HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$54+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Clearwater to Stewart 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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

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 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 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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 5/307:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Wed 6/312:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/28$152
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 6/177:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Wed 6/2412:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/27$177
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/197:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Mon 8/2412:15 pm
SWF
-
TPA
1 stop10h 40m
Breeze Airways
Deal found 1/27$178
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 6/177:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Sat 6/2012:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/27$187
This CheapOair deal was found by Cheapflights users on 1/28. 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 5/67:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Fri 7/1012:15 pm
SWF
-
TPA
1 stop10h 40m
Breeze Airways
Deal found 1/28$192
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 5/291:25 pm
TPA
-
SWF
1 stop22h 00m
Breeze Airways
Wed 6/312:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/28$200
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 6/207:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Wed 6/2412:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/27$202
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 6/247:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Wed 7/812:05 pm
SWF
-
TPA
1 stop4h 16m
Breeze Airways
Deal found 1/27$211
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 2/59:47 pm
TPA
-
SWF
1 stop12h 32m
Multiple Airlines
Mon 2/911:09 am
SWF
-
TPA
1 stop21h 11m
Multiple Airlines
Deal found 1/28$214
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 7/87:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Mon 7/1312:15 pm
SWF
-
TPA
1 stop10h 40m
Breeze Airways
Deal found 1/27$218
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 6/177:00 am
TPA
-
SWF
1 stop4h 25m
Breeze Airways
Mon 6/2212:15 pm
SWF
-
TPA
1 stop10h 40m
Breeze Airways
Deal found 1/27$232
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Thu 9/312:26 pm
TPA
-
SWF
1 stop23h 09m
Breeze Airways
Mon 9/712:15 pm
SWF
-
TPA
1 stop10h 40m
Breeze Airways
Deal found 1/28$236

Find 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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$152
(Kiwi.com)

One-way from

$54
(CheapOair)

Popular in

July

Cheapest in

September

Average price

$119
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 ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 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

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

$152

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 6/17

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Wed 6/24

12:05 pm-4:21 pm

1 stop4h 16m

$177

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 6/17

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Sat 6/20

12:05 pm-4:21 pm

1 stop4h 16m

$187

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 5/6

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Fri 7/10

12:15 pm-10:55 pm

1 stop10h 40m

$192

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 5/29

1:25 pm-11:25 am

1 stop22h 00m

New Windsor Stewart

Wed 6/3

12:05 pm-4:21 pm

1 stop4h 16m

$200

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sat 6/20

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Wed 6/24

12:05 pm-4:21 pm

1 stop4h 16m

$202

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Wed 7/8

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Mon 7/13

12:15 pm-10:55 pm

1 stop10h 40m

$218

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sat 6/20

7:00 am-11:25 am

1 stop4h 25m

New Windsor Stewart

Mon 6/22

12:15 pm-10:55 pm

1 stop10h 40m

$257

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 7/17

1:25 pm-11:25 am

1 stop22h 00m

New Windsor Stewart

Sat 7/25

12:05 pm-4:21 pm

1 stop4h 16m

$286

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 5/8

8:00 am-11:25 am

1 stop27h 25m

New Windsor Stewart

Sun 5/10

11:45 am-9:59 pm

1 stop10h 14m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 21 results
1
2
3

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 $65). 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 29, 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 29, 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
2,891 reviews

Comfort

7.5

Entertainment

7.2

Food

6.6

Boarding

7.4

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
2,891 reviews
JetBlue
7.2
Good
2,891 reviews

Comfort

7.5

Entertainment

7.2

Food

6.6

Boarding

7.4

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 $59. While the most popular route (Tampa - New Windsor Stewart) can be booked for $152 on average, our data indicates $171 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 $65). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Clearwater to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Fort Lauderdale to John F Kennedy Intl flights
Miami to John F Kennedy Intl flights
Fort Lauderdale to Newark flights
Fort Lauderdale to LaGuardia flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Miami to Newark flights
Tampa to John F Kennedy Intl flights
West Palm Beach to Newark flights
Tampa to LaGuardia flights
Orlando to Newark flights
Orlando to LaGuardia flights
Tampa to Newark flights
West Palm Beach to John F Kennedy Intl flights
West Palm Beach to LaGuardia flights
Jacksonville to John F Kennedy Intl flights
Jacksonville to Newark flights
Fort Myers to John F Kennedy Intl flights
Jacksonville to LaGuardia flights
Fort Myers to Newark flights
Orlando to White Plains flights
Fort Myers to LaGuardia flights
Sarasota to John F Kennedy Intl flights
Pensacola to LaGuardia flights
Orlando to Buffalo flights
Sarasota to Newark flights
Pensacola to John F Kennedy Intl flights
Fort Lauderdale to White Plains flights
Tampa to Islip flights
Sarasota to LaGuardia flights
Pensacola to Newark flights
Orlando to Albany flights
Tampa to White Plains flights
Daytona Beach to John F Kennedy Intl flights
Tampa to Buffalo flights
West Palm Beach to Islip flights
Orlando to Stewart flights
West Palm Beach to White Plains flights
Orlando to Islip flights
Gainesville to Newark flights
Orlando to Syracuse flights
Gainesville to John F Kennedy Intl flights
Panama City to LaGuardia flights
Fort Myers to White Plains flights
Fort Lauderdale to Stewart flights
Orlando to Rochester flights
Fort Lauderdale to Islip flights
Tallahassee to John F Kennedy Intl flights
Fort Lauderdale to Buffalo flights
Fort Lauderdale to Albany flights

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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$78Average$167FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$118Average$194FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$119Average$208FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.