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Stewart

$97+ Cheap flights from Cleveland to New Windsor (CLE - SWF)

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
May 22 — May 291
Fri 5/22
Fri 5/29
1 adult, Economy
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Cheap flight deals from Cleveland to Stewart

Cheapest flights from Cleveland to Stewart
Explore the most affordable flight options available from Cleveland to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Tue 8/256:01 pm
CLE
-
SWF
2 stops17h 24m
Multiple Airlines
Sun 8/307:31 pm
SWF
-
CLE
1 stop26h 26m
Multiple Airlines
Deal found 4/19$226
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/289:57 pm
CLE
-
SWF
1 stop10h 54m
Multiple Airlines
Mon 6/19:41 am
SWF
-
CLE
1 stop11h 11m
Multiple Airlines
Deal found 4/20$257
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 7/14:05 pm
CLE
-
SWF
1 stop17h 33m
Multiple Airlines
Wed 7/87:46 pm
SWF
-
CLE
1 stop11h 52m
Multiple Airlines
Deal found 4/17$263
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Fri 8/281:01 pm
CLE
-
SWF
1 stop22h 24m
Multiple Airlines
Thu 9/37:30 pm
SWF
-
CLE
1 stop26h 27m
Multiple Airlines
Deal found 4/18$264
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 6/173:46 pm
CLE
-
SWF
2 stops17h 52m
Multiple Airlines
Sat 6/2012:05 pm
SWF
-
CLE
1 stop4h 58m
Multiple Airlines
Deal found 4/17$268
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Wed 5/279:57 pm
CLE
-
SWF
1 stop11h 01m
Multiple Airlines
Sat 5/3012:05 pm
SWF
-
CLE
1 stop5h 22m
Multiple Airlines
Deal found 4/18$272
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:57 pm
CLE
-
SWF
2 stops13h 28m
Multiple Airlines
Thu 5/79:38 am
SWF
-
CLE
1 stop11h 14m
Multiple Airlines
Deal found 4/20$293
This Kiwi.com deal was found by Cheapflights users on 4/18. 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.
Thu 6/189:42 pm
CLE
-
SWF
1 stop11h 07m
Multiple Airlines
Tue 6/2311:48 am
SWF
-
CLE
1 stop8h 49m
Multiple Airlines
Deal found 4/18$334
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Sat 7/183:46 pm
CLE
-
SWF
2 stops17h 52m
Multiple Airlines
Wed 7/2212:05 pm
SWF
-
CLE
1 stop4h 57m
Multiple Airlines
Deal found 4/19$345

Find flight deals from Cleveland to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Cleveland (CLE) to Stewart (SWF). 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 April 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$226
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$199
Provider with most accurate pricing for Cleveland Hopkins Intl-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Cleveland Hopkins Intl-New Windsor Stewart flights.
Search Deals
From Cleveland Hopkins Intl to New Windsor Stewart
Search Deals
One-way flight from Cleveland Hopkins Intl to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland to Stewart 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 April 22, 2026.
Use the filters below to find and compare flights from Cleveland to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 8/25

6:01 pm-11:25 am

2 stops17h 24m

New Windsor Stewart

Sun 8/30

7:31 pm-9:57 pm

1 stop26h 26m

$226

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 5/28

9:57 pm-8:51 am

1 stop10h 54m

New Windsor Stewart

Mon 6/1

9:41 am-8:52 pm

1 stop11h 11m

$257

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 7/1

4:05 pm-9:38 am

1 stop17h 33m

New Windsor Stewart

Wed 7/8

7:46 pm-7:38 am

1 stop11h 52m

$263

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 6/17

3:46 pm-9:38 am

2 stops17h 52m

New Windsor Stewart

Sat 6/20

12:05 pm-5:03 pm

1 stop4h 58m

$268

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 5/27

9:57 pm-8:58 am

1 stop11h 01m

New Windsor Stewart

Sat 5/30

12:05 pm-5:27 pm

1 stop5h 22m

$272

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 7/18

3:46 pm-9:38 am

2 stops17h 52m

New Windsor Stewart

Wed 7/22

12:05 pm-5:02 pm

1 stop4h 57m

$345
Quickest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 8/1

9:42 pm-8:58 am

1 stop11h 16m

New Windsor Stewart

Wed 8/5

12:05 pm-5:02 pm

1 stop4h 57m

$357

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 6/21

9:42 pm-8:49 am

1 stop11h 07m

New Windsor Stewart

Tue 6/23

11:48 am-8:37 pm

1 stop8h 49m

$359

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Tue 9/1

6:45 pm-11:25 am

2 stops16h 40m

New Windsor Stewart

Mon 9/7

12:16 pm-10:35 pm

1 stop10h 19m

$366

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 7/22

9:42 pm-8:58 am

1 stop11h 16m

New Windsor Stewart

Sat 7/25

12:05 pm-5:02 pm

1 stop4h 57m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/18

Showing 1-10 of 22 resultsSorted by cheapest first
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Compare providers for flights from Cleveland to Stewart

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 Cleveland to Stewart in April.
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 Cleveland-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Cleveland-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Cleveland-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Cleveland-New Windsor 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 Cleveland-New Windsor 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 Cleveland to Stewart

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

Related info for your journey

Find useful and relevant information for your journey from Cleveland to Stewart. 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 Cleveland to Stewart that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Cleveland to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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