$78+ Cheap flights from New Windsor (SWF) to Clearwater, FL
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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Sep 28 — Oct 51
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to Clearwater 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
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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 Stewart to Clearwater
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Cheapest flights from Stewart to ClearwaterExplore the most affordable flight options available from Stewart to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
Explore the most affordable flight options available from Stewart to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Sat 10/312:39 pm -
1 stop4h 38m
Sat 10/177:00 am -
1 stop4h 39m
Deal found 8/25![Breeze Airways logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 10/312:39 pm -
1 stop4h 38m
Wed 10/77:00 am -
1 stop4h 39m
Deal found 8/26![Breeze Airways logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Sat 10/312:39 pm -
1 stop4h 38m
Wed 10/147:00 am -
1 stop4h 39m
Deal found 8/25![Breeze Airways logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Sat 9/2612:39 pm -
1 stop4h 38m
Sat 10/37:00 am -
1 stop4h 39m
Deal found 8/25![Breeze Airways logo]()
$167
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:39 pm -
1 stop4h 38m
Wed 9/307:00 am -
1 stop4h 39m
Deal found 8/28![Breeze Airways logo]()
$173
Best flights from Stewart to ClearwaterDiscover carefully curated flight deals from Stewart to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
Discover carefully curated flight deals from Stewart to Clearwater that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 29, 2026.
This Breeze Airways deal was found by Cheapflights users on 8/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:39 pm -
1 stop4h 38m
Sat 10/37:00 am -
1 stop4h 39m
Deal found 8/27![Breeze Airways logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/2511:58 am -
1 stop19h 07m
Fri 10/3010:06 am -
1 stop7h 59m
Deal found 8/28![Multiple Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sat 9/1212:39 pm -
1 stop4h 38m
Sat 9/197:00 am -
1 stop4h 39m
Deal found 8/27![Breeze Airways logo]()
$188
This CheapOair deal was found by Cheapflights users on 8/25. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:39 pm -
1 stop4h 38m
Sat 9/267:00 am -
1 stop4h 39m
Deal found 8/25![Breeze Airways logo]()
$195
This Breeze Airways deal was found by Cheapflights users on 8/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/712:39 pm -
1 stop4h 38m
Wed 10/147:00 am -
1 stop4h 39m
Deal found 8/29![Breeze Airways logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/512:05 pm -
1 stop4h 21m
Fri 9/112:00 pm -
1 stop21h 39m
Deal found 8/26![Multiple Airlines logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 8/26. 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.
Sat 9/512:05 pm -
1 stop4h 21m
Sat 9/127:00 am -
1 stop4h 39m
Deal found 8/26![Breeze Airways logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Fri 9/412:11 pm -
1 stop10h 07m
Fri 9/111:21 pm -
1 stop22h 18m
Deal found 8/25![Multiple Airlines logo]()
$362
This Kiwi.com deal was found by Cheapflights users on 8/27. 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 9/1412:16 pm -
1 stop10h 12m
Thu 9/1710:53 pm -
2 stops13h 28m
Deal found 8/27![Multiple Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/1012:39 pm -
1 stop11h 05m
Mon 10/1210:06 am -
1 stop6h 50m
Deal found 8/28![Multiple Airlines logo]()
$421
This Kiwi.com deal was found by Cheapflights users on 8/25. 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 9/2410:56 am -
2 stops11h 38m
Sun 9/2710:36 am -
1 stop6h 55m
Deal found 8/25![Multiple Airlines logo]()
$425
Last-minute flights from Stewart to ClearwaterDiscover last-minute flight deals from Stewart to Clearwater. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Clearwater. Data last updated August 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 9/1612:39 pm -
1 stop4h 38m
Sat 9/197:00 am -
1 stop4h 39m
Deal found 8/26![Breeze Airways logo]()
$180
This CheapOair deal was found by Cheapflights users on 8/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:39 pm -
1 stop4h 38m
Sat 9/267:00 am -
1 stop4h 39m
Deal found 8/27![Breeze Airways logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sat 9/1912:39 pm -
1 stop4h 38m
Wed 9/307:00 am -
1 stop4h 39m
Deal found 8/27![Breeze Airways logo]()
$179
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2312:39 pm -
1 stop4h 38m
Wed 9/307:00 am -
1 stop4h 39m
Deal found 8/28![Breeze Airways logo]()
$173
This Breeze Airways deal was found by Cheapflights users on 8/27. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/2612:39 pm -
1 stop4h 38m
Sat 10/37:00 am -
1 stop4h 39m
Deal found 8/27![Breeze Airways logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Sat 9/2612:39 pm -
1 stop4h 38m
Wed 10/77:00 am -
1 stop4h 39m
Deal found 8/25![Breeze Airways logo]()
$183
One-way flights from Stewart to ClearwaterSearch for one-way flight options from Stewart to Clearwater. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
Search for one-way flight options from Stewart to Clearwater. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 10/312:39 pm -
1 stop4h 38m
Deal found 8/28![Breeze Airways logo]()
$78
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 9/1912:39 pm -
1 stop4h 38m
Deal found 8/28![Breeze Airways logo]()
$84
This Kiwi.com deal was found by Cheapflights users on 8/25. 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.
Wed 9/1612:39 pm -
1 stop4h 38m
Deal found 8/25![Breeze Airways logo]()
$85
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 11/226:48 pm -
1 stop12h 17m
Deal found 8/26![Multiple Airlines logo]()
$90
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sat 9/2612:39 pm -
1 stop11h 05m
Deal found 8/27![Breeze Airways logo]()
$96
This Kiwi.com deal was found by Cheapflights users on 8/27. 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.
Sun 11/1512:00 pm -
1 stop19h 05m
Deal found 8/27![Multiple Airlines logo]()
$98
Find flight deals from Stewart to Clearwater
Keep the following information in mind while searching for Stewart to Clearwater flight deals. Data was last updated August 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $149 (Kiwi.com) |
One-way from | $78 (Kiwi.com) |
Popular in | March |
Cheapest in | September |
Average price | $243 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to Clearwater 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 August 29, 2026.
Use the filters below to find and compare flights from New Windsor to Clearwater that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 9/26
12:39 pm-5:17 pm
1 stop4h 38m
Tampa
Sat 10/3
7:00 am-11:39 am
1 stop4h 39m
$163
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 9/12
12:39 pm-5:17 pm
1 stop4h 38m
Tampa
Sat 9/19
7:00 am-11:39 am
1 stop4h 39m
$188
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 9/19
12:39 pm-5:17 pm
1 stop4h 38m
Tampa
Sat 9/26
7:00 am-11:39 am
1 stop4h 39m
$195
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Wed 10/7
12:39 pm-5:17 pm
1 stop4h 38m
Tampa
Wed 10/14
7:00 am-11:39 am
1 stop4h 39m
$225
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sun 10/25
11:58 am-7:05 am
1 stop19h 07m
Tampa
Fri 10/30
10:06 am-6:05 pm
1 stop7h 59m
$236
Quickest round-trip
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 9/5
12:05 pm-4:26 pm
1 stop4h 21m
Tampa
Sat 9/12
7:00 am-11:39 am
1 stop4h 39m
$254
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 9/5
12:05 pm-4:26 pm
1 stop4h 21m
Tampa
Fri 9/11
2:00 pm-11:39 am
1 stop21h 39m
$281
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Fri 9/4
12:11 pm-10:18 pm
1 stop10h 07m
Tampa
Fri 9/11
1:21 pm-11:39 am
1 stop22h 18m
$362
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Mon 9/14
12:16 pm-10:28 pm
1 stop10h 12m
Tampa
Thu 9/17
10:53 pm-12:21 pm
2 stops13h 28m
$419
New WindsorTampa
SWF New Windsor Stewart - TPA Tampa
SWFTPA
New Windsor Stewart
Sat 10/10
12:39 pm-11:44 pm
1 stop11h 05m
Tampa
Mon 10/12
10:06 am-4:56 pm
1 stop6h 50m
$421
Showing 1-10 of 23 resultsSorted by cheapest first
Best time to book a flight from Stewart to Clearwater
Have a flexible travel schedule? Discover the best time to fly to Clearwater from Stewart with our price prediction graph.
SWF-TPA
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 Clearwater
SWF-CL9
SWF-TPA
What is the cheapest time of day to fly from SWF to CL9?
Find hourly flight availability from Stewart to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 29, 2026.
It’s optimal to fly from New Windsor to Clearwater in the afternoon. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight at noon.
How much does it cost to fly round-trip from New Windsor to Clearwater?
Airfare is typical for this route at the moment.
New Windsor to Clearwater flights typically cost between $121 and $206 in October.The cheapest round-trip price found within the last 5 days was $149 on Breeze Airways (Oct 3-Oct 17).
Reviews of airlines servicing Clearwater
Get insights into the airlines that provide service to Clearwater. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Clearwater. Reviews last updated August 29, 2026.
Get a feel of what it's like to fly with Breeze Airways,Allegiant Air, andJetBlue from New Windsor to Clearwater by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Comfort
8.2
Crew
8.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Comfort
8.2
Crew
8.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Comfort
8.2
Crew
8.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Boarding
8.3
Overall
8.2
Food
6.7
Entertainment
6.7
Comfort
8.2
Crew
8.8
Reviews
1 / 18
4.0
OkayLisa,Mar 2026
ORF - JAX
Related info for your journey
Find useful and relevant information for your journey from Stewart to Clearwater. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Stewart and Clearwater flights
Browse other Stewart and Clearwater flight options. Last updated on August 29, 2026.
Popular flight searches
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Consider these flights traveling from Stewart to Clearwater.
Top 4 airlines flying from Stewart to Clearwater
Discover the top 4 airlines that operate flights from Stewart to Clearwater. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$43 | Average$148 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$80 | Average$201 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$128 | Average$225 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$230 | FlexibilityNo cancel fee | On-time62% |