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$458+ Cheap flights from Islip, NY to Oakland, CA (ISP - OAK)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — OAK
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Islip to Oakland

Cheapest flights from Islip to Oakland
Explore the most affordable flight options available from Islip to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This Southwest deal was found by Cheapflights users on 2/12. 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 4/1412:30 pm
ISP
-
OAK
2 stops10h 50m
Southwest
Sun 4/1911:55 pm
OAK
-
ISP
2 stops8h 55m
Southwest
Deal found 2/12$458
This Southwest deal was found by Cheapflights users on 2/9. 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.
Tue 2/246:00 am
ISP
-
OAK
2 stops12h 30m
Southwest
Wed 3/49:20 am
OAK
-
ISP
2 stops9h 35m
Southwest
Deal found 2/9$552
This Southwest deal was found by Cheapflights users on 2/12. 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 3/52:00 pm
ISP
-
OAK
2 stops11h 25m
Southwest
Mon 3/910:00 am
OAK
-
ISP
2 stops10h 55m
Southwest
Deal found 2/12$577
This Southwest deal was found by Cheapflights users on 2/10. 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.
Fri 5/2912:30 pm
ISP
-
OAK
2 stops11h 15m
Southwest
Sun 5/319:55 am
OAK
-
ISP
2 stops10h 55m
Southwest
Deal found 2/10$583
This Southwest deal was found by Cheapflights users on 2/12. 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 3/2911:45 am
ISP
-
OAK
2 stops12h 20m
Southwest
Sun 4/511:25 am
OAK
-
ISP
2 stops9h 25m
Southwest
Deal found 2/12$984

Find flight deals from Islip to Oakland

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) to Oakland (OAK). 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 13, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$458
(Southwest)

Popular in

December

Cheapest in

January

Average price

$373
Provider with most accurate pricing for Islip Long Island-Oakland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Islip Long Island-Oakland flights.
Search Deals
From Islip Long Island to Oakland
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Oakland 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 13, 2026.
Use the filters below to find and compare flights from Islip to Oakland that are best for you.

Fly from

Islip

Fly to

Oakland

Route

Depart

Return

Price

IslipOakland

ISP - OAK

ISPOAK

Islip Long Island

Tue 4/14

12:30 pm-8:20 pm

2 stops10h 50m

Oakland

Sun 4/19

11:55 pm-11:50 am

2 stops8h 55m

$458

IslipOakland

ISP - OAK

ISPOAK

Islip Long Island

Tue 2/24

6:00 am-3:30 pm

2 stops12h 30m

Oakland

Wed 3/4

9:20 am-9:55 pm

2 stops9h 35m

$552

IslipOakland

ISP - OAK

ISPOAK

Islip Long Island

Thu 3/5

2:00 pm-10:25 pm

2 stops11h 25m

Oakland

Mon 3/9

10:00 am-11:55 pm

2 stops10h 55m

$577

IslipOakland

ISP - OAK

ISPOAK

Islip Long Island

Fri 5/29

12:30 pm-8:45 pm

2 stops11h 15m

Oakland

Sun 5/31

9:55 am-11:50 pm

2 stops10h 55m

$583

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

  • Most accurate provider: When it comes to deals on Islip, New York-Oakland, California flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Islip, New York-Oakland, California flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Islip, New York-Oakland, California flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Islip, New York-Oakland, California flights, Cheapflights users trust Expedia the most. Expedia 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-Oakland, California 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 Oakland

Have a flexible travel schedule? Discover the best time to fly to Oakland 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 Oakland

What is the cheapest month to book a flight from Islip, New York to Oakland, California?

Currently, December is the cheapest month in which you can book a flight from Islip, New York to Oakland, California (average of $113). Flying from Islip, New York to Oakland, California in July is currently the most expensive (average of $190). 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.

Related info for your journey

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

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

    Airlines like Southwest fly from Islip, New York to Oakland, California in about 12h 30m. The time it takes to get you to your destination can typically vary by up to . Islip, New York and Oakland, California are separated by a distance of 2601 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Islip to Oakland 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 Oakland, California?

    Currently, December is the cheapest month in which you can book a flight from Islip, New York to Oakland, California (average of $113). Flying from Islip, New York to Oakland, California in July is currently the most expensive (average of $190). 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

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