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$104+ 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 5/25. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CLE
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap 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 March 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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 5/259:41 am
SWF
-
CLE
1 stop21h 53m
Multiple Airlines
Thu 5/289:57 pm
CLE
-
SWF
1 stop10h 54m
Multiple Airlines
Deal found 3/26$236
This Kiwi.com deal was found by Cheapflights users on 3/25. 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 6/1012:05 pm
SWF
-
CLE
2 stops10h 30m
Multiple Airlines
Thu 6/119:42 pm
CLE
-
SWF
1 stop11h 07m
Multiple Airlines
Deal found 3/25$265
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/299:41 am
SWF
-
CLE
1 stop13h 30m
Multiple Airlines
Tue 6/26:33 pm
CLE
-
SWF
2 stops16h 52m
Multiple Airlines
Deal found 3/23$280
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/288:10 pm
SWF
-
CLE
1 stop28h 28m
Multiple Airlines
Tue 6/26:33 pm
CLE
-
SWF
2 stops16h 52m
Multiple Airlines
Deal found 3/23$288
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 8/279:38 am
SWF
-
CLE
1 stop10h 59m
Multiple Airlines
Sat 8/292:29 pm
CLE
-
SWF
1 stop18h 29m
Multiple Airlines
Deal found 3/23$298
This Kiwi.com deal was found by Cheapflights users on 3/27. 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.
Wed 5/612:05 pm
SWF
-
CLE
2 stops9h 46m
Multiple Airlines
Sat 5/99:57 pm
CLE
-
SWF
1 stop11h 01m
Multiple Airlines
Deal found 3/27$309
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Wed 5/2012:05 pm
SWF
-
CLE
2 stops9h 36m
Multiple Airlines
Sun 5/249:57 pm
CLE
-
SWF
1 stop10h 54m
Multiple Airlines
Deal found 3/26$311
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Tue 6/2311:48 am
SWF
-
CLE
1 stop10h 47m
Multiple Airlines
Fri 6/261:01 pm
CLE
-
SWF
1 stop22h 24m
Multiple Airlines
Deal found 3/24$320
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Tue 6/2311:48 am
SWF
-
CLE
1 stop10h 47m
Multiple Airlines
Sat 6/278:43 am
CLE
-
SWF
1 stop10h 27m
Multiple Airlines
Deal found 3/24$325
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Thu 6/49:38 am
SWF
-
CLE
1 stop11h 14m
Multiple Airlines
Sat 6/69:57 pm
CLE
-
SWF
1 stop11h 01m
Multiple Airlines
Deal found 3/24$332
This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Thu 4/2311:48 am
SWF
-
CLE
1 stop9h 07m
Multiple Airlines
Thu 4/3010:00 pm
CLE
-
SWF
1 stop12h 50m
Multiple Airlines
Deal found 3/26$333

Find 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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$236
(Kiwi.com)

One-way from

$104
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$243
Provider with most accurate pricing for New Windsor Stewart-Cleveland Hopkins Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Cleveland Hopkins Intl flights.
Search Deals
From New Windsor Stewart to Cleveland Hopkins Intl
Search Deals
One-way flight from New Windsor Stewart to Cleveland Hopkins Intl
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($55 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 March 2026
Search Deals

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 March 28, 2026.
Use the filters below to find and compare flights from New Windsor to Cleveland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 5/25

9:41 am-7:34 am

1 stop21h 53m

Cleveland Hopkins Intl

Thu 5/28

9:57 pm-8:51 am

1 stop10h 54m

$236

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 5/29

9:41 am-11:11 pm

1 stop13h 30m

Cleveland Hopkins Intl

Tue 6/2

6:33 pm-11:25 am

2 stops16h 52m

$280

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 5/28

8:10 pm-12:38 am

1 stop28h 28m

Cleveland Hopkins Intl

Tue 6/2

6:33 pm-11:25 am

2 stops16h 52m

$288

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Wed 5/6

12:05 pm-9:51 pm

2 stops9h 46m

Cleveland Hopkins Intl

Sat 5/9

9:57 pm-8:58 am

1 stop11h 01m

$309

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 6/4

9:38 am-8:52 pm

1 stop11h 14m

Cleveland Hopkins Intl

Sat 6/6

9:57 pm-8:58 am

1 stop11h 01m

$332

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 6/22

9:39 am-10:35 pm

1 stop12h 56m

Cleveland Hopkins Intl

Fri 6/26

1:01 pm-11:25 am

1 stop22h 24m

$333

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 6/25

10:28 am-9:57 pm

1 stop11h 29m

Cleveland Hopkins Intl

Fri 7/3

9:42 pm-5:54 pm

1 stop20h 12m

$337

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Fri 5/22

9:41 am-11:11 pm

1 stop13h 30m

Cleveland Hopkins Intl

Sun 5/24

9:57 pm-8:51 am

1 stop10h 54m

$338

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 6/25

10:28 am-9:57 pm

1 stop11h 29m

Cleveland Hopkins Intl

Tue 7/7

6:30 am-5:29 pm

1 stop10h 59m

$353
Quickest round-trip

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Wed 6/17

12:05 pm-5:02 pm

1 stop4h 57m

Cleveland Hopkins Intl

Sun 6/21

9:42 pm-8:49 am

1 stop11h 07m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/25

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

Compare providers for flights from Stewart to Cleveland

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 Stewart to Cleveland in March.
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 New Windsor-Cleveland flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Cleveland flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Cleveland flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Cleveland 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 New Windsor-Cleveland 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 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, November is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $54). Flying from New Windsor to Cleveland in June is currently the most expensive (average of $85). 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, November is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $54). Flying from New Windsor to Cleveland in June is currently the most expensive (average of $85). 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
Avon
Mansfield
Independence
Beachwood
Wooster
Strongsville
Lakewood
Streetsboro
Medina
North Olmsted
Cuyahoga Falls
Cleveland Heights
Macedonia
Kent
Elyria

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