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$140+ Cheap flights from Islip, NY to Boston (ISP - BOS)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — BOS
Jun 24 — Jul 11
Wed 6/24
Wed 7/1
1 adult, Economy
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Cheap flight deals from Islip to Boston

Cheapest flights from Islip to Boston
Explore the most affordable flight options available from Islip to Boston. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.

This Southwest deal was found by Cheapflights users on 5/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/165:55 pm
ISP
-
BOS
1 stop6h 30m
Southwest
Fri 10/235:35 am
BOS
-
ISP
1 stop6h 25m
Southwest
Deal found 5/23$347
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/255:50 pm
ISP
-
BOS
1 stop6h 15m
Southwest
Sun 6/289:40 pm
BOS
-
ISP
1 stop10h 40m
Southwest
Deal found 5/22$352
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/205:35 pm
ISP
-
BOS
1 stop6h 00m
Southwest
Sat 6/275:10 am
BOS
-
ISP
1 stop6h 25m
Southwest
Deal found 5/21$357
This Southwest deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/173:05 pm
ISP
-
BOS
2 stops9h 10m
Southwest
Sat 7/186:45 pm
BOS
-
ISP
1 stop4h 30m
Southwest
Deal found 5/24$362
This Southwest deal was found by Cheapflights users on 5/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/202:45 pm
ISP
-
BOS
1 stop3h 35m
Southwest
Mon 6/227:50 pm
BOS
-
ISP
1 stop3h 45m
Southwest
Deal found 5/22$367
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/176:00 am
ISP
-
BOS
1 stop6h 10m
Southwest
Wed 6/248:55 am
BOS
-
ISP
1 stop7h 05m
Southwest
Deal found 5/20$372
This Kiwi.com deal was found by Cheapflights users on 5/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:27 pm
ISP
-
BOS
1 stop17h 38m
Multiple Airlines
Fri 8/218:47 am
BOS
-
ISP
1 stop4h 41m
Multiple Airlines
Deal found 5/24$375
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/106:00 am
ISP
-
BOS
1 stop6h 10m
Southwest
Fri 6/127:50 pm
BOS
-
ISP
1 stop3h 45m
Southwest
Deal found 5/20$387
This Southwest deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1912:30 pm
ISP
-
BOS
1 stop4h 40m
Southwest
Sun 6/217:45 am
BOS
-
ISP
1 stop4h 00m
Southwest
Deal found 5/20$393

Find flight deals from Islip to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$347
(Southwest)

One-way from

$140
(Kiwi.com)

Popular in

November

Cheapest in

July

Average price

$598

Good round-trip deal

$530 or less

Good one-way deal

$249 or less
Provider with most accurate pricing for Islip Long Island-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Islip Long Island-Boston Logan Intl flights.
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From Islip Long Island to Boston Logan Intl
Search Deals
One-way flight from Islip Long Island to Boston Logan Intl
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals
Price to beat on a round-trip flight from Islip Long Island to Boston Logan Intl.
Search Deals
Price to beat on a one-way flight from Islip Long Island to Boston Logan Intl.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 25, 2026.
Use the filters below to find and compare flights from Islip to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 9/28

6:10 am-9:50 am

1 stop3h 40m

Boston Logan Intl

Fri 10/9

5:35 am-9:40 am

1 stop4h 05m

$347

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Wed 7/22

8:55 am-3:40 pm

1 stop6h 45m

Boston Logan Intl

Fri 7/24

7:50 pm-11:40 pm

1 stop3h 50m

$347

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 7/2

12:30 pm-5:10 pm

1 stop4h 40m

Boston Logan Intl

Sun 7/5

5:30 am-11:45 am

1 stop6h 15m

$347

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 9/7

6:10 am-12:30 pm

1 stop6h 20m

Boston Logan Intl

Tue 9/15

8:30 am-4:55 pm

2 stops8h 25m

$352

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 6/25

5:50 pm-12:05 am

1 stop6h 15m

Boston Logan Intl

Sun 6/28

9:40 pm-8:20 am

1 stop10h 40m

$352

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 7/13

12:30 pm-5:10 pm

1 stop4h 40m

Boston Logan Intl

Thu 7/16

7:50 pm-11:35 pm

1 stop3h 45m

$367

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Wed 6/17

6:00 am-12:10 pm

1 stop6h 10m

Boston Logan Intl

Wed 6/24

8:55 am-4:00 pm

1 stop7h 05m

$372

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Sat 6/20

12:15 pm-11:15 pm

2 stops11h 00m

Boston Logan Intl

Mon 6/22

5:45 am-11:50 am

1 stop6h 05m

$378

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Fri 6/19

12:30 pm-5:10 pm

1 stop4h 40m

Boston Logan Intl

Sun 6/21

7:45 am-11:45 am

1 stop4h 00m

$393

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 6/22

5:50 pm-9:40 pm

1 stop3h 50m

Boston Logan Intl

Mon 6/29

5:45 am-11:50 am

1 stop6h 05m

$398

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/23

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Compare providers for flights from Islip to Boston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Islip to Boston in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Islip, New York-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Islip, New York-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Islip, New York-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Boston flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Islip, New York-Boston flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Islip to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Islip with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest time of day to fly from ISP to BOS?

Find hourly flight availability from Islip to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 25, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Islip, New York to Boston as you normally would.

How much does it cost to fly round-trip from Islip, New York to Boston?

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated May 25, 2026.
See what other customers who have flown with Cape Air and Southwest from Islip to Boston have to say. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Cape Air
9.3
Wonderful
33 reviews

Comfort

8.6

Boarding

9.0

Overall

9.3

Crew

9.4

Entertainment

8.9

Food

8.7
Cape Air
9.3
Wonderful
33 reviews
Cape Air
9.3
Wonderful
33 reviews

Comfort

8.6

Boarding

9.0

Overall

9.3

Crew

9.4

Entertainment

8.9

Food

8.7
Southwest
7.9
Good
4,266 reviews
Cape Air
9.3
Wonderful
33 reviews

Comfort

8.6

Boarding

9.0

Overall

9.3

Crew

9.4

Entertainment

8.9

Food

8.7

Related info for your journey

Find useful and relevant information for your journey from Islip to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airports do I use to fly from Islip to Boston?

    If you book a flight from Islip to Boston, you will be flying from Long Island to Logan Intl. Flights to Boston Logan Intl (BOS) from Islip Long Island (ISP) take 1h 30m for a nonstop flight. There are 3 flights from Long Island to Boston per day from 2 airlines.

  • How long is the flight from Islip, New York to Boston?

    Airlines like Southwest fly from Islip, New York to Boston in about 3h 40m. The time it takes to get you to your destination can typically vary by up to . There are 153 mi between Islip, New York and Boston.

  • What are the cheapest airlines flying from Islip, New York to Boston round-trip?

    Our cheapest airline available from Islip, New York to Boston is Southwest. Our recent data shows that you can find tickets from as low as $174 on this airline. An additional option worth looking into is Cape Air, starting at $497. Users have found that Southwest is 66% cheaper than the other options available to this destination.

  • What are the cheapest flights from Islip, New York to Boston?

    On average you can expect to pay $410 for a flight from Islip, New York to Boston. The cheapest flight overall is $243 while the most popular route, (Islip Long Island - Boston Logan Intl) is currently priced at $347.

  • Can I find deals for flights from Islip to Boston that include hotel bookings?

    Yes. In addition to deals on Islip to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Islip to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Islip to Boston.

  • Can I find deals for business class flights from Islip to Boston?

    Yes. Cheapflights offers flight deals from Islip to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Waltham
Cambridge
Concord
Hampton Beach
Brockton
Watertown
Seekonk
Cranston
Chelsea
Warwick
Peabody
York Beach
Londonderry
Swansea
Old Orchard Beach
Auburn
Lowell
Smithfield
Braintree
Sandwich

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Islip to Boston

Discover the top 2 airlines that operate flights from Islip to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated May 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$174Average$387FlexibilityNo cancel feeOn-time63%
Cape AirCheapest$497Average$520FlexibilityNo cancel feeOn-time63%

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