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$108+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — CLE
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Fri 1/3011:09 am
SWF
-
CLE
1 stop11h 35m
Multiple Airlines
Sun 2/13:04 pm
CLE
-
SWF
1 stop19h 15m
Multiple Airlines
Deal found 1/26$279
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 stops11h 09m
Multiple Airlines
Wed 5/275:35 pm
CLE
-
SWF
1 stop16h 03m
Multiple Airlines
Deal found 1/26$354
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 4/1611:48 am
SWF
-
CLE
1 stop9h 07m
Multiple Airlines
Wed 4/228:01 pm
CLE
-
SWF
1 stop15h 07m
Multiple Airlines
Deal found 1/27$524
This Kiwi.com deal was found by Cheapflights users on 1/26. 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
Sun 4/2610:00 pm
CLE
-
SWF
2 stops13h 31m
Multiple Airlines
Deal found 1/26$531
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 4/210:29 am
SWF
-
CLE
1 stop13h 07m
Multiple Airlines
Sat 4/46:26 pm
CLE
-
SWF
1 stop15h 13m
Multiple Airlines
Deal found 1/27$539
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Sun 3/298:40 pm
SWF
-
CLE
1 stop11h 20m
Multiple Airlines
Sun 4/126:52 pm
CLE
-
SWF
1 stop15h 58m
Multiple Airlines
Deal found 1/26$561
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 3/511:48 am
SWF
-
CLE
1 stop11h 21m
Multiple Airlines
Sun 3/810:00 pm
CLE
-
SWF
2 stops13h 31m
Multiple Airlines
Deal found 1/27$1,162

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$354
(Kiwi.com)

One-way from

$108
(Kiwi.com)

Popular in

December

Cheapest in

February

Average price

$237
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. 19% potential increase in price ($59 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 January 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 January 28, 2026.
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 5/20

12:05 pm-11:14 pm

2 stops11h 09m

Cleveland Hopkins Intl

Wed 5/27

5:35 pm-9:38 am

1 stop16h 03m

$354

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 4/16

11:48 am-8:55 pm

1 stop9h 07m

Cleveland Hopkins Intl

Wed 4/22

8:01 pm-11:08 am

1 stop15h 07m

$524

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 4/23

11:48 am-8:55 pm

1 stop9h 07m

Cleveland Hopkins Intl

Sun 4/26

10:00 pm-11:31 am

2 stops13h 31m

$531

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 4/2

10:29 am-11:36 pm

1 stop13h 07m

Cleveland Hopkins Intl

Sat 4/4

6:26 pm-9:39 am

1 stop15h 13m

$539

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 3/29

8:40 pm-8:00 am

1 stop11h 20m

Cleveland Hopkins Intl

Sun 4/12

6:52 pm-10:50 am

1 stop15h 58m

$561

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 3/5

11:48 am-11:09 pm

1 stop11h 21m

Cleveland Hopkins Intl

Sun 3/8

10:00 pm-11:31 am

2 stops13h 31m

$1,162

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 3/8

10:09 am-6:09 pm

1 stop32h 00m

$136

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Sun 3/15

12:29 pm-5:11 pm

1 stop28h 42m

$144

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 5/28

10:28 am-4:40 pm

1 stop30h 12m

$218

New WindsorCleveland

SWF - CLE

SWFCLE

New Windsor Stewart

Thu 3/26

10:29 am-1:42 am

1 stop15h 13m

$260

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 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 January.
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, 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
Independence
Wooster
Beachwood
Willoughby
Lakewood
Streetsboro
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Kent
Medina
Strongsville
Elyria

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