ISP - BOS

$129 Find Cheap Flights from Islip to Boston

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 Boston departing on 5/17. 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 Boston

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Islip to Boston, 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 Boston, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$327
Southwest
Thu 4/30Mon 5/4
ISP - BOS • 1 stop
Cheapest non-stop
$498
Typical prices: $507-$520
Cape Air
Fri 3/27Mon 3/30
ISP - BOS • Non-stop
Top airlines
Southwest
Cheapest • from $327 (round-trip)
Cape Air
Best reviews • 9.3 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with Cape Air. Average duration is 1h 25m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Boston!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Islip to Boston (ISP-BOS)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Islip to Boston 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 Boston

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
Tue, Aug 11 - Sat, Aug 15
Southwest Logo
6:05 am - 4:10 pm
ISP
-
BOS
10h 05m
2 stops
Southwest Logo
8:10 am - 2:30 pm
BOS
-
ISP
6h 20m
1 stop
$332Southwest
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
Fri, Aug 7 - Mon, Aug 10
Southwest Logo
10:20 am - 2:30 pm
ISP
-
BOS
4h 10m
1 stop
Southwest Logo
9:40 am - 4:25 pm
BOS
-
ISP
6h 45m
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
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
12:25 pm - 5:45 pm
ISP
-
BOS
5h 20m
1 stop
Southwest Logo
11:35 am - 4:00 pm
BOS
-
ISP
4h 25m
1 stop
$347Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
9:00 am - 3:40 pm
ISP
-
BOS
6h 40m
1 stop
Southwest Logo
5:35 am - 1:45 pm
BOS
-
ISP
8h 10m
2 stops
$352Southwest
Fri, Jul 31 - Sun, Aug 2
Southwest Logo
12:30 pm - 5:10 pm
ISP
-
BOS
4h 40m
1 stop
Southwest Logo
5:30 am - 11:45 am
BOS
-
ISP
6h 15m
1 stop
$357Southwest
Sat, Mar 28 - Wed, Apr 1
Southwest Logo
5:50 pm - 12:05 am
ISP
-
BOS
6h 15m
1 stop
Southwest Logo
5:45 am - 11:40 am
BOS
-
ISP
5h 55m
1 stop
$367Southwest
Sat, Mar 28 - Wed, Apr 1
Southwest Logo
5:50 pm - 12:05 am
ISP
-
BOS
6h 15m
1 stop
Southwest Logo
2:00 pm - 10:50 pm
BOS
-
ISP
8h 50m
2 stops
$372Southwest
Booking Insights

KAYAK's insights & trends for Islip to Boston flights

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

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

The average price of all round-trip flights from Islip to Boston clicked on KAYAK for each day over the last 12 months.

When flying from Islip to Boston, you should consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Islip, you’ll find the best rates on Thursdays and the most expensive ones on Sundays.

Can I save money by flying with a layover from Islip to Boston?

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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $511 on average.

Good to know

Low seasonMay
Cheapest flight$129
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

When to book flights from Islip to Boston

Are your dates flexible? Find out the best times to travel from Islip to Boston based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Islip to Boston

  • What is the cheapest flight from Islip to Boston?

    In the last 3 days, the lowest price for a flight from Islip to Boston was $129 for a one-way ticket and $327 for a round-trip.

  • Do I need a passport to fly between Islip and Boston?

    No, a passport isn't needed to fly from Islip to Boston. However, local authorities might ask for an official ID.

  • Which airlines offer Wi-Fi service onboard planes from Islip to Boston?

    Delta, JetBlue, Alaska Airlines, and American Airlines offer inflight Wi-Fi service on the Islip to Boston flight route.

  • Which aircraft models fly most regularly from Islip to Boston?

    The Cessna light aircraft is the aircraft model that flies most regularly on the Islip to Boston flight route.

  • On which days can I fly direct from Islip to Boston?

    There are nonstop flights from Islip to Boston on a daily basis.

  • Which is the best airline for flights from Islip to Boston, Cape Air or Southwest?

    The two airlines most popular with KAYAK users for flights from Islip to Boston are Cape Air and Southwest. With an average price for the route of $520 and an overall rating of 9.3, Cape Air is the most popular choice. Southwest is also a great choice for the route, with an average price of $346 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Islip to Boston?

    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 Boston.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Boston from Islip 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 Boston?

    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 to Boston with an airline and back to Islip with another airline. Booking your flights between Islip and BOS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Islip to Boston?

    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 to Boston from Islip up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Islip to Boston

  • Looking for a cheap flight? 25% of our users found flights on this route for $570 or less round-trip.

Prefer to fly direct from Islip to Boston?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Islip Long Island to Boston Logan Intl.
Find which airlines fly direct from Islip Long Island Airport to Boston Logan Intl Airport, which days they fly and book direct flights.

Direct departures

Islip Long Island to Boston Logan Intl

Monday

Cape Air

Cape Air

Tuesday

Cape Air

Cape Air

Wednesday

Cape Air

Cape Air

Thursday

Cape Air

Cape Air

Friday

Cape Air

Cape Air

Saturday

Cape Air

Cape Air

Sunday

Cape Air

Cape Air

See more direct flights

Direct returns

Boston Logan Intl to Islip Long Island

Monday

Cape Air

Cape Air

Tuesday

Cape Air

Cape Air

Wednesday

Cape Air

Cape Air

Thursday

Cape Air

Cape Air

Friday

Cape Air

Cape Air

Saturday

Cape Air

Cape Air

Sunday

Cape Air

Cape Air

See more direct flights

Reviews of the top 3 airlines serving from Islip to Boston

 
See real verified KAYAK customer reviews for airlines flying from Islip to Boston. 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 Boston? 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
9.5Crew
8.7Comfort
9.0Entertainment
8.8Food
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.

Snacks are always pretzels. Why can't you also offer peanuts ?

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.

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.

we were delayed because of some safety check that wasn't done or available

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

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

Information on your arrival and departure airports