HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$84+ Cheap flights from Cleveland to New Windsor (CLE - 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 12/22. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
Nov 26 — Dec 31
Wed 11/26
Wed 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cleveland 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 Cleveland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) 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 October 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$418
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$215
Provider with most accurate pricing for Cleveland Hopkins Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-New Windsor Stewart flights.
Search Deals
From Cleveland Hopkins Intl to New Windsor Stewart
Search Deals
One-way flight from Cleveland Hopkins Intl to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 11% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Cleveland to Stewart

Cheapest flights from Cleveland to Stewart
Explore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sat 11/19:38 pmCLE - SWF
1 stop14h 25mMultiple Airlines
Mon 11/312:01 pmSWF - CLE
1 stop11h 10mMultiple Airlines
Deal found 10/25$271
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Mon 11/246:33 pmCLE - SWF
1 stop14h 20mMultiple Airlines
Thu 11/2711:43 amSWF - CLE
1 stop11h 43mMultiple Airlines
Deal found 10/25$418
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Sat 11/87:14 pmCLE - SWF
1 stop15h 49mMultiple Airlines
Mon 11/1012:01 pmSWF - CLE
1 stop9h 15mMultiple Airlines
Deal found 10/25$434
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Wed 10/294:15 pmCLE - SWF
2 stops18h 48mMultiple Airlines
Fri 10/3111:31 amSWF - CLE
1 stop11h 40mMultiple Airlines
Deal found 10/25$441
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:33 pmCLE - SWF
1 stop16h 30mMultiple Airlines
Mon 11/2410:57 amSWF - CLE
2 stops13h 57mMultiple Airlines
Deal found 10/27$497
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/117:17 pmCLE - SWF
2 stops16h 27mMultiple Airlines
Sun 12/1411:43 amSWF - CLE
1 stop11h 03mMultiple Airlines
Deal found 10/25$644
This Mytrip deal was found by Cheapflights users on 10/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/239:07 pmCLE - SWF
1 stop13h 00mMultiple Airlines
Sun 11/3010:12 amSWF - CLE
1 stop10h 00mMultiple Airlines
Deal found 10/26$724
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Mon 11/246:33 pmCLE - SWF
1 stop14h 20mMultiple Airlines
Sun 11/3010:12 amSWF - CLE
1 stop12h 12mMultiple Airlines
Deal found 10/26$735
This Kiwi.com deal was found by Cheapflights users on 10/25. 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.
Mon 11/246:33 pmCLE - SWF
1 stop14h 20mMultiple Airlines
Mon 12/112:24 pmSWF - CLE
2 stops11h 02mMultiple Airlines
Deal found 10/25$783

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland 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 October 27, 2025.
Use the filters below to find and compare flights from Cleveland to New Windsor that are best for you.

Fly from

Cleveland

Fly to

Stewart

Route

Depart

Return

Price

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 11/1

9:38 pm-12:03 pm

1 stop14h 25m

New Windsor Stewart

Mon 11/3

12:01 pm-11:11 pm

1 stop11h 10m

$271

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Mon 11/24

6:33 pm-8:53 am

1 stop14h 20m

New Windsor Stewart

Thu 11/27

11:43 am-11:26 pm

1 stop11h 43m

$418

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 11/8

7:14 pm-11:03 am

1 stop15h 49m

New Windsor Stewart

Mon 11/10

12:01 pm-9:16 pm

1 stop9h 15m

$434

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 11/22

6:33 pm-11:03 am

1 stop16h 30m

New Windsor Stewart

Mon 11/24

10:57 am-12:54 am

2 stops13h 57m

$497

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 12/11

7:17 pm-11:44 am

2 stops16h 27m

New Windsor Stewart

Sun 12/14

11:43 am-10:46 pm

1 stop11h 03m

$644

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Mon 11/24

6:33 pm-8:53 am

1 stop14h 20m

New Windsor Stewart

Sun 11/30

10:12 am-10:24 pm

1 stop12h 12m

$735

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Mon 11/24

6:33 pm-8:53 am

1 stop14h 20m

New Windsor Stewart

Mon 12/1

12:24 pm-11:26 pm

2 stops11h 02m

$783

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Mon 12/22

6:00 am-7:35 pm

1 stop13h 35m

$84

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 12/7

10:54 am-11:37 am

1 stop24h 43m

$100

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 11/20

9:07 pm-10:22 am

1 stop13h 15m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/25

Showing 1-10 of 18 results
1
2

Compare providers for flights from Cleveland 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 Cleveland to Stewart in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

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

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

What is the cheapest month to book a flight from Cleveland to New Windsor?

Currently, November is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $42). Flying from Cleveland to New Windsor in December is currently the most expensive (average of $77). 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 Cleveland 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 Cleveland to Stewart that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Cleveland 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 Cleveland to New Windsor?

    Currently, November is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $42). Flying from Cleveland to New Windsor in December is currently the most expensive (average of $77). 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 Cleveland to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Detroit to John F Kennedy Intl flights
Cleveland to John F Kennedy Intl flights
Cincinnati to LaGuardia flights
Cleveland to LaGuardia flights
Cincinnati to John F Kennedy Intl flights
Detroit to LaGuardia flights
Detroit to Newark flights
Columbus to John F Kennedy Intl flights
Cincinnati to Newark flights
Cleveland to Newark flights
Columbus to Newark flights
Pittsburgh to John F Kennedy Intl flights
Columbus to LaGuardia flights
Pittsburgh to LaGuardia flights
Pittsburgh to Newark flights
Akron to White Plains flights
Pittsburgh to Bradford flights
Detroit to Albany flights
Dayton to LaGuardia flights
Dayton to John F Kennedy Intl flights
Dayton to Newark flights
Akron to Newark flights
Cleveland to Islip flights
Cincinnati to Syracuse flights
Cincinnati to Stewart flights
Akron to LaGuardia flights
Cincinnati to Buffalo flights
Cincinnati to Islip flights
Akron to John F Kennedy Intl flights
Detroit to White Plains flights
Cincinnati to White Plains flights
Cincinnati to Ithaca flights
Cincinnati to Albany flights
Detroit to Stewart flights
Detroit to Rochester flights
Columbus to Albany flights
Detroit to Syracuse flights
Pittsburgh to Stewart flights
Pittsburgh to Albany flights
Cleveland to Albany flights
Pittsburgh to White Plains flights
Detroit to Buffalo flights
Columbus to White Plains flights
Cleveland to Syracuse flights
Cleveland to White Plains flights
Dayton to Albany flights
Columbus to Syracuse flights
Columbus to Stewart flights
Dayton to White Plains 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.