$168 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 8/25. 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$347
Albany
Albany1 stop$362
Boston
Boston1 stop$347
Albany
Albany1 stop$362

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

Fri, Jul 10 - Mon, Jul 13
Southwest Logo
6:00 pm - 12:10 am
ISP
-
BOS
6h 10m
1 stop
Southwest Logo
7:50 pm - 11:40 pm
BOS
-
ISP
3h 50m
1 stop
$347Southwest
Mon, Aug 24 - Mon, Aug 31
Southwest Logo
12:35 pm - 9:50 pm
ISP
-
BOS
9h 15m
2 stops
Southwest Logo
5:30 pm - 10:05 pm
BOS
-
ISP
4h 35m
1 stop
$352Southwest
Wed, Jul 8 - Fri, Jul 10
Southwest Logo
6:00 am - 9:50 am
ISP
-
BOS
3h 50m
1 stop
Southwest Logo
7:50 pm - 11:40 pm
BOS
-
ISP
3h 50m
1 stop
$357Southwest
Fri, Jun 26 - Fri, Jul 3
Southwest Logo
3:05 pm - 11:45 pm
ISP
-
ALB
8h 40m
1 stop
Southwest Logo
5:55 pm - 11:35 pm
ALB
-
ISP
5h 40m
1 stop
$362Southwest
Fri, Jun 26 - Sun, Jun 28
Southwest Logo
3:05 pm - 12:05 am
ISP
-
BOS
9h 00m
1 stop
Southwest Logo
5:30 am - 11:45 am
BOS
-
ISP
6h 15m
1 stop
$362Southwest
Thu, Jun 11 - Mon, Jun 15
Breeze Airways Logo
7:49 pm - 9:17 am
ISP
-
ALB
13h 28m
2 stops
Breeze Airways Logo
8:17 pm - 6:38 pm
ALB
-
ISP
22h 21m
1 stop
$427Breeze Airways
Fri, Jun 26 - Fri, Jul 3
Breeze Airways Logo
8:43 pm - 5:26 pm
ISP
-
ALB
20h 43m
2 stops
Breeze Airways Logo
9:57 am - 1:33 pm
ALB
-
ISP
27h 36m
1 stop
$428Breeze Airways
Sat, Aug 29 - Wed, Sep 2
Cape Air Logo
3:05 pm - 6:30 am
ISP
-
MVY
39h 25m
2 stops
Cape Air Logo
10:30 pm - 8:15 pm
MVY
-
ISP
21h 45m
2 stops
$942Cape Air
Wed, Jul 15 - Sat, Jul 18
Multiple Airlines Logo
7:26 am - 12:36 pm
ISP
-
MVY
5h 10m
1 stop
Multiple Airlines Logo
10:58 am - 6:35 pm
MVY
-
ISP
7h 37m
1 stop
$955Multiple Airlines
Sat, Aug 29 - Wed, Sep 2
Cape Air Logo
3:05 pm - 2:04 pm
ISP
-
MVY
22h 59m
1 stop
Cape Air Logo
10:30 pm - 8:15 pm
MVY
-
ISP
21h 45m
2 stops
$1,024Cape 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 July.

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 3 days was to Boston, at $508 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 3 days was $508.

What is the cheapest time of day to fly to Massachusetts?

The average price for all round-trip flights from Islip to Massachusetts depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $520 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 $531.

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 $561, 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 February, when tickets cost $0 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $511 and $507 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 Monday, 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 Wednesday and avoiding Sundays for the best deals.

Good to know

Low seasonJuly
Cheapest flight$168
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Islip to Albany

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.

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 $249 one-way - $530 round-trip

Reviews of the top airlines flying 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 33 reviews
8.9Entertainment
9.0Boarding
8.7Food
8.6Comfort
9.4Crew
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 first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

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

Information on your arrival and departure airports