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$102+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CLE
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$209
(Mytrip)

One-way from

$102
(Mytrip)

Popular in

December

Cheapest in

February

Average price

$224
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. 10% 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 August 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 August 20, 2025.

This Mytrip deal was found by Cheapflights users on 8/20. 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.
Fri 10/2411:31 amSWF - CLE
1 stop9h 02mMultiple Airlines
Sun 10/269:38 pmCLE - SWF
1 stop16h 33mMultiple Airlines
Deal found 8/20$209
This Mytrip deal was found by Cheapflights users on 8/20. 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.
Fri 10/1011:41 amSWF - CLE
1 stop8h 52mMultiple Airlines
Sun 10/129:38 pmCLE - SWF
1 stop12h 33mMultiple Airlines
Deal found 8/20$217
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 10/611:01 amSWF - CLE
1 stop9h 32mMultiple Airlines
Thu 10/99:38 pmCLE - SWF
1 stop13h 13mMultiple Airlines
Deal found 8/18$226
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Fri 10/2411:31 amSWF - CLE
1 stop9h 02mMultiple Airlines
Sat 10/259:38 pmCLE - SWF
2 stops20h 43mMultiple Airlines
Deal found 8/18$251
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Mon 10/1311:01 amSWF - CLE
1 stop9h 32mMultiple Airlines
Thu 10/169:38 pmCLE - SWF
1 stop13h 03mMultiple Airlines
Deal found 8/18$259
This Mytrip deal was found by Cheapflights users on 8/18. 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.
Thu 10/25:45 pmSWF - CLE
1 stop15h 06mMultiple Airlines
Thu 10/99:38 pmCLE - SWF
1 stop13h 13mMultiple Airlines
Deal found 8/18$280
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/77:12 pmSWF - CLE
2 stops23h 12mMultiple Airlines
Fri 10/39:46 amCLE - SWF
1 stop8h 03mMultiple Airlines
Deal found 8/19$314
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/187:12 pmSWF - CLE
1 stop25h 12mMultiple Airlines
Thu 9/256:00 amCLE - SWF
1 stop12h 22mMultiple Airlines
Deal found 8/19$337

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 August 20, 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

Fri 10/24

11:31 am-8:33 pm

1 stop9h 02m

Cleveland Hopkins Intl

Sun 10/26

9:38 pm-2:11 pm

1 stop16h 33m

$209

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/10

11:41 am-8:33 pm

1 stop8h 52m

Cleveland Hopkins Intl

Sun 10/12

9:38 pm-10:11 am

1 stop12h 33m

$217

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 10/6

11:01 am-8:33 pm

1 stop9h 32m

Cleveland Hopkins Intl

Thu 10/9

9:38 pm-10:51 am

1 stop13h 13m

$226

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/24

11:31 am-8:33 pm

1 stop9h 02m

Cleveland Hopkins Intl

Sat 10/25

9:38 pm-6:21 pm

2 stops20h 43m

$251

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 10/13

11:01 am-8:33 pm

1 stop9h 32m

Cleveland Hopkins Intl

Thu 10/16

9:38 pm-10:41 am

1 stop13h 03m

$259

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 10/2

5:45 pm-8:51 am

1 stop15h 06m

Cleveland Hopkins Intl

Thu 10/9

9:38 pm-10:51 am

1 stop13h 13m

$280

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 9/7

7:12 pm-6:24 pm

2 stops23h 12m

Cleveland Hopkins Intl

Fri 10/3

9:46 am-5:49 pm

1 stop8h 03m

$314

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 10/20

11:01 am-8:33 pm

1 stop9h 32m

$102

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/17

11:31 am-8:33 pm

1 stop9h 02m

$102

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 10/10

11:41 am-8:33 pm

1 stop8h 52m

$106

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 14 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
Mansfield
Wooster
Avon
Independence
Willoughby
Elyria
Streetsboro
Kent
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Strongsville
Medina
Westlake

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