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$108+ 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 4/19. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — BOS
Mar 27 — Apr 31
Fri 3/27
Fri 4/3
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 February 25, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1811:50 am
ISP
-
BOS
1 stop23h 50m
Multiple Airlines
Wed 3/255:49 pm
BOS
-
ISP
2 stops40h 24m
Multiple Airlines
Deal found 2/22$259
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/91:22 pm
ISP
-
BOS
2 stops22h 19m
Multiple Airlines
Fri 3/1312:56 pm
BOS
-
ISP
1 stop22h 14m
Multiple Airlines
Deal found 2/21$261
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/272:31 pm
ISP
-
BOS
1 stop20h 19m
Multiple Airlines
Sun 3/14:22 pm
BOS
-
ISP
1 stop15h 16m
Multiple Airlines
Deal found 2/20$277
This Southwest deal was found by Cheapflights users on 2/23. 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.
Wed 4/2212:30 pm
ISP
-
BOS
1 stop3h 25m
Southwest
Wed 4/225:25 pm
BOS
-
ISP
1 stop4h 45m
Southwest
Deal found 2/23$295
This Kiwi.com deal was found by Cheapflights users on 2/24. 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 3/2411:59 am
ISP
-
BOS
1 stop10h 30m
Multiple Airlines
Thu 3/2612:56 pm
BOS
-
ISP
1 stop24h 35m
Multiple Airlines
Deal found 2/24$320
This Kiwi.com deal was found by Cheapflights users on 2/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/710:03 am
ISP
-
BOS
1 stop13h 15m
Multiple Airlines
Tue 6/910:12 am
BOS
-
ISP
1 stop6h 35m
Multiple Airlines
Deal found 2/23$326
This Southwest deal was found by Cheapflights users on 2/21. 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 6/612:15 pm
ISP
-
BOS
1 stop6h 05m
Southwest
Sat 6/134:50 pm
BOS
-
ISP
1 stop6h 20m
Southwest
Deal found 2/21$327
This Southwest deal was found by Cheapflights users on 2/22. 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.
Sun 6/76:00 am
ISP
-
BOS
1 stop3h 50m
Southwest
Tue 6/911:35 am
BOS
-
ISP
1 stop4h 25m
Southwest
Deal found 2/22$337
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:20 pm
ISP
-
BOS
1 stop27h 09m
Multiple Airlines
Mon 3/303:00 pm
BOS
-
ISP
1 stop20h 14m
Multiple Airlines
Deal found 2/21$339

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 February 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

November

Cheapest in

May

Average price

$277
Provider with most accurate pricing for Islip Long Island-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Boston Logan Intl flights.
Search Deals
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. 24% potential increase in price ($134 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($21 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 25, 2026.
Use the filters below to find and compare flights from Islip to Boston that are best for you.

Fly from

Islip

Fly to

Boston

Route

Depart

Return

Price

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 3/9

1:22 pm-11:41 am

2 stops22h 19m

Boston Logan Intl

Fri 3/13

12:56 pm-11:10 am

1 stop22h 14m

$261

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Wed 3/18

11:50 am-11:40 am

1 stop23h 50m

Boston Logan Intl

Wed 3/25

4:23 pm-4:13 pm

1 stop23h 50m

$265

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Wed 4/22

12:30 pm-3:55 pm

1 stop3h 25m

Boston Logan Intl

Wed 4/22

5:25 pm-10:10 pm

1 stop4h 45m

$295

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 5/14

5:25 pm-12:09 am

1 stop6h 44m

Boston Logan Intl

Wed 5/20

10:36 am-7:39 pm

1 stop9h 03m

$373

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Tue 3/10

5:45 am-10:50 am

1 stop5h 05m

Boston Logan Intl

Wed 3/11

12:00 pm-4:05 pm

1 stop4h 05m

$429

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 4/2

10:31 am-10:43 am

1 stop24h 12m

Boston Logan Intl

Sun 4/5

11:31 am-9:28 am

1 stop21h 57m

$467

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 4/2

5:55 pm-12:05 am

1 stop6h 10m

Boston Logan Intl

Thu 4/16

7:25 pm-11:30 pm

1 stop4h 05m

$478

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 3/5

9:59 am-11:24 am

Nonstop1h 25m

Boston Logan Intl

Sun 3/8

12:50 pm-10:03 am

2 stops21h 13m

$508

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Fri 2/27

8:33 am-9:19 am

2 stops24h 46m

Boston Logan Intl

Sun 3/1

4:22 pm-2:39 pm

1 stop22h 17m

$518

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 5/14

7:25 am-8:59 am

Nonstop1h 34m

Boston Logan Intl

Wed 5/20

6:19 pm-7:45 pm

Nonstop1h 26m

$580

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 21 results
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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 February.
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 month to book a flight from Islip, New York to Boston?

Currently, May is the cheapest month in which you can book a flight from Islip, New York to Boston (average of $70). Flying from Islip, New York to Boston in September is currently the most expensive (average of $120). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 February 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.

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 February 25, 2026.
See what other customers who have flown with Cape Air, Southwest, and JetBlue 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
36 reviews

Comfort

8.7

Boarding

9.1

Overall

9.3

Crew

9.5

Entertainment

9.0

Food

8.8
Cape Air
9.3
Wonderful
36 reviews
Cape Air
9.3
Wonderful
36 reviews

Comfort

8.7

Boarding

9.1

Overall

9.3

Crew

9.5

Entertainment

9.0

Food

8.8
Southwest
8.0
Very good
4,300 reviews
Cape Air
9.3
Wonderful
36 reviews

Comfort

8.7

Boarding

9.1

Overall

9.3

Crew

9.5

Entertainment

9.0

Food

8.8
JetBlue
7.2
Good
2,897 reviews
Cape Air
9.3
Wonderful
36 reviews

Comfort

8.7

Boarding

9.1

Overall

9.3

Crew

9.5

Entertainment

9.0

Food

8.8

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 25m for a nonstop flight. There is 1 flight from Long Island to Boston per day from 3 airlines.

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

    Airlines like Southwest and JetBlue fly from Islip, New York to Boston in about 3h 25m. The time it takes to get you to your destination can typically vary by up to 3h 19m. There are 153 mi between Islip, New York and Boston. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 JetBlue. Our recent data shows that you can find tickets from as low as $97 on this airline. Additional options worth looking into are Southwest and Cape Air, starting at $280 and $475 round-trip. Users have found that JetBlue is 76% cheaper than the other options available to this destination.

  • 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.

  • What is the cheapest month to book a flight from Islip, New York to Boston?

    Currently, May is the cheapest month in which you can book a flight from Islip, New York to Boston (average of $70). Flying from Islip, New York to Boston in September is currently the most expensive (average of $120). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Medford
Cambridge
Hampton Beach
Watertown
Seekonk
Brockton
Concord
Seabrook
Cranston
Lincoln
Smithfield
Warwick
Peabody
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Lowell
Chelsea

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from Islip to Boston

Discover the top 3 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 February 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$97Average$187FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$280Average$346FlexibilityNo cancel feeOn-time63%
Cape AirCheapest$475Average$520FlexibilityNo cancel feeOn-time63%

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