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Stewart

$91+ Cheap flights from Clearwater, FL to New Windsor (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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
out 16 — out 231
qui 10/16
qui 10/23
1 adult, Economy
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Cheap flight deals from Clearwater to Stewart

Keep the following information in mind while searching for Clearwater to Stewart flight deals. Data was last updated setembro 16, 2025.

Round-trip from

$266
(Kiwi.com)

One-way from

$91
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$93
From Clearwater to New Windsor Stewart
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One-way flight from Clearwater to New Windsor Stewart
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Highest demand for flights based on searches. 17% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Clearwater to Stewart

Cheapest flights from Clearwater to Stewart
Explore the most affordable flight options available from Clearwater to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on setembro 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
qui 11/208:27 pmTPA - SWF
1 stop13h 55mMultiple Airlines
seg 11/2410:57 amSWF - TPA
1 stop11h 21mMultiple Airlines
Deal found 9/14$266
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom 11/168:27 pmTPA - SWF
1 stop14h 44mMultiple Airlines
seg 11/2410:57 amSWF - TPA
1 stop11h 21mMultiple Airlines
Deal found 9/14$267
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom 11/168:27 pmTPA - SWF
1 stop14h 44mMultiple Airlines
sex 11/2111:12 amSWF - TPA
1 stop21h 02mMultiple Airlines
Deal found 9/14$271
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
dom 10/57:15 amTPA - SWF
1 stop9h 40mMultiple Airlines
seg 10/611:01 amSWF - TPA
1 stop6h 18mMultiple Airlines
Deal found 9/16$291
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom 11/168:27 pmTPA - SWF
1 stop14h 44mMultiple Airlines
qui 11/2011:43 amSWF - TPA
2 stops23h 21mMultiple Airlines
Deal found 9/14$301
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom 10/511:02 pmTPA - SWF
1 stop11h 09mMultiple Airlines
qui 10/911:43 amSWF - TPA
2 stops27h 29mMultiple Airlines
Deal found 9/14$307
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
qui 11/208:27 pmTPA - SWF
1 stop13h 55mMultiple Airlines
dom 11/236:23 pmSWF - TPA
1 stop21h 33mMultiple Airlines
Deal found 9/14$323
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
dom 11/168:27 pmTPA - SWF
1 stop14h 44mMultiple Airlines
dom 11/236:23 pmSWF - TPA
1 stop21h 33mMultiple Airlines
Deal found 9/14$324
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sex 11/147:10 amTPA - SWF
1 stop9h 50mMultiple Airlines
seg 11/2410:57 amSWF - TPA
1 stop11h 21mMultiple Airlines
Deal found 9/14$335
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
sex 11/147:10 amTPA - SWF
1 stop9h 50mMultiple Airlines
sex 11/2111:12 amSWF - TPA
1 stop21h 02mMultiple Airlines
Deal found 9/14$339

Cheapflights Fare Finder

 
Customize your flight search to find flights from Clearwater 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 setembro 16, 2025.
Use the filters below to find and compare flights from Clearwater to New Windsor that are best for you.

Fly from

Clearwater

Fly to

Stewart

Route

Depart

Return

Price

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

qui 11/20

8:27 pm-10:22 am

1 stop13h 55m

New Windsor Stewart

seg 11/24

10:57 am-10:18 pm

1 stop11h 21m

$266

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

dom 11/16

8:27 pm-11:11 am

1 stop14h 44m

New Windsor Stewart

seg 11/24

10:57 am-10:18 pm

1 stop11h 21m

$267

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

qui 11/20

8:27 pm-10:22 am

1 stop13h 55m

New Windsor Stewart

dom 11/23

6:23 pm-3:56 pm

1 stop21h 33m

$323

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

seg 11/17

7:10 am-5:37 pm

1 stop10h 27m

New Windsor Stewart

seg 11/24

10:57 am-10:18 pm

1 stop11h 21m

$342

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

seg 11/17

7:10 am-5:37 pm

1 stop10h 27m

New Windsor Stewart

sex 11/21

11:12 am-8:14 am

1 stop21h 02m

$346

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

sáb 11/15

3:30 pm-11:03 am

2 stops19h 33m

New Windsor Stewart

seg 11/24

10:57 am-10:18 pm

1 stop11h 21m

$356

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

dom 10/19

11:02 pm-10:11 am

1 stop11h 09m

New Windsor Stewart

qui 10/23

5:45 pm-3:56 pm

1 stop22h 11m

$357

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

sex 11/14

7:10 am-5:00 pm

1 stop9h 50m

New Windsor Stewart

qui 11/20

6:23 pm-3:56 pm

1 stop21h 33m

$403

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

seg 11/17

7:10 am-5:37 pm

1 stop10h 27m

New Windsor Stewart

qui 11/20

6:23 pm-3:56 pm

1 stop21h 33m

$409

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

qui 10/30

7:15 am-12:45 pm

1 stop5h 30m

New Windsor Stewart

sex 10/31

12:24 pm-10:52 pm

1 stop10h 28m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 19 results
1
2

Best time to book a flight from Clearwater to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Clearwater 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 Clearwater to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $109). Flying from Clearwater to New Windsor in December is currently the most expensive (average of $202). 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.

What is the cheapest time of day to fly from CL9 to SWF?

Find hourly flight availability from Clearwater to Stewart. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated setembro 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Clearwater to New Windsor as you normally would.

Reviews of airlines servicing Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated setembro 16, 2025.
Read reviews from past customers who have flown JetBlue and Allegiant Air from Clearwater to New Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,914 reviews

Entertainment

7.2

Crew

8.0

Boarding

7.4

Food

6.7

Comfort

7.6

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
JetBlue
7.2
Good
2,914 reviews
JetBlue
7.2
Good
2,914 reviews

Entertainment

7.2

Crew

8.0

Boarding

7.4

Food

6.7

Comfort

7.6

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.
Allegiant Air
7.2
Good
699 reviews
JetBlue
7.2
Good
2,914 reviews

Entertainment

7.2

Crew

8.0

Boarding

7.4

Food

6.7

Comfort

7.6

Overall

7.2

Reviews

1 / 20
10.0
Excellent

Geri,May 2025

RSW - BOS

Full flight, even thought I had priority A boarding, the flight was more than 1/2 full with Mint & Mosaic members, before I could board and get overhead space.

Related info for your journey

Find useful and relevant information for your journey from Clearwater to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to New Windsor from Clearwater?

    If you book a flight to New Windsor from Clearwater, you will be flying to Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor. There are 0 flights from Clearwater to Stewart per day from 3 different airlines.

  • What are the cheapest flights from Clearwater to New Windsor?

    Looking at all options, your cheapest flight can be booked for $59. While the most popular route (Tampa - New Windsor Stewart) can be booked for $322 on average, our data indicates $153 when flying from Clearwater to New Windsor.

  • Can I find deals for flights from Clearwater to Stewart that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Clearwater 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 Clearwater to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $109). Flying from Clearwater to New Windsor in December is currently the most expensive (average of $202). 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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See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Clearwater to Stewart

Discover the top 3 airlines that operate flights from Clearwater to Stewart. 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 2,558,603 searches. Data last updated setembro 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$159FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$199FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$126Average$197FlexibilityNo cancel feeOn-time62%

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