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$114+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — BOS
Aug 11 — Aug 181
Tue 8/11
Tue 8/18
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 July 12, 2026.

This Southwest deal was found by Cheapflights users on 7/9. 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 8/1912:55 pm
ISP
-
BOS
1 stop5h 40m
Southwest
Thu 8/205:50 am
BOS
-
ISP
1 stop3h 50m
Southwest
Deal found 7/9$228
This Southwest deal was found by Cheapflights users on 7/10. 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 8/276:10 am
ISP
-
BOS
1 stop3h 40m
Southwest
Tue 9/18:30 am
BOS
-
ISP
2 stops8h 25m
Southwest
Deal found 7/10$234
This Southwest deal was found by Cheapflights users on 7/9. 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 10/23:10 pm
ISP
-
BOS
1 stop4h 05m
Southwest
Mon 10/57:50 pm
BOS
-
ISP
1 stop3h 45m
Southwest
Deal found 7/9$258
This Southwest deal was found by Cheapflights users on 7/8. 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.
Tue 9/86:05 am
ISP
-
BOS
1 stop3h 25m
Southwest
Tue 9/222:45 pm
BOS
-
ISP
1 stop6h 20m
Southwest
Deal found 7/8$288
This Southwest deal was found by Cheapflights users on 7/9. 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 9/44:05 pm
ISP
-
BOS
1 stop6h 05m
Southwest
Tue 9/85:25 am
BOS
-
ISP
1 stop4h 50m
Southwest
Deal found 7/9$298
This Southwest deal was found by Cheapflights users on 7/10. 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.
Tue 8/2512:55 pm
ISP
-
BOS
2 stops8h 25m
Southwest
Thu 8/275:50 am
BOS
-
ISP
1 stop3h 50m
Southwest
Deal found 7/10$303
This Southwest deal was found by Cheapflights users on 7/7. 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.
Tue 8/410:55 am
ISP
-
BOS
1 stop5h 05m
Southwest
Tue 8/114:55 pm
BOS
-
ISP
1 stop4h 10m
Southwest
Deal found 7/7$308
This Southwest deal was found by Cheapflights users on 7/10. 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 10/2211:00 am
ISP
-
BOS
1 stop6h 20m
Southwest
Fri 10/232:35 pm
BOS
-
ISP
2 stops8h 35m
Southwest
Deal found 7/10$313
This Southwest deal was found by Cheapflights users on 7/9. 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 8/284:05 pm
ISP
-
BOS
1 stop6h 05m
Southwest
Sun 9/610:40 am
BOS
-
ISP
1 stop5h 55m
Southwest
Deal found 7/9$317
This Southwest deal was found by Cheapflights users on 7/10. 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.
Mon 8/33:05 pm
ISP
-
BOS
1 stop6h 35m
Southwest
Wed 8/55:25 am
BOS
-
ISP
1 stop4h 50m
Southwest
Deal found 7/10$320

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 July 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$228
(Southwest)

One-way from

$114
(Southwest)

Popular in

November

Cheapest in

June

Average price

$520

Good round-trip deal

$520 or less

Good one-way deal

$300 or less
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. 3% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 12, 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

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Tue 8/4

10:55 am-4:00 pm

1 stop5h 05m

Boston Logan Intl

Tue 8/11

4:55 pm-9:05 pm

1 stop4h 10m

$308

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 8/3

3:05 pm-9:40 pm

1 stop6h 35m

Boston Logan Intl

Wed 8/5

5:25 am-10:15 am

1 stop4h 50m

$320

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Mon 11/2

5:35 am-12:15 pm

1 stop6h 40m

Boston Logan Intl

Thu 11/5

11:45 am-5:05 pm

1 stop5h 20m

$347

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Fri 8/14

10:20 am-2:30 pm

1 stop4h 10m

Boston Logan Intl

Sun 8/16

5:55 am-9:55 am

1 stop4h 00m

$347

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Fri 10/2

3:10 pm-7:15 pm

1 stop4h 05m

Boston Logan Intl

Mon 10/5

2:35 pm-11:10 pm

2 stops8h 35m

$359

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Wed 8/5

3:20 pm-9:25 pm

1 stop6h 05m

Boston Logan Intl

Mon 8/10

5:50 am-9:40 am

1 stop3h 50m

$367

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Sun 8/9

6:20 am-12:40 pm

1 stop6h 20m

Boston Logan Intl

Sun 8/16

5:55 am-9:55 am

1 stop4h 00m

$383
Quickest round-trip

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Tue 8/4

6:05 am-9:30 am

1 stop3h 25m

Boston Logan Intl

Thu 8/6

5:50 am-9:40 am

1 stop3h 50m

$387

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Sun 8/2

6:00 am-9:50 am

1 stop3h 50m

Boston Logan Intl

Mon 8/10

5:50 am-9:40 am

1 stop3h 50m

$426
Cheapest one-way

IslipBoston

ISP - BOS

ISPBOS

Islip Long Island

Thu 8/27

6:10 am-9:50 am

1 stop3h 40m

$114

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 19 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 July.
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 July 12, 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 July 12, 2026.
See what other customers who have flown with Cape Air 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

Overall

9.3

Boarding

9.0

Entertainment

8.9

Food

8.7

Crew

9.4
Cape Air
9.3
Wonderful
33 reviews
Cape Air
9.3
Wonderful
33 reviews

Comfort

8.6

Overall

9.3

Boarding

9.0

Entertainment

8.9

Food

8.7

Crew

9.4

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 1 airline.

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

    Airlines like Southwest fly from Islip, New York to Boston in about 5h 05m. 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 is the cheapest airline to fly from Islip, New York to Boston round-trip?

    Our cheapest airline available from Islip, New York to Boston is Cape Air. Our recent data shows that you can find tickets from as low as $497 on this airline. Users have found that Cape Air is 7% 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 $448 for a flight from Islip, New York to Boston. The cheapest flight overall is $260 while the most popular route, (Islip Long Island - Boston Logan Intl) is currently priced at $228.

  • 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
Brockton
Hampton Beach
Seekonk
Cranston
Warwick
Dedham
Peabody
Randolph
Auburn
Fitchburg
York Beach
Chelsea
Londonderry
Swansea
North Falmouth
Smithfield
Braintree

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Islip to Boston

Discover the top airline 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 July 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Cape AirCheapest$497Average$520FlexibilityNo cancel feeOn-time63%

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