HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$108+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$215
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$182
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. 12% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/167:56 pmCLE - SWF
1 stop14h 45mMultiple Airlines
Mon 10/2011:01 amSWF - CLE
1 stop14h 58mMultiple Airlines
Deal found 9/9$215
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Thu 10/309:38 pmCLE - SWF
1 stop13h 03mMultiple Airlines
Mon 11/312:01 pmSWF - CLE
1 stop8h 32mMultiple Airlines
Deal found 9/8$223
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 12/119:16 pmCLE - SWF
1 stop21h 24mMultiple Airlines
Sun 1/1111:48 amSWF - CLE
1 stop12h 38mMultiple Airlines
Deal found 9/10$334
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Thu 10/97:56 pmCLE - SWF
1 stop14h 55mMultiple Airlines
Thu 10/167:11 pmSWF - CLE
2 stops15h 36mMultiple Airlines
Deal found 9/11$346
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 9/242:00 pmCLE - SWF
1 stop21h 03mMultiple Airlines
Sun 9/2811:43 amSWF - CLE
1 stop29h 15mMultiple Airlines
Deal found 9/9$353
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 11/265:11 pmCLE - SWF
1 stop17h 52mMultiple Airlines
Mon 12/15:49 pmSWF - CLE
2 stops38h 19mMultiple Airlines
Deal found 9/8$515
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/254:52 pmCLE - SWF
1 stop18h 35mMultiple Airlines
Mon 12/15:49 pmSWF - CLE
2 stops45h 58mMultiple Airlines
Deal found 9/9$523
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/175:35 amCLE - SWF
2 stops12h 14mMultiple Airlines
Sun 10/1911:43 amSWF - CLE
1 stop13h 01mMultiple Airlines
Deal found 9/11$557
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/259:50 pmCLE - SWF
2 stops13h 54mMultiple Airlines
Sun 9/2811:43 amSWF - CLE
1 stop9h 08mMultiple Airlines
Deal found 9/10$601
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Sat 11/227:05 pmCLE - SWF
1 stop15h 11mMultiple Airlines
Mon 11/2412:24 pmSWF - CLE
2 stops11h 07mMultiple Airlines
Deal found 9/11$630
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/265:11 pmCLE - SWF
1 stop17h 52mMultiple Airlines
Sun 11/308:41 pmSWF - CLE
1 stop11h 24mMultiple Airlines
Deal found 9/9$669

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 September 11, 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

Thu 10/30

9:38 pm-10:41 am

1 stop13h 03m

New Windsor Stewart

Mon 11/3

12:01 pm-8:33 pm

1 stop8h 32m

$215

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 12/11

9:16 pm-6:40 pm

1 stop21h 24m

New Windsor Stewart

Sun 1/11

11:48 am-12:26 am

1 stop12h 38m

$334

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 10/9

7:56 pm-10:51 am

1 stop14h 55m

New Windsor Stewart

Thu 10/16

7:11 pm-10:47 am

2 stops15h 36m

$346

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 11/25

4:52 pm-11:27 am

1 stop18h 35m

New Windsor Stewart

Mon 12/1

5:49 pm-3:47 pm

2 stops45h 58m

$523

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Fri 10/17

5:35 am-5:49 pm

2 stops12h 14m

New Windsor Stewart

Sun 10/19

11:43 am-12:44 am

1 stop13h 01m

$557

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 9/25

9:50 pm-11:44 am

2 stops13h 54m

New Windsor Stewart

Sun 9/28

11:43 am-8:51 pm

1 stop9h 08m

$601

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 11/22

7:05 pm-10:16 am

1 stop15h 11m

New Windsor Stewart

Mon 11/24

12:24 pm-11:31 pm

2 stops11h 07m

$630

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 11/26

5:11 pm-11:03 am

1 stop17h 52m

New Windsor Stewart

Sun 11/30

8:41 pm-8:05 am

1 stop11h 24m

$669

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 10/2

9:50 pm-11:44 am

2 stops13h 54m

New Windsor Stewart

Sun 10/5

11:43 am-8:55 pm

1 stop9h 12m

$758

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Fri 12/19

8:05 am-6:06 pm

1 stop10h 01m

New Windsor Stewart

Mon 12/22

12:24 pm-10:51 pm

2 stops10h 27m

$882

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 20 results
1
2

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, October is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $109). Flying from Cleveland 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 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, October is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $109). Flying from Cleveland 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 Cleveland to Stewart

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