$82+ Cheap flights from Cleveland to New Windsor (CLE - SWF)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SWF
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Stewart with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Cleveland to Stewart
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Cheapest flights from Cleveland to StewartExplore 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 October 25, 2026.
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 October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/215:24 pm -
1 stop16h 21m
Thu 1/2812:25 pm -
1 stop11h 42m
Deal found 10/22![Multiple Airlines logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Fri 12/46:05 am -
2 stops29h 34m
Sun 12/136:49 pm -
1 stop29h 52m
Deal found 10/23![Multiple Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/215:24 pm -
1 stop16h 21m
Sat 1/3012:39 pm -
2 stops46h 12m
Deal found 10/22![Multiple Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/131:41 pm -
1 stop21h 58m
Mon 11/167:04 pm -
1 stop28h 02m
Deal found 10/22![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 11/118:18 pm -
1 stop13h 52m
Fri 11/135:30 pm -
1 stop15h 36m
Deal found 10/20![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/169:10 am -
1 stop26h 07m
Sun 1/108:01 pm -
1 stop18h 36m
Deal found 10/21![Multiple Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/39:10 am -
1 stop8h 49m
Sun 12/66:49 pm -
1 stop29h 52m
Deal found 10/25![Multiple Airlines logo]()
$253
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/215:24 pm -
1 stop16h 21m
Fri 1/2911:58 am -
2 stops12h 09m
Deal found 10/22![Multiple Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 12/65:18 pm -
1 stop16h 55m
Mon 12/1412:16 pm -
2 stops27h 47m
Deal found 10/20![Multiple Airlines logo]()
$273
Best flights from Cleveland to StewartDiscover carefully curated flight deals from Cleveland to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from Cleveland to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/131:41 pm -
1 stop21h 58m
Mon 11/167:04 pm -
1 stop28h 02m
Deal found 10/22![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 11/118:18 pm -
1 stop13h 52m
Fri 11/135:30 pm -
1 stop15h 36m
Deal found 10/20![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/24. 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.
Thu 12/39:10 am -
1 stop8h 49m
Sun 12/66:49 pm -
1 stop29h 52m
Deal found 10/24![Multiple Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 11/118:18 pm -
1 stop13h 52m
Sun 11/155:37 pm -
2 stops26h 43m
Deal found 10/20![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/199:59 pm -
1 stop12h 40m
Sun 11/226:48 pm -
1 stop29h 37m
Deal found 10/20![Multiple Airlines logo]()
$313
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/189:59 pm -
1 stop12h 17m
Sun 11/226:48 pm -
1 stop29h 37m
Deal found 10/22![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/235:33 pm -
1 stop16h 36m
Sat 12/512:39 pm -
2 stops11h 58m
Deal found 10/21![Multiple Airlines logo]()
$335
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/109:10 am -
1 stop8h 49m
Sun 12/136:49 pm -
1 stop29h 52m
Deal found 10/22![Multiple Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 10/23. 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.
Sat 11/77:18 am -
1 stop27h 52m
Wed 11/1112:39 pm -
2 stops20h 27m
Deal found 10/23![Multiple Airlines logo]()
$368
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/39:10 am -
1 stop8h 49m
Mon 12/712:16 pm -
2 stops12h 25m
Deal found 10/22![Multiple Airlines logo]()
$410
Last-minute flights from Cleveland to StewartDiscover last-minute flight deals from Cleveland to Stewart. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Stewart. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 10/289:18 pm -
1 stop12h 30m
Wed 11/412:39 pm -
2 stops20h 27m
Deal found 10/20![Multiple Airlines logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 10/289:18 pm -
1 stop12h 30m
Mon 11/27:01 pm -
1 stop14h 05m
Deal found 10/20![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 10/289:18 pm -
1 stop12h 30m
Fri 10/305:39 pm -
1 stop15h 27m
Deal found 10/20![Multiple Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sat 10/317:28 am -
1 stop28h 40m
Wed 11/412:39 pm -
2 stops20h 27m
Deal found 10/20![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sat 10/317:28 am -
1 stop28h 40m
Mon 11/27:01 pm -
1 stop14h 05m
Deal found 10/20![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Mon 11/26:00 am -
1 stop12h 11m
Wed 11/412:39 pm -
2 stops20h 27m
Deal found 10/20![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 11/118:18 pm -
1 stop13h 52m
Fri 11/135:30 pm -
1 stop15h 36m
Deal found 10/20![Multiple Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 11/118:18 pm -
1 stop13h 52m
Sun 11/155:37 pm -
2 stops26h 43m
Deal found 10/20![Multiple Airlines logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 11/131:41 pm -
1 stop21h 58m
Mon 11/167:04 pm -
1 stop28h 02m
Deal found 10/22![Multiple Airlines logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/174:11 pm -
2 stops19h 28m
Sun 11/226:48 pm -
1 stop29h 37m
Deal found 10/21![Multiple Airlines logo]()
$310
One-way flights from Cleveland to StewartSearch for one-way flight options from Cleveland to Stewart. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Cleveland to Stewart. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 1/77:25 am -
1 stop11h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$82
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/317:28 am -
1 stop28h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 10/289:18 pm -
1 stop12h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/145:41 pm -
2 stops41h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 10/22. 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 12/65:18 pm -
1 stop16h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/39:59 pm -
2 stops13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$129
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 October 25, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $206 (Kiwi.com) |
One-way from | $82 (Kiwi.com) |
Popular in | September |
Cheapest in | May |
Average price | $299 |
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 7,457,451 searches. Data last updated October 25, 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
Cheapest round-trip
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Wed 10/28
9:18 pm-9:48 am
1 stop12h 30m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$119
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Mon 12/14
5:41 pm-11:39 am
2 stops41h 58m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$127
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Tue 11/3
9:59 pm-11:39 am
2 stops13h 40m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$129
Quickest round-trip
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Wed 11/11
9:59 pm-10:16 am
1 stop12h 17m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$135
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Wed 12/9
5:18 pm-10:26 am
1 stop17h 08m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$164
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Thu 11/19
8:31 pm-11:39 am
2 stops39h 08m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$175
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Fri 11/20
5:30 am-11:39 am
2 stops30h 09m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$191
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Thu 11/12
9:59 pm-11:36 am
2 stops13h 37m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$201
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Fri 12/18
6:10 pm-11:39 am
2 stops17h 29m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$224
ClevelandNew Windsor
CLE Cleveland Hopkins Intl - SWF New Windsor Stewart
CLESWF
Cleveland Hopkins Intl
Fri 10/30
9:18 pm-11:16 am
3 stops37h 58m
New Windsor Stewart
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$227
Showing 1-10 of 20 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
CLE-SWF
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.
Traveling to a place near New Windsor?
Book flights to New Windsor if you plan to visit one of these locationsKingston
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