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Stewart

$373+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SWF
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Popular in

December

Cheapest in

February

Average price

$338
Provider with most accurate pricing for Oakland-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Oakland-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/5. 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 2/185:31 pmOAK - SWF
3 stops37h 43mMultiple Airlines
Deal found 1/5$373
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:10 amOAK - SWF
3 stops47h 04mMultiple Airlines
Deal found 1/8$492
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 2/207:32 pmOAK - SWF
3 stops36h 36mMultiple Airlines
Deal found 1/6$495
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1311:05 pmOAK - SWF
3 stops32h 47mMultiple Airlines
Deal found 1/8$510
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 1/1511:05 pmOAK - SWF
3 stops57h 28mMultiple Airlines
Deal found 1/6$601
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 4/107:00 amOAK - SWF
3 stops48h 55mMultiple Airlines
Deal found 1/6$602
This Kiwi.com deal was found by Cheapflights users on 1/5. 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 1/131:25 pmOAK - SWF
3 stops43h 08mMultiple Airlines
Deal found 1/5$700

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 January 8, 2026.
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

Wed 2/18

5:31 pm-10:14 am

3 stops37h 43m

$373

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Wed 2/11

8:10 am-10:14 am

3 stops47h 04m

$492

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Fri 2/20

7:32 pm-11:08 am

3 stops36h 36m

$495

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Fri 2/13

11:05 pm-10:52 am

3 stops32h 47m

$510

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Thu 1/15

11:05 pm-11:33 am

3 stops57h 28m

$601

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Fri 4/10

7:00 am-10:55 am

3 stops48h 55m

$602

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Tue 1/13

1:25 pm-11:33 am

3 stops43h 08m

$700

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

  • Most accurate provider: When it comes to deals on Oakland, California-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Oakland, California-New Windsor flight deals on Cheapflights vs. Expedia 90-95% of the time. Price accuracy is based on data collected from Oakland, California-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-New Windsor 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 Oakland, California-New Windsor 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 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, February is the cheapest month in which you can book a flight from Oakland, California to New Windsor (average of $96). Flying from Oakland, California to New Windsor in June is currently the most expensive (average of $203). 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, February is the cheapest month in which you can book a flight from Oakland, California to New Windsor (average of $96). Flying from Oakland, California to New Windsor in June is currently the most expensive (average of $203). 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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