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Stewart

$99+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SWF
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$193
(Mytrip)

One-way from

$99
(Mytrip)

Popular in

July

Cheapest in

September

Average price

$261
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. 16% potential increase in price ($37 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Mytrip deal was found by Cheapflights users on 7/1. 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 8/85:40 amTPA - SWF
1 stop13h 26mMultiple Airlines
Mon 8/187:37 pmSWF - TPA
1 stop11h 56mMultiple Airlines
Deal found 7/1$193
This CheapOair deal was found by Cheapflights users on 7/3. 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.
Thu 12/41:00 pmTPA - SWF
1 stop22h 44mBreeze Airways
Mon 12/812:24 pmSWF - TPA
1 stop10h 28mBreeze Airways
Deal found 7/3$487

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 July 3, 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

Fri 8/8

5:40 am-7:06 pm

1 stop13h 26m

New Windsor Stewart

Mon 8/18

7:37 pm-7:33 am

1 stop11h 56m

$193

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 12/4

1:00 pm-11:44 am

1 stop22h 44m

New Windsor Stewart

Mon 12/8

12:24 pm-10:52 pm

1 stop10h 28m

$487

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Mon 7/28

5:40 am-7:06 pm

1 stop13h 26m

$99

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 8/24

1:17 pm-12:48 pm

1 stop23h 31m

$292

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 August is currently the most expensive (average of $222). 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 July 3, 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 July 3, 2025.
Read reviews from past customers who have flown Breeze Airways from Clearwater to New Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Entertainment

6.6

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Boarding

8.3

Entertainment

6.6

Comfort

8.2

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $70. While the most popular route (Tampa - New Windsor Stewart) can be booked for $194 on average our data indicates $155 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 August is currently the most expensive (average of $222). 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 Clearwater?

Book flights to Clearwater if you plan to visit one of these locations
Kingston

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$58Average$190FlexibilityNo cancel feeOn-time62%
Allegiant AirCheapest$74Average$159FlexibilityNo cancel feeOn-time88%
Breeze AirwaysCheapest$117Average$215FlexibilityNo cancel feeOn-timeN/A

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