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Stewart

$93+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Nov 21 — Nov 281
Fri 11/21
Fri 11/28
1 adult, Economy
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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 October 22, 2025.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:11 pmTPA - SWF
1 stop15h 26mMultiple Airlines
Mon 12/1512:27 pmSWF - TPA
1 stop6h 28mMultiple Airlines
Deal found 10/20$180
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/68:08 pmTPA - SWF
1 stop14h 33mMultiple Airlines
Mon 11/1012:01 pmSWF - TPA
1 stop10h 50mMultiple Airlines
Deal found 10/22$193
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/276:28 amTPA - SWF
1 stop7h 43mMultiple Airlines
Fri 10/3111:31 amSWF - TPA
1 stop11h 55mMultiple Airlines
Deal found 10/21$231
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/259:03 pmTPA - SWF
1 stop14h 04mMultiple Airlines
Fri 1/911:09 amSWF - TPA
1 stop11h 09mMultiple Airlines
Deal found 10/20$250
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:11 pmTPA - SWF
1 stop15h 26mMultiple Airlines
Mon 1/1911:09 amSWF - TPA
1 stop11h 09mMultiple Airlines
Deal found 10/21$272
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.
Fri 12/58:11 pmTPA - SWF
2 stops38h 52mMultiple Airlines
Fri 12/1212:27 pmSWF - TPA
1 stop6h 28mMultiple Airlines
Deal found 10/21$277
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 10/307:15 amTPA - SWF
1 stop5h 30mMultiple Airlines
Fri 10/3111:31 amSWF - TPA
1 stop11h 55mMultiple Airlines
Deal found 10/21$288
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 11/208:01 pmTPA - SWF
1 stop14h 21mMultiple Airlines
Sun 11/308:41 pmSWF - TPA
2 stops15h 42mMultiple Airlines
Deal found 10/21$292
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/118:11 pmTPA - SWF
1 stop15h 26mMultiple Airlines
Mon 12/228:25 pmSWF - TPA
1 stop11h 11mMultiple Airlines
Deal found 10/20$309

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 October 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$180
(Mytrip)

One-way from

$93
(Mytrip)

Popular in

November

Cheapest in

September

Average price

$161
Provider with most accurate pricing for Tampa-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Tampa-New York (NYC) flights.
Search Deals
From Clearwater to New Windsor Stewart
Search Deals
One-way flight from Clearwater to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($27 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 22, 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 12/11

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Mon 12/15

12:27 pm-6:55 pm

1 stop6h 28m

$180

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 11/6

8:08 pm-10:41 am

1 stop14h 33m

New Windsor Stewart

Mon 11/10

12:01 pm-10:51 pm

1 stop10h 50m

$193

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 1/25

8:27 pm-10:19 am

1 stop13h 52m

New Windsor Stewart

Fri 1/30

11:09 am-10:18 pm

1 stop11h 09m

$193

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 12/25

9:03 pm-11:07 am

1 stop14h 04m

New Windsor Stewart

Fri 1/9

11:09 am-10:18 pm

1 stop11h 09m

$250

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 12/5

8:11 pm-11:03 am

2 stops38h 52m

New Windsor Stewart

Fri 12/12

12:27 pm-6:55 pm

1 stop6h 28m

$277

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 12/11

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Mon 12/22

8:25 pm-7:36 am

1 stop11h 11m

$309

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 11/12

12:14 pm-11:03 am

2 stops22h 49m

New Windsor Stewart

Sun 11/16

1:32 pm-3:56 pm

1 stop26h 24m

$310

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Mon 11/17

7:10 am-5:37 pm

1 stop10h 27m

New Windsor Stewart

Mon 11/24

10:57 am-8:37 pm

1 stop9h 40m

$322

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 11/20

8:01 pm-10:22 am

1 stop14h 21m

New Windsor Stewart

Sun 11/30

10:12 am-7:20 am

1 stop21h 08m

$349

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 12/14

8:11 pm-11:37 am

1 stop15h 26m

New Windsor Stewart

Fri 12/19

6:56 pm-7:36 am

1 stop12h 40m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

Showing 1-10 of 18 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, January is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $38). Flying from Clearwater to New Windsor in June is currently the most expensive (average of $64). 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 October 22, 2025.

One of the essential ways to save on airfare from Clearwater to New Windsor is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 36% on airfare.

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 October 22, 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
2,909 reviews

Boarding

7.4

Overall

7.2

Crew

8.0

Food

6.7

Comfort

7.6

Entertainment

7.3

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
2,909 reviews
JetBlue
7.2
Good
2,909 reviews

Boarding

7.4

Overall

7.2

Crew

8.0

Food

6.7

Comfort

7.6

Entertainment

7.3

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
694 reviews
JetBlue
7.2
Good
2,909 reviews

Boarding

7.4

Overall

7.2

Crew

8.0

Food

6.7

Comfort

7.6

Entertainment

7.3

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 $84. While the most popular route (Tampa - New Windsor Stewart) can be booked for $192 on average, our data indicates $273 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, January is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $38). Flying from Clearwater to New Windsor in June is currently the most expensive (average of $64). 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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Alternative routes for Clearwater to Stewart

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 October 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$74Average$160FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$198FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$187Average$212FlexibilityNo cancel feeOn-time62%

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