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Stewart

$78+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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 January 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$157
(CheapOair)

One-way from

$78
(Mytrip)

Popular in

July

Cheapest in

September

Average price

$119
Provider with most accurate pricing for Tampa-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Tampa-New York (NYC) flights.
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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. 14% potential increase in price ($32 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 8, 2026.

This CheapOair deal was found by Cheapflights users on 1/7. 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 5/67:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Sat 5/912:05 pmSWF - TPA
1 stop4h 16mBreeze Airways
Deal found 1/7$157
This Kiwi.com deal was found by Cheapflights users on 1/6. 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 8/267:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Sat 8/2912:05 pmSWF - TPA
1 stop4h 16mBreeze Airways
Deal found 1/6$170
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 9/97:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Mon 9/1412:15 pmSWF - TPA
1 stop10h 40mBreeze Airways
Deal found 1/7$175
This Mytrip deal was found by Cheapflights users on 1/7. 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 1/229:47 pmTPA - SWF
1 stop12h 32mMultiple Airlines
Mon 1/2611:09 amSWF - TPA
1 stop6h 24mMultiple Airlines
Deal found 1/7$183
This Kiwi.com deal was found by Cheapflights users on 1/8. 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 6/37:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Mon 6/812:15 pmSWF - TPA
1 stop10h 40mBreeze Airways
Deal found 1/8$196
This Breeze Airways deal was found by Cheapflights users on 1/7. 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 5/277:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Sat 5/3012:05 pmSWF - TPA
1 stop4h 16mBreeze Airways
Deal found 1/7$199
This Priceline deal was found by Cheapflights users on 1/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/107:00 amTPA - SWF
1 stop4h 25mBreeze Airways
Sat 6/1312:05 pmSWF - TPA
1 stop4h 16mBreeze Airways
Deal found 1/7$209
This Kiwi.com deal was found by Cheapflights users on 1/7. 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 1/159:47 pmTPA - SWF
1 stop12h 32mMultiple Airlines
Mon 1/1912:11 pmSWF - TPA
1 stop9h 46mMultiple Airlines
Deal found 1/7$221

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 January 8, 2026.
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

Wed 5/6

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Sat 5/9

12:05 pm-4:21 pm

1 stop4h 16m

$157

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 1/22

9:47 pm-10:19 am

1 stop12h 32m

New Windsor Stewart

Mon 1/26

11:09 am-5:33 pm

1 stop6h 24m

$184

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 6/3

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Mon 6/8

12:15 pm-10:55 pm

1 stop10h 40m

$196

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 5/27

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Sat 5/30

12:05 pm-4:21 pm

1 stop4h 16m

$199

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 2/5

8:38 am-10:19 am

1 stop25h 41m

New Windsor Stewart

Thu 2/12

11:42 am-9:00 pm

1 stop9h 18m

$263

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 2/1

9:47 pm-10:19 am

1 stop12h 32m

New Windsor Stewart

Thu 2/5

6:49 pm-8:00 pm

1 stop25h 11m

$272

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sat 5/30

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Wed 6/3

12:05 pm-4:21 pm

1 stop4h 16m

$273

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 5/7

10:38 am-5:25 pm

1 stop6h 47m

New Windsor Stewart

Sat 5/9

12:05 pm-4:21 pm

1 stop4h 16m

$278

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sat 5/30

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Sat 6/6

12:05 pm-4:21 pm

1 stop4h 16m

$280

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 2/11

9:47 pm-10:52 am

1 stop13h 05m

$78

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 20 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, March is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $41). Flying from Clearwater to New Windsor in April 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 January 8, 2026.

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 January 8, 2026.
Read reviews from past customers who have flown JetBlue 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
2,893 reviews

Boarding

7.4

Entertainment

7.2

Food

6.6

Comfort

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Samuel,Nov 2025

PBI - HPN

Incessant announcements hawking the JB Card, other items to purchase, seat back tables up 45 minutes before we landed....more announcements....Give your customer a break!
JetBlue
7.2
Good
2,893 reviews
JetBlue
7.2
Good
2,893 reviews

Boarding

7.4

Entertainment

7.2

Food

6.6

Comfort

7.5

Crew

8.0

Overall

7.2

Reviews

1 / 20
2.0
Mediocre

Samuel,Nov 2025

PBI - HPN

Incessant announcements hawking the JB Card, other items to purchase, seat back tables up 45 minutes before we landed....more announcements....Give your customer a break!

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.

  • How long is the flight from Clearwater to New Windsor?

    There are many flights that can get you from Clearwater to New Windsor in 4h 25m. Fly via Breeze Airways to get the fastest option. Clearwater and New Windsor are separated by a distance of 1048 mi.

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

    Looking at all options, your cheapest flight can be booked for $76. While the most popular route (Tampa - New Windsor Stewart) can be booked for $157 on average, our data indicates $162 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, March is the cheapest month in which you can book a flight from Clearwater to New Windsor (average of $41). Flying from Clearwater to New Windsor in April 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$76Average$163FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$116Average$195FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$208FlexibilityNo cancel feeOn-time62%

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