HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$349+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SWF
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Oakland to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 29, 2025.

Most accurate provider

Expedia
2 stars

Most trusted provider

Expedia
3 stars

Popular in

December

Cheapest in

February

Average price

$402
Provider with most accurate pricing for Oakland-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Oakland-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/46:30 amOAK - SWF
3 stops48h 41mMultiple Airlines
Deal found 9/28$349
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/611:20 pmOAK - SWF
3 stops56h 43mMultiple Airlines
Deal found 9/28$389
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 10/810:00 pmOAK - SWF
3 stops33h 51mMultiple Airlines
Deal found 9/29$416
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 11/159:17 pmOAK - SWF
3 stops34h 54mMultiple Airlines
Deal found 9/27$424
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/1311:20 pmOAK - SWF
3 stops56h 43mMultiple Airlines
Deal found 9/28$425
This Kiwi.com deal was found by Cheapflights users on 9/28. 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 10/1511:20 pmOAK - SWF
3 stops32h 21mMultiple Airlines
Deal found 9/28$490
This Kiwi.com deal was found by Cheapflights users on 9/27. 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 10/1111:20 pmOAK - SWF
3 stops31h 51mMultiple Airlines
Deal found 9/27$559
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 10/2911:20 pmOAK - SWF
3 stops32h 21mMultiple Airlines
Deal found 9/26$580
This Kiwi.com deal was found by Cheapflights users on 9/29. 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 12/1912:30 pmOAK - SWF
3 stops43h 33mMultiple Airlines
Deal found 9/29$912

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 September 29, 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

Sat 10/4

6:30 am-10:11 am

3 stops48h 41m

$349

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Mon 10/6

11:20 pm-11:03 am

3 stops56h 43m

$389

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Wed 10/8

10:00 pm-10:51 am

3 stops33h 51m

$416

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sat 11/15

9:17 pm-11:11 am

3 stops34h 54m

$424

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Mon 10/13

11:20 pm-11:03 am

3 stops56h 43m

$425

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Wed 10/15

11:20 pm-10:41 am

3 stops32h 21m

$490

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Sat 10/11

11:20 pm-10:11 am

3 stops31h 51m

$559

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Wed 10/29

11:20 pm-10:41 am

3 stops32h 21m

$580

OaklandNew Windsor

OAK - SWF

OAKSWF

Oakland

Fri 12/19

12:30 pm-11:03 am

3 stops43h 33m

$912

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/28

  • 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Oakland to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
Los Angeles to Newark flights
San Francisco to Newark flights
Los Angeles to LaGuardia flights
San Francisco to LaGuardia flights
Ontario to John F Kennedy Intl flights
San Diego to John F Kennedy Intl flights
Santa Ana to Newark flights
Burbank to Newark flights
Santa Ana to LaGuardia flights
Burbank to LaGuardia flights
San Diego to Newark flights
Las Vegas to John F Kennedy Intl flights
Ontario to Newark flights
Santa Ana to John F Kennedy Intl flights
San Diego to LaGuardia flights
Ontario to LaGuardia flights
San Jose to John F Kennedy Intl flights
Las Vegas to Newark flights
San Jose to Newark flights
Sacramento to Newark flights
Las Vegas to LaGuardia flights
San Jose to LaGuardia flights
Oakland to Newark flights
Burbank to John F Kennedy Intl flights
Sacramento to John F Kennedy Intl flights
San Francisco to White Plains flights
Oakland to John F Kennedy Intl flights
Los Angeles to White Plains flights
Los Angeles to Islip flights
Sacramento to LaGuardia flights
San Jose to White Plains flights
Las Vegas to White Plains flights
Los Angeles to Buffalo flights
Palm Springs to John F Kennedy Intl flights
Fresno to John F Kennedy Intl flights
Long Beach to John F Kennedy Intl flights
Los Angeles to Albany flights
Palm Springs to Newark flights
Oakland to LaGuardia flights
Palm Springs to LaGuardia flights
Fresno to Newark flights
Reno to John F Kennedy Intl flights
San Francisco to Syracuse flights
Long Beach to Newark flights
Reno to Newark flights
San Francisco to Albany flights
Fresno to LaGuardia flights
San Francisco to Buffalo flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.