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Clearwater

$73+ Cheap flights from New Windsor (SWF) to Clearwater, FL

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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Stewart to Clearwater

Cheapest flights from Stewart to Clearwater
Explore the most affordable flight options available from Stewart to Clearwater. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Wed 12/315:34 pmSWF - TPA
2 stops18h 32mMultiple Airlines
Sun 1/47:15 amTPA - SWF
1 stop10h 23mMultiple Airlines
Deal found 12/21$510
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/216:28 pmSWF - TPA
1 stop21h 28mMultiple Airlines
Fri 1/27:10 amTPA - SWF
1 stop10h 46mMultiple Airlines
Deal found 12/21$535
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/228:25 pmSWF - TPA
1 stop11h 11mMultiple Airlines
Thu 12/259:03 pmTPA - SWF
1 stop14h 04mMultiple Airlines
Deal found 12/21$548
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/228:25 pmSWF - TPA
1 stop20h 43mMultiple Airlines
Fri 1/27:10 amTPA - SWF
1 stop10h 46mMultiple Airlines
Deal found 12/21$642
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:34 pmSWF - TPA
2 stops18h 32mMultiple Airlines
Fri 1/27:10 amTPA - SWF
1 stop10h 46mMultiple Airlines
Deal found 12/22$698
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/245:34 pmSWF - TPA
2 stops18h 32mMultiple Airlines
Sun 1/47:15 amTPA - SWF
1 stop10h 23mMultiple Airlines
Deal found 12/22$730
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:28 pmSWF - TPA
2 stops25h 40mMultiple Airlines
Fri 12/267:10 amTPA - SWF
1 stop10h 46mMultiple Airlines
Deal found 12/22$801
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Fri 12/2612:24 pmSWF - TPA
1 stop10h 28mMultiple Airlines
Wed 12/319:03 pmTPA - SWF
2 stops38h 41mMultiple Airlines
Deal found 12/20$899
This Booking.com deal was found by Cheapflights users on 12/21. 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.
Mon 12/2912:24 pmSWF - TPA
1 stop10h 28mBreeze Airways
Sun 1/41:00 pmTPA - SWF
1 stop22h 44mBreeze Airways
Deal found 12/21$925

Find flight deals from Stewart to Clearwater

Keep the following information in mind while searching for Stewart to Clearwater flight deals. Data was last updated December 23, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$167
(CheapOair)

One-way from

$73
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$507
Provider with most accurate pricing for New York (NYC)-Tampa flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Tampa flights.
Search Deals
From New Windsor Stewart to Clearwater
Search Deals
One-way flight from New Windsor Stewart to Clearwater
Search Deals
Highest demand for flights based on searches. 31% potential increase in price ($87 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($29 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Clearwater 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 December 23, 2025.
Use the filters below to find and compare flights from New Windsor to Clearwater that are best for you.

Fly from

Stewart

Fly to

Clearwater

Route

Depart

Return

Price

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Fri 1/30

11:09 am-5:33 pm

1 stop6h 24m

Tampa

Sun 2/1

6:55 pm-10:19 am

1 stop15h 24m

$199

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Fri 1/9

12:11 pm-9:57 pm

1 stop9h 46m

Tampa

Thu 1/15

8:38 am-11:31 am

2 stops26h 53m

$238

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Mon 1/12

11:09 am-8:20 am

1 stop21h 11m

Tampa

Thu 1/15

10:05 am-5:59 pm

1 stop7h 54m

$241

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Mon 1/5

11:37 am-7:36 am

1 stop19h 59m

Tampa

Thu 1/8

10:24 pm-6:43 pm

2 stops20h 19m

$251

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Sun 1/11

6:49 pm-7:51 pm

1 stop25h 02m

Tampa

Thu 1/15

8:38 am-11:31 am

2 stops26h 53m

$267

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Thu 1/8

6:49 pm-7:51 pm

1 stop25h 02m

Tampa

Sun 1/11

9:47 pm-10:19 am

1 stop12h 32m

$271

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Mon 2/16

12:11 pm-9:57 pm

1 stop9h 46m

Tampa

Thu 2/19

6:35 pm-10:14 am

2 stops15h 39m

$316

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Fri 1/9

12:11 pm-9:57 pm

1 stop9h 46m

Tampa

Mon 1/12

8:20 am-6:43 pm

2 stops10h 23m

$316

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Mon 1/12

11:09 am-5:33 pm

1 stop6h 24m

$73

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Sat 5/16

12:05 pm-4:21 pm

1 stop4h 16m

$83

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 17 results
1
2

Best time to book a flight from Stewart to Clearwater

Have a flexible travel schedule? Discover the best time to fly to Clearwater from Stewart 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 New Windsor to Clearwater

What is the cheapest month to book a flight from New Windsor to Clearwater?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Clearwater (average of $29). Flying from New Windsor to Clearwater in July is currently the most expensive (average of $78). 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 SWF to CL9?

Find hourly flight availability from Stewart to Clearwater. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

It’s optimal to fly from New Windsor to Clearwater in the afternoon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight at noon.

Reviews of airlines servicing Clearwater

Get insights into the airlines that provide service to Clearwater. 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 Clearwater. Reviews last updated December 23, 2025.
Get a feel of what it's like to fly with JetBlue, Allegiant Air, and Frontier from New Windsor to Clearwater by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,897 reviews

Boarding

7.4

Crew

8.0

Comfort

7.6

Food

6.7

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,897 reviews
JetBlue
7.2
Good
2,897 reviews

Boarding

7.4

Crew

8.0

Comfort

7.6

Food

6.7

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
Allegiant Air
7.2
Good
701 reviews
JetBlue
7.2
Good
2,897 reviews

Boarding

7.4

Crew

8.0

Comfort

7.6

Food

6.7

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
Frontier
5.8
Fair
3,075 reviews
JetBlue
7.2
Good
2,897 reviews

Boarding

7.4

Crew

8.0

Comfort

7.6

Food

6.7

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Clearwater. 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 from for flights from New Windsor to Clearwater?

    For a flight from New Windsor to Clearwater, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 outbound flights to Clearwater per day. 5 airlines have flights to Clearwater from New Windsor Stewart on a regular basis.

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

    Looking for the cheapest flight from New Windsor to Clearwater? While on average our users pay $203, our data indicates the cheapest price to be $59. The most popular route (New Windsor Stewart - Tampa), is priced around $191.

  • Can I find deals for flights from Stewart to Clearwater that include hotel bookings?

    Yes. In addition to deals on Stewart to Clearwater flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Clearwater?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Clearwater.

  • Can I find deals for business class flights from Stewart to Clearwater?

    Yes. Cheapflights offers flight deals from Stewart to Clearwater 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 New Windsor to Clearwater?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Clearwater (average of $29). Flying from New Windsor to Clearwater in July is currently the most expensive (average of $78). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from Stewart to Clearwater

Discover the top 5 airlines that operate flights from Stewart to Clearwater. 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$40Average$93FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$67Average$142FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$76Average$163FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$111Average$231FlexibilityNo cancel feeOn-time62%
Breeze AirwaysCheapest$120Average$234FlexibilityNo cancel feeOn-timeN/A

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