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Stewart

$107+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Aug 26 — Sep 21
Tue 8/26
Tue 9/2
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 August 21, 2025.

Round-trip from

$200
(Mytrip)

One-way from

$107
(Mytrip)

Popular in

July

Cheapest in

September

Average price

$216
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 ($40 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 August 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 August 21, 2025.

This Mytrip deal was found by Cheapflights users on 8/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/138:27 pmTPA - SWF
1 stop13h 44mMultiple Airlines
Mon 11/1712:01 pmSWF - TPA
1 stop10h 17mMultiple Airlines
Deal found 8/19$200
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/910:59 pmTPA - SWF
1 stop11h 52mMultiple Airlines
Mon 10/1311:01 amSWF - TPA
1 stop12h 51mMultiple Airlines
Deal found 8/21$213
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/1610:59 pmTPA - SWF
1 stop11h 42mMultiple Airlines
Thu 10/235:45 pmSWF - TPA
2 stops13h 23mMultiple Airlines
Deal found 8/21$362
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/238:27 pmTPA - SWF
1 stop13h 40mMultiple Airlines
Wed 11/2612:17 pmSWF - TPA
1 stop19h 57mMultiple Airlines
Deal found 8/20$368
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/289:50 pmTPA - SWF
1 stop15h 15mMultiple Airlines
Mon 9/11:55 pmSWF - TPA
1 stop9h 02mMultiple Airlines
Deal found 8/20$369
This Mytrip deal was found by Cheapflights users on 8/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/296:00 amTPA - SWF
1 stop7h 05mMultiple Airlines
Mon 9/11:55 pmSWF - TPA
1 stop9h 02mMultiple Airlines
Deal found 8/21$370
This Booking.com deal was found by Cheapflights users on 8/21. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:00 pmTPA - SWF
1 stop22h 44mBreeze Airways
Mon 11/312:24 pmSWF - TPA
1 stop10h 28mBreeze Airways
Deal found 8/21$463
This Gotogate deal was found by Cheapflights users on 8/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/41:06 pmTPA - SWF
1 stop22h 38mBreeze Airways
Mon 9/812:24 pmSWF - TPA
1 stop10h 28mBreeze Airways
Deal found 8/19$472

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 August 21, 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

Thu 11/13

8:27 pm-10:11 am

1 stop13h 44m

New Windsor Stewart

Mon 11/17

12:01 pm-10:18 pm

1 stop10h 17m

$200

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 10/9

10:59 pm-10:51 am

1 stop11h 52m

New Windsor Stewart

Mon 10/13

11:01 am-11:52 pm

1 stop12h 51m

$213

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 10/16

10:59 pm-10:41 am

1 stop11h 42m

New Windsor Stewart

Thu 10/23

5:45 pm-7:08 am

2 stops13h 23m

$362

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 8/28

9:50 pm-1:05 pm

1 stop15h 15m

New Windsor Stewart

Mon 9/1

1:55 pm-10:57 pm

1 stop9h 02m

$369

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 10/5

4:29 pm-10:11 am

1 stop17h 42m

New Windsor Stewart

Sun 10/12

5:45 pm-7:08 am

2 stops13h 23m

$369

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 8/29

6:00 am-1:05 pm

1 stop7h 05m

New Windsor Stewart

Mon 9/1

1:55 pm-10:57 pm

1 stop9h 02m

$370

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 10/30

1:00 pm-11:44 am

1 stop22h 44m

New Windsor Stewart

Mon 11/3

12:24 pm-10:52 pm

1 stop10h 28m

$463

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 9/4

1:06 pm-11:44 am

1 stop22h 38m

New Windsor Stewart

Mon 9/8

12:24 pm-10:52 pm

1 stop10h 28m

$472

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 11/16

8:27 pm-11:11 am

1 stop14h 44m

$107

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 10/16

10:59 pm-10:41 am

1 stop11h 42m

$107

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 15 results
1
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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 August 21, 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 August 21, 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
2,916 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Crew

8.0

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
2,916 reviews
JetBlue
7.2
Good
2,916 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Crew

8.0

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
702 reviews
JetBlue
7.2
Good
2,916 reviews

Food

6.7

Boarding

7.4

Comfort

7.6

Entertainment

7.3

Crew

8.0

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 $79. While the most popular route (Tampa - New Windsor Stewart) can be booked for $200 on average our data indicates $148 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 August 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$58Average$197FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$160FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$119Average$204FlexibilityNo cancel feeOn-timeN/A

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