is May, when tickets cost $157 (return) on average. On the other hand, the most expensive months are November and January, when the average cost of round-trip tickets is $620 and $520 respectively.

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, Tuesday 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 seasonFebruary
Cheapest flight$92
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 62% 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 $240 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.

Top tips for finding cheap flights to Massachusetts

  • Looking for a cheap flight? 25% of our users found tickets from Islip to the following destinations at these prices or less: Boston $320 one-way - $520 round-trip

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.
9.4
Cape AirOverall score based on 37 reviews
9.5Crew
9.0Entertainment
8.9Food
8.8Comfort
9.1Boarding
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 2025CPX - 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.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

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.

very difficult boarding process - aggressive passengers not the friendliest crew

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

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.

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.

Communication since no reason or explanation was given for 3 hrs delay

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.

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

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