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$98+ Cheap flights from New Windsor to Cleveland (SWF - CLE)

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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CLE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Stewart to Cleveland

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Cleveland (CLE). 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

$201
(Kiwi.com)

One-way from

$98
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$219
From New Windsor Stewart to Cleveland Hopkins Intl
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One-way flight from New Windsor Stewart to Cleveland Hopkins Intl
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Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Cleveland

Cheapest flights from Stewart to Cleveland
Explore the most affordable flight options available from Stewart to Cleveland. 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 10/27:11 pmSWF - CLE
1 stop17h 22mMultiple Airlines
Sun 10/57:56 pmCLE - SWF
1 stop14h 15mMultiple Airlines
Deal found 9/9$201
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.
Fri 10/312:11 pmSWF - CLE
1 stop10h 52mMultiple Airlines
Sun 10/57:56 pmCLE - SWF
1 stop14h 15mMultiple Airlines
Deal found 9/9$206
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.
Sun 10/57:11 pmSWF - CLE
1 stop17h 22mMultiple Airlines
Thu 10/167:56 pmCLE - SWF
1 stop14h 45mMultiple Airlines
Deal found 9/9$234
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.
Fri 10/2411:31 amSWF - CLE
1 stop10h 28mMultiple Airlines
Sun 10/269:38 pmCLE - SWF
1 stop16h 33mMultiple Airlines
Deal found 9/10$238
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.
Sun 10/57:11 pmSWF - CLE
1 stop17h 22mMultiple Airlines
Sun 10/127:56 pmCLE - SWF
1 stop14h 15mMultiple Airlines
Deal found 9/9$246
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.
Mon 10/2011:01 amSWF - CLE
2 stops11h 08mMultiple Airlines
Thu 10/237:56 pmCLE - SWF
1 stop14h 45mMultiple Airlines
Deal found 9/9$248
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.
Fri 10/1011:41 amSWF - CLE
1 stop10h 18mMultiple Airlines
Sun 10/127:56 pmCLE - SWF
1 stop14h 15mMultiple Airlines
Deal found 9/10$259
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.
Fri 10/312:11 pmSWF - CLE
1 stop10h 52mMultiple Airlines
Thu 10/97:56 pmCLE - SWF
1 stop14h 55mMultiple Airlines
Deal found 9/9$262
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.
Mon 10/1311:01 amSWF - CLE
1 stop10h 58mMultiple Airlines
Thu 10/167:56 pmCLE - SWF
1 stop14h 45mMultiple Airlines
Deal found 9/10$286
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.
Fri 10/1711:31 amSWF - CLE
1 stop10h 52mMultiple Airlines
Mon 10/205:35 amCLE - SWF
2 stops11h 53mMultiple Airlines
Deal found 9/10$351

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Cleveland 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 New Windsor to Cleveland that are best for you.

Fly from

Stewart

Fly to

Cleveland

Route

Depart

Return

Price

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 10/2

7:11 pm-12:33 pm

1 stop17h 22m

Cleveland Hopkins Intl

Sun 10/5

7:56 pm-10:11 am

1 stop14h 15m

$201

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/3

12:11 pm-11:03 pm

1 stop10h 52m

Cleveland Hopkins Intl

Sun 10/5

7:56 pm-10:11 am

1 stop14h 15m

$201

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/31

11:31 am-8:33 pm

1 stop9h 02m

Cleveland Hopkins Intl

Sun 11/2

9:38 pm-11:11 am

1 stop13h 33m

$234

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 10/5

7:11 pm-12:33 pm

1 stop17h 22m

Cleveland Hopkins Intl

Thu 10/16

7:56 pm-10:41 am

1 stop14h 45m

$234

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/24

11:31 am-9:59 pm

1 stop10h 28m

Cleveland Hopkins Intl

Sun 10/26

9:38 pm-2:11 pm

1 stop16h 33m

$238

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 10/5

7:11 pm-12:33 pm

1 stop17h 22m

Cleveland Hopkins Intl

Sun 10/12

7:56 pm-10:11 am

1 stop14h 15m

$246

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 10/20

11:01 am-10:09 pm

2 stops11h 08m

Cleveland Hopkins Intl

Thu 10/23

7:56 pm-10:41 am

1 stop14h 45m

$248

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/10

11:41 am-9:59 pm

1 stop10h 18m

Cleveland Hopkins Intl

Sun 10/12

7:56 pm-10:11 am

1 stop14h 15m

$259

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 10/13

11:01 am-9:59 pm

1 stop10h 58m

Cleveland Hopkins Intl

Thu 10/16

7:56 pm-10:41 am

1 stop14h 45m

$286

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 10/23

7:11 pm-10:09 pm

1 stop26h 58m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 17 results
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Best time to book a flight from Stewart to Cleveland

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

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

Currently, April is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $250). Flying from New Windsor to Cleveland in June is currently the most expensive (average of $290). 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 Stewart to Cleveland. 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 Stewart to Cleveland that include hotel bookings?

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $250). Flying from New Windsor to Cleveland in June is currently the most expensive (average of $290). 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 Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Sandusky
Mentor
Beachwood
Wooster
Avon
Mansfield
Independence
Willoughby
Elyria
Streetsboro
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Strongsville
Kent
Medina
Westlake

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