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Stewart

$181+ Cheap flights from Oakland, CA to New Windsor (OAK - SWF)

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SWF
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
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Cheap flight deals from Oakland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Stewart (SWF). 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 August 14, 2025.

Popular in

December

Cheapest in

February

Average price

$421
Highest demand for flights based on searches. 7% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Oakland to Stewart

One-way flights from Oakland to Stewart
Search for one-way flight options from Oakland to Stewart. Find affordable one-way fares based on user searches. Data last updated August 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amOAK - SWF
3 stops25h 51mMultiple Airlines
Deal found 8/12$181
This Kiwi.com deal was found by Cheapflights users on 8/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/42:39 pmOAK - SWF
3 stops23h 16mMultiple Airlines
Deal found 8/12$264
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 8/276:00 amOAK - SWF
3 stops50h 27mMultiple Airlines
Deal found 8/13$303
This Mytrip deal was found by Cheapflights users on 8/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/218:13 amOAK - SWF
3 stops29h 33mMultiple Airlines
Deal found 8/11$321
This Mytrip deal was found by Cheapflights users on 8/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/318:13 amOAK - SWF
3 stops25h 52mMultiple Airlines
Deal found 8/11$346
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Thu 8/286:00 amOAK - SWF
2 stops28h 05mMultiple Airlines
Deal found 8/13$350
This Kiwi.com deal was found by Cheapflights users on 8/13. 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 8/266:00 amOAK - SWF
3 stops50h 23mMultiple Airlines
Deal found 8/13$364
This Kiwi.com deal was found by Cheapflights users on 8/13. 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.
Sat 9/62:39 pmOAK - SWF
3 stops19h 35mMultiple Airlines
Deal found 8/13$369
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/76:30 amOAK - SWF
3 stops26h 14mMultiple Airlines
Deal found 8/11$377

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Stewart 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 August 14, 2025.
Use the filters below to find and compare flights from Oakland to New Windsor that are best for you.

Fly from

Oakland

Fly to

Stewart

Route

Depart

Return

Price

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Thu 10/2

6:30 am-11:21 am

3 stops25h 51m

$181

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sat 10/4

2:39 pm-10:11 am

3 stops40h 32m

$190

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sat 10/11

6:00 am-6:21 pm

3 stops33h 21m

$273

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Wed 8/27

6:00 am-11:27 am

3 stops50h 27m

$303

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sun 8/24

6:00 am-4:46 pm

3 stops31h 46m

$308

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Thu 8/21

8:13 am-4:46 pm

3 stops29h 33m

$321

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Fri 10/10

6:00 am-11:03 am

3 stops50h 03m

$332

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sun 8/31

8:13 am-1:05 pm

3 stops25h 52m

$346

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Best time to book a flight from Oakland to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Oakland 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 Oakland to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Oakland, California to New Windsor (average of $109). Flying from Oakland, California to New Windsor in December is currently the most expensive (average of $202). 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 Oakland to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Oakland to Stewart 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 Oakland, California to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Oakland, California to New Windsor (average of $109). Flying from Oakland, California to New Windsor in December is currently the most expensive (average of $202). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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