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Stewart

$301+ Cheap flights from Hobby (HOU) to New Windsor (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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
HOU — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Hobby to Stewart

One-way flights from Hobby to Stewart
Search for one-way flight options from Hobby to Stewart. Find affordable one-way fares based on user searches. Data last updated January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/24. 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 5/257:39 pm
HOU
-
SWF
3 stops38h 46m
Multiple Airlines
Deal found 1/24$301
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 6/297:31 pm
HOU
-
SWF
2 stops20h 58m
Allegiant Air
Deal found 1/24$315
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 6/256:44 pm
HOU
-
SWF
3 stops39h 41m
Multiple Airlines
Deal found 1/25$323
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 6/267:31 pm
HOU
-
SWF
2 stops22h 39m
Allegiant Air
Deal found 1/24$327
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 6/286:44 pm
HOU
-
SWF
2 stops22h 52m
Allegiant Air
Deal found 1/25$333
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 7/27:03 pm
HOU
-
SWF
2 stops22h 48m
Allegiant Air
Deal found 1/25$351
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 6/256:44 pm
HOU
-
SWF
2 stops22h 52m
Allegiant Air
Deal found 1/25$383

Find flight deals from Hobby to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Hobby (HOU) 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 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

September

Average price

$207
Provider with most accurate pricing for Houston Hobby-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Houston Hobby-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hobby 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 26, 2026.
Use the filters below to find and compare flights from Houston Hobby Airport to New Windsor that are best for you.

Fly from

Hobby

Fly to

Stewart

Route

Depart

Return

Price

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Mon 5/25

7:39 pm-11:25 am

3 stops38h 46m

$301

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Mon 6/29

7:31 pm-5:29 pm

2 stops20h 58m

$315

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Thu 6/25

6:44 pm-11:25 am

3 stops39h 41m

$323

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Fri 6/26

7:31 pm-7:10 pm

2 stops22h 39m

$327

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Sun 6/28

6:44 pm-6:36 pm

2 stops22h 52m

$333

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Thu 7/2

7:03 pm-6:51 pm

2 stops22h 48m

$351

HoustonNew Windsor

HOU - SWF

HOUSWF

Houston Hobby

Thu 6/25

6:44 pm-6:36 pm

2 stops22h 52m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Compare providers for flights from Hobby to Stewart

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 Hobby to Stewart in January.
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 Houston Hobby Airport-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Houston Hobby Airport-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Houston Hobby Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Houston Hobby Airport-New Windsor 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 Houston Hobby Airport-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 Hobby to Stewart

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

What is the cheapest month to book a flight from Houston Hobby Airport to New Windsor?

Currently, March is the cheapest month in which you can book a flight from Houston Hobby Airport to New Windsor (average of $80). Flying from Houston Hobby Airport to New Windsor in July is currently the most expensive (average of $119). 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 Hobby to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Houston Hobby?

    New Windsor Stewart (SWF) is the airport you will fly into if you book a flight from Houston Hobby to New Windsor. You should not have trouble finding flights to Stewart from Houston Hobby; the airport handles an average of 0 inbound flights from Houston Hobby per day. You should also have plenty of airline options to choose from since 0 airlines have flights to the New Windsor airport from Houston Hobby. It is only a 4.3 mi journey from Stewart (SWF) to New Windsor’s city center.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Hobby 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 Houston Hobby Airport to New Windsor?

    Currently, March is the cheapest month in which you can book a flight from Houston Hobby Airport to New Windsor (average of $80). Flying from Houston Hobby Airport to New Windsor in July is currently the most expensive (average of $119). 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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