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$109+ 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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CLE
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$275
(Kiwi.com)

One-way from

$109
(Kiwi.com)

Popular in

November

Cheapest in

February

Average price

$302
Provider with most accurate pricing for New Windsor Stewart-Cleveland Hopkins Intl flight deals.
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Provider most trusted by Cheapflights users for New Windsor Stewart-Cleveland Hopkins Intl flights.
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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. 18% potential increase in price ($51 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 November 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 November 13, 2025.

This Mytrip deal was found by Cheapflights users on 11/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1712:01 pmSWF - CLE
1 stop11h 58mMultiple Airlines
Thu 11/209:07 pmCLE - SWF
1 stop13h 15mMultiple Airlines
Deal found 11/11$241
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/315:34 pmSWF - CLE
1 stop14h 09mMultiple Airlines
Sun 1/46:59 pmCLE - SWF
1 stop17h 03mMultiple Airlines
Deal found 11/12$275
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/2912:52 pmSWF - CLE
1 stop18h 51mMultiple Airlines
Sun 1/46:59 pmCLE - SWF
1 stop17h 03mMultiple Airlines
Deal found 11/12$353
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 11/2011:43 amSWF - CLE
1 stop11h 43mMultiple Airlines
Sat 11/227:51 pmCLE - SWF
2 stops38h 16mMultiple Airlines
Deal found 11/12$370
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/209:45 amSWF - CLE
1 stop14h 06mMultiple Airlines
Tue 12/235:40 amCLE - SWF
1 stop10h 20mMultiple Airlines
Deal found 11/12$375
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/315:34 pmSWF - CLE
1 stop14h 09mMultiple Airlines
Sat 1/310:00 pmCLE - SWF
1 stop11h 59mMultiple Airlines
Deal found 11/12$408
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/2912:52 pmSWF - CLE
1 stop10h 59mMultiple Airlines
Wed 12/314:48 pmCLE - SWF
1 stop18h 15mMultiple Airlines
Deal found 11/12$439
This Kiwi.com deal was found by Cheapflights users on 11/12. 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 12/3011:43 amSWF - CLE
1 stop20h 00mMultiple Airlines
Sun 1/46:59 pmCLE - SWF
1 stop17h 03mMultiple Airlines
Deal found 11/12$450

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 November 13, 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

Wed 12/31

5:34 pm-7:43 am

1 stop14h 09m

Cleveland Hopkins Intl

Sun 1/4

6:59 pm-12:02 pm

1 stop17h 03m

$275

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sat 12/20

9:45 am-11:51 pm

1 stop14h 06m

Cleveland Hopkins Intl

Tue 12/23

5:40 am-4:00 pm

1 stop10h 20m

$375

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Wed 12/31

5:34 pm-7:43 am

1 stop14h 09m

Cleveland Hopkins Intl

Sat 1/3

10:00 pm-9:59 am

1 stop11h 59m

$408

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 1/1

11:43 am-11:51 pm

1 stop12h 08m

Cleveland Hopkins Intl

Sun 1/4

6:59 pm-11:44 am

2 stops16h 45m

$428

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 12/29

12:52 pm-11:51 pm

1 stop10h 59m

Cleveland Hopkins Intl

Wed 12/31

4:48 pm-11:03 am

1 stop18h 15m

$439

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Tue 12/30

11:43 am-7:43 am

1 stop20h 00m

Cleveland Hopkins Intl

Sun 1/4

6:59 pm-12:02 pm

1 stop17h 03m

$450

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 12/22

8:25 pm-11:59 pm

1 stop27h 34m

Cleveland Hopkins Intl

Sat 12/27

10:00 pm-9:59 am

1 stop11h 59m

$454

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 12/29

12:52 pm-7:43 am

1 stop18h 51m

Cleveland Hopkins Intl

Sat 1/3

10:00 pm-9:59 am

1 stop11h 59m

$486

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Wed 11/26

12:17 pm-11:26 pm

2 stops11h 09m

Cleveland Hopkins Intl

Sat 11/29

12:25 pm-9:22 am

1 stop20h 57m

$486

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Mon 12/29

12:52 pm-7:43 am

1 stop18h 51m

Cleveland Hopkins Intl

Thu 1/1

5:49 pm-7:28 pm

1 stop25h 39m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 20 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Cleveland flight deals on Cheapflights vs. eDreams >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 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 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, February is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $39). 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, February is the cheapest month in which you can book a flight from New Windsor to Cleveland (average of $39). 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
Mansfield
Avon
Beachwood
Wooster
Independence
Willoughby
Elyria
Streetsboro
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Kent
Strongsville
Medina
Lakewood
Westlake

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