$109 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 5/11. 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$241
Albany
Albany2 stops$307
Boston
Boston1 stop$241
Albany
Albany2 stops$307

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, Feb 25 - Thu, Feb 26
Multiple Airlines Logo
11:50 am - 10:50 am
ISP
-
BOS
23h 00m
1 stop
Multiple Airlines Logo
4:22 pm - 7:38 am
BOS
-
ISP
15h 16m
1 stop
$241Multiple Airlines
Fri, Feb 27 - Tue, Mar 3
Multiple Airlines Logo
2:31 pm - 10:50 am
ISP
-
BOS
20h 19m
1 stop
Multiple Airlines Logo
4:22 pm - 8:40 am
BOS
-
ISP
16h 18m
1 stop
$260Multiple Airlines
Fri, Feb 27 - Tue, Mar 3
Multiple Airlines Logo
2:31 pm - 10:50 am
ISP
-
BOS
20h 19m
1 stop
Multiple Airlines Logo
12:43 pm - 11:10 am
BOS
-
ISP
22h 27m
2 stops
$275Multiple Airlines
Wed, Feb 25 - Thu, Feb 26
Multiple Airlines Logo
11:50 am - 10:50 am
ISP
-
BOS
23h 00m
1 stop
Multiple Airlines Logo
6:10 pm - 2:39 pm
BOS
-
ISP
20h 29m
2 stops
$280Multiple Airlines
Fri, Feb 27 - Sun, Mar 1
Multiple Airlines Logo
2:31 pm - 10:50 am
ISP
-
BOS
20h 19m
1 stop
Multiple Airlines Logo
12:30 pm - 7:38 am
BOS
-
ISP
19h 08m
1 stop
$293Multiple Airlines
Sun, May 17 - Thu, May 21
Multiple Airlines Logo
4:07 pm - 10:21 am
ISP
-
BOS
18h 14m
1 stop
Multiple Airlines Logo
7:00 am - 9:08 am
BOS
-
ISP
26h 08m
1 stop
$305Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Breeze Airways Logo
7:26 pm - 9:20 am
ISP
-
ALB
13h 54m
2 stops
Breeze Airways Logo
12:01 pm - 1:31 pm
ALB
-
ISP
25h 30m
1 stop
$325Breeze Airways
Thu, May 14 - Sat, May 16
Southwest Logo
4:30 pm - 9:50 pm
ISP
-
BOS
5h 20m
1 stop
Southwest Logo
7:25 pm - 11:20 pm
BOS
-
ISP
3h 55m
1 stop
$327Southwest
Sun, Mar 1 - Tue, Mar 31
Southwest Logo
5:35 pm - 9:05 pm
ISP
-
ALB
3h 30m
1 stop
Southwest Logo
4:45 pm - 10:50 pm
ALB
-
ISP
6h 05m
1 stop
$378Southwest
Thu, May 21 - Mon, May 25
Cape Air Logo
12:30 pm - 3:35 pm
ISP
-
MVY
3h 05m
1 stop
Cape Air Logo
4:30 pm - 7:45 pm
MVY
-
ISP
3h 15m
1 stop
$1,249Cape 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 $580 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 $580.

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$109
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly and prices are also 58% 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 $498 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
9.1Boarding
8.7Comfort
9.5Crew
8.8Food
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 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°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

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