$153 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 3/10. 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
Boston2 stops$290
Albany
Albany1 stop$308
Boston
Boston2 stops$290
Albany
Albany1 stop$308

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 30 - Sat, Apr 4
Multiple Airlines Logo
2:31 pm - 1:13 am
ISP
-
BOS
34h 42m
2 stops
Multiple Airlines Logo
7:14 pm - 11:13 am
BOS
-
ISP
15h 59m
1 stop
$290Multiple Airlines
Thu, Apr 30 - Fri, May 1
Southwest Logo
4:30 pm - 11:15 pm
ISP
-
ALB
6h 45m
1 stop
Southwest Logo
2:55 pm - 8:25 pm
ALB
-
ISP
5h 30m
1 stop
$308Southwest
Tue, Mar 24 - Thu, Mar 26
Multiple Airlines Logo
11:59 am - 10:29 pm
ISP
-
BOS
10h 30m
1 stop
Multiple Airlines Logo
12:56 pm - 1:31 pm
BOS
-
ISP
24h 35m
1 stop
$319Multiple Airlines
Sun, Mar 29 - Sun, Apr 5
Multiple Airlines Logo
7:26 pm - 11:41 am
ISP
-
BOS
40h 15m
2 stops
Multiple Airlines Logo
4:23 pm - 9:28 am
BOS
-
ISP
17h 05m
1 stop
$324Multiple Airlines
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
10:55 am - 5:30 pm
ISP
-
ALB
6h 35m
1 stop
Southwest Logo
11:25 am - 2:30 pm
ALB
-
ISP
3h 05m
1 stop
$327Southwest
Wed, Aug 19 - Sat, Aug 22
Southwest Logo
6:05 am - 3:35 pm
ISP
-
ALB
9h 30m
2 stops
Southwest Logo
11:25 am - 2:30 pm
ALB
-
ISP
3h 05m
1 stop
$332Southwest
Mon, Mar 30 - Sat, Apr 4
Southwest Logo
6:00 am - 9:50 am
ISP
-
BOS
3h 50m
1 stop
Southwest Logo
5:15 am - 11:40 am
BOS
-
ISP
6h 25m
1 stop
$347Southwest
Fri, Mar 20 - Sun, Mar 22
Breeze Airways Logo
7:20 pm - 10:15 am
ISP
-
ALB
14h 55m
1 stop
Breeze Airways Logo
12:01 pm - 1:31 pm
ALB
-
ISP
25h 30m
1 stop
$965Breeze Airways
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
$1,172Cape Air
Fri, Aug 28 - Mon, Aug 31
Cape Air Logo
9:59 am - 1:54 pm
ISP
-
MVY
3h 55m
1 stop
Cape Air Logo
2:22 pm - 4:10 pm
MVY
-
ISP
25h 48m
2 stops
$1,194Cape 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.

How much is a round-trip flight from Islip, New York to Massachusetts?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Islip, New York to Massachusetts departing in March.

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$187
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
8.8Food
8.7Comfort
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.

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.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

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.

very difficult boarding process - aggressive passengers not the friendliest crew

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

Information on your arrival and departure airports