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Stewart

$115+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
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 March 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/10. 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 5/1710:00 pm
CLE
-
SWF
1 stop12h 55m
Multiple Airlines
Thu 5/2110:28 am
SWF
-
CLE
1 stop12h 12m
Multiple Airlines
Deal found 3/10$259
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 3/184:40 pm
CLE
-
SWF
1 stop16h 59m
Multiple Airlines
Sun 3/2210:29 am
SWF
-
CLE
1 stop15h 23m
Multiple Airlines
Deal found 3/7$280
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/298:30 am
CLE
-
SWF
1 stop26h 55m
Multiple Airlines
Mon 6/19:41 am
SWF
-
CLE
1 stop10h 45m
Multiple Airlines
Deal found 3/9$284
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/228:30 am
CLE
-
SWF
1 stop26h 55m
Multiple Airlines
Mon 5/259:41 am
SWF
-
CLE
1 stop14h 58m
Multiple Airlines
Deal found 3/9$293
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/810:00 pm
CLE
-
SWF
2 stops13h 25m
Multiple Airlines
Sun 5/1011:45 am
SWF
-
CLE
1 stop10h 17m
Multiple Airlines
Deal found 3/8$296
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/319:57 pm
CLE
-
SWF
1 stop10h 54m
Multiple Airlines
Sun 6/710:28 am
SWF
-
CLE
1 stop12h 12m
Multiple Airlines
Deal found 3/11$324
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:45 am
CLE
-
SWF
1 stop25h 53m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
CLE
1 stop4h 55m
Multiple Airlines
Deal found 3/11$329
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/268:30 am
CLE
-
SWF
1 stop26h 55m
Multiple Airlines
Wed 7/112:05 pm
SWF
-
CLE
2 stops20h 35m
Multiple Airlines
Deal found 3/11$335
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/232:59 pm
CLE
-
SWF
1 stop18h 39m
Multiple Airlines
Mon 5/259:41 am
SWF
-
CLE
1 stop14h 58m
Multiple Airlines
Deal found 3/9$345
This Kiwi.com deal was found by Cheapflights users on 3/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/309:57 pm
CLE
-
SWF
1 stop11h 01m
Multiple Airlines
Sat 6/612:05 pm
SWF
-
CLE
1 stop4h 55m
Multiple Airlines
Deal found 3/11$355

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 March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Kiwi.com)

One-way from

$115
(Kiwi.com)

Popular in

December

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. 16% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 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 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 March 12, 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

Sun 5/17

10:00 pm-10:55 am

1 stop12h 55m

New Windsor Stewart

Thu 5/21

10:28 am-10:40 pm

1 stop12h 12m

$259

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 3/18

4:40 pm-9:39 am

1 stop16h 59m

New Windsor Stewart

Sun 3/22

10:29 am-1:52 am

1 stop15h 23m

$280

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Fri 5/22

8:30 am-11:25 am

1 stop26h 55m

New Windsor Stewart

Mon 5/25

9:41 am-12:39 am

1 stop14h 58m

$293

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Fri 5/8

10:00 pm-11:25 am

2 stops13h 25m

New Windsor Stewart

Sun 5/10

11:45 am-10:02 pm

1 stop10h 17m

$297
Quickest round-trip

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 5/31

9:57 pm-8:51 am

1 stop10h 54m

New Windsor Stewart

Sun 6/7

10:28 am-10:40 pm

1 stop12h 12m

$324

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 6/3

7:45 am-9:38 am

1 stop25h 53m

New Windsor Stewart

Sat 6/6

12:05 pm-5:00 pm

1 stop4h 55m

$329

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sat 5/23

2:59 pm-9:38 am

1 stop18h 39m

New Windsor Stewart

Mon 5/25

9:41 am-12:39 am

1 stop14h 58m

$345

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Sun 3/15

10:00 pm-9:02 am

1 stop11h 02m

New Windsor Stewart

Sun 3/22

10:29 am-1:52 am

1 stop15h 23m

$430

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Thu 3/26

10:00 pm-8:57 am

1 stop10h 57m

New Windsor Stewart

Mon 3/30

9:47 am-7:42 am

1 stop21h 55m

$433

ClevelandNew Windsor

CLE - SWF

CLESWF

Cleveland Hopkins Intl

Wed 5/6

8:01 pm-8:58 am

1 stop12h 57m

New Windsor Stewart

Mon 5/11

12:15 pm-1:10 am

2 stops12h 55m

$568

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 17 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 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 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.

Cheapflights Insights

Everything you need to know about your flight from Cleveland to New Windsor

What is the cheapest month to book a flight from Cleveland to New Windsor?

Currently, May is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $49). Flying from Cleveland to New Windsor in June is currently the most expensive (average of $80). 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 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.

  • What is the cheapest month to book a flight from Cleveland to New Windsor?

    Currently, May is the cheapest month in which you can book a flight from Cleveland to New Windsor (average of $49). Flying from Cleveland to New Windsor in June is currently the most expensive (average of $80). 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 New Windsor?

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

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