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Stewart

$103+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/26. 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 10/214:17 pm
CLE
-
SWF
1 stop17h 31m
Multiple Airlines
Sat 10/2412:39 pm
SWF
-
CLE
1 stop4h 38m
Multiple Airlines
Deal found 7/26$240
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 10/229:42 pm
CLE
-
SWF
1 stop19h 07m
Multiple Airlines
Sun 10/2511:58 am
SWF
-
CLE
1 stop11h 04m
Multiple Airlines
Deal found 7/27$265
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/38:10 am
CLE
-
SWF
1 stop10h 30m
Multiple Airlines
Sun 9/610:33 am
SWF
-
CLE
1 stop12h 17m
Multiple Airlines
Deal found 7/23$270
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Sat 8/84:05 pm
CLE
-
SWF
1 stop17h 33m
Multiple Airlines
Sun 8/307:31 pm
SWF
-
CLE
1 stop27h 58m
Multiple Airlines
Deal found 7/24$274
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 9/38:10 am
CLE
-
SWF
1 stop10h 30m
Multiple Airlines
Sat 9/512:05 pm
SWF
-
CLE
1 stop5h 10m
Multiple Airlines
Deal found 7/23$277
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Mon 8/319:47 pm
CLE
-
SWF
1 stop13h 21m
Multiple Airlines
Thu 9/37:30 pm
SWF
-
CLE
1 stop19h 30m
Multiple Airlines
Deal found 7/27$280
This Kiwi.com deal was found by Cheapflights users on 7/27. 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 8/269:47 pm
CLE
-
SWF
1 stop12h 06m
Multiple Airlines
Wed 9/212:05 pm
SWF
-
CLE
1 stop5h 10m
Multiple Airlines
Deal found 7/27$292
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
Tue 8/259:47 pm
CLE
-
SWF
2 stops13h 38m
Multiple Airlines
Tue 9/111:48 am
SWF
-
CLE
1 stop8h 54m
Multiple Airlines
Deal found 7/27$294
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Wed 8/194:38 pm
CLE
-
SWF
1 stop19h 32m
Multiple Airlines
Sat 8/2212:05 pm
SWF
-
CLE
1 stop5h 10m
Multiple Airlines
Deal found 7/23$296
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Mon 8/249:47 pm
CLE
-
SWF
1 stop13h 21m
Multiple Airlines
Thu 8/2710:33 am
SWF
-
CLE
1 stop10h 09m
Multiple Airlines
Deal found 7/24$310

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$240
(Kiwi.com)

One-way from

$103
(Kiwi.com)

Popular in

June

Cheapest in

May

Average price

$215
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
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 27, 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

Wed 8/19

4:38 pm-12:10 pm

1 stop19h 32m

New Windsor Stewart

Sat 8/22

12:05 pm-5:15 pm

1 stop5h 10m

$296
Quickest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 8/30

8:10 am-6:41 pm

1 stop10h 31m

New Windsor Stewart

Mon 8/31

11:10 am-8:42 pm

2 stops9h 32m

$330

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 8/27

9:47 pm-10:06 am

1 stop12h 19m

New Windsor Stewart

Sun 8/30

7:31 pm-3:00 pm

1 stop19h 29m

$343

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Mon 8/24

9:47 pm-11:08 am

1 stop13h 21m

New Windsor Stewart

Sun 8/30

10:33 am-8:42 pm

1 stop10h 09m

$345

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 8/12

4:05 pm-9:38 am

1 stop17h 33m

New Windsor Stewart

Sun 8/16

10:28 am-10:57 pm

1 stop12h 29m

$357

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 11/12

9:42 pm-4:40 pm

1 stop18h 58m

New Windsor Stewart

Sun 11/15

12:00 pm-10:21 pm

1 stop10h 21m

$378

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 9/17

9:42 pm-11:36 am

2 stops13h 54m

New Windsor Stewart

Sun 9/20

10:56 am-6:28 pm

1 stop7h 32m

$406

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 8/8

4:05 pm-9:38 am

1 stop17h 33m

New Windsor Stewart

Wed 8/12

12:05 pm-5:22 pm

1 stop5h 17m

$416

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Fri 12/18

4:00 pm-11:39 am

1 stop19h 39m

New Windsor Stewart

Wed 12/23

12:39 pm-8:28 pm

1 stop7h 49m

$502
Cheapest one-way

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 10/17

8:10 am-11:03 am

1 stop26h 53m

$141

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 18 resultsSorted by cheapest first
1
2

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 July.
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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