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Stewart

$97+ Cheap flights from Tampa to New Windsor (TPA - 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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
TPA — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Tampa to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Tampa (TPA) to Stewart (SWF). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 11, 2025.

Round-trip from

$274
(Kiwi.com)

One-way from

$97
(Kiwi.com)

Popular in

July

Cheapest in

September

Average price

$88
From Tampa to New Windsor Stewart
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One-way flight from Tampa to New Windsor Stewart
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Highest demand for flights based on searches. 17% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Tampa to Stewart

Cheapest flights from Tampa to Stewart
Explore the most affordable flight options available from Tampa to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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 12/48:27 pmTPA - SWF
1 stop15h 10mMultiple Airlines
Mon 12/812:27 pmSWF - TPA
1 stop19h 47mMultiple Airlines
Deal found 9/9$217
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 11/208:27 pmTPA - SWF
1 stop13h 55mMultiple Airlines
Mon 11/2410:57 amSWF - TPA
1 stop11h 21mMultiple Airlines
Deal found 9/10$274
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/57:15 amTPA - SWF
1 stop9h 40mMultiple Airlines
Mon 10/611:01 amSWF - TPA
1 stop6h 18mMultiple Airlines
Deal found 9/9$282
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 10/267:15 amTPA - SWF
1 stop9h 40mMultiple Airlines
Sun 11/21:35 pmSWF - TPA
1 stop26h 21mMultiple Airlines
Deal found 9/11$312
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/43:08 pmTPA - SWF
2 stops19h 55mMultiple Airlines
Mon 10/611:01 amSWF - TPA
1 stop20h 07mMultiple Airlines
Deal found 9/9$321
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 11/202:35 pmTPA - SWF
1 stop19h 47mMultiple Airlines
Mon 12/15:49 pmSWF - TPA
2 stops28h 29mMultiple Airlines
Deal found 9/9$359
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 12/217:15 amTPA - SWF
1 stop10h 23mMultiple Airlines
Mon 1/512:24 pmSWF - TPA
1 stop10h 28mMultiple Airlines
Deal found 9/9$372
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 12/198:10 amTPA - SWF
2 stops24h 45mMultiple Airlines
Sun 1/46:28 pmSWF - TPA
1 stop21h 28mMultiple Airlines
Deal found 9/11$399

Cheapflights Fare Finder

 
Customize your flight search to find flights from Tampa 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 September 11, 2025.
Use the filters below to find and compare flights from Tampa to New Windsor that are best for you.

Fly from

Tampa

Fly to

Stewart

Route

Depart

Return

Price

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 12/4

8:27 pm-11:37 am

1 stop15h 10m

New Windsor Stewart

Mon 12/8

12:27 pm-8:14 am

1 stop19h 47m

$217

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 10/5

7:15 am-4:55 pm

1 stop9h 40m

New Windsor Stewart

Mon 10/6

11:01 am-5:19 pm

1 stop6h 18m

$282

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sat 10/4

3:08 pm-11:03 am

2 stops19h 55m

New Windsor Stewart

Mon 10/6

11:01 am-7:08 am

1 stop20h 07m

$321

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Thu 11/20

2:35 pm-10:22 am

1 stop19h 47m

New Windsor Stewart

Mon 12/1

5:49 pm-10:18 pm

2 stops28h 29m

$359

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 10/26

8:41 pm-2:11 pm

2 stops17h 30m

New Windsor Stewart

Sun 11/2

1:35 pm-10:01 am

2 stops20h 26m

$397

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 12/19

8:10 am-8:55 am

2 stops24h 45m

New Windsor Stewart

Sun 1/4

6:28 pm-3:56 pm

1 stop21h 28m

$399

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Sun 12/21

7:15 am-5:38 pm

1 stop10h 23m

New Windsor Stewart

Sun 1/4

6:28 pm-3:56 pm

1 stop21h 28m

$408

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Fri 12/19

8:10 am-8:55 am

2 stops24h 45m

New Windsor Stewart

Fri 1/2

12:24 pm-10:52 pm

1 stop10h 28m

$413

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Mon 12/22

6:30 am-7:35 pm

2 stops13h 05m

New Windsor Stewart

Sun 1/4

6:28 pm-3:56 pm

1 stop21h 28m

$451

TampaNew Windsor

TPA - SWF

TPASWF

Tampa

Mon 12/22

6:46 am-7:35 pm

1 stop12h 49m

New Windsor Stewart

Mon 1/5

12:24 pm-10:52 pm

1 stop10h 28m

$476

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 21 results
1
2
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Best time to book a flight from Tampa to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from Tampa to New Windsor (average of $109). Flying from Tampa to New Windsor in December is currently the most expensive (average of $202). 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 TPA to SWF?

Find hourly flight availability from Tampa 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 September 11, 2025.

It’s typically best to fly out from Tampa to New Windsor in the morning. Doing so could potentially save you 6% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 September 11, 2025.
Get a feel of what it's like to fly with JetBlue and Allegiant Air from Tampa to New Windsor 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
2,913 reviews

Crew

8.0

Overall

7.2

Entertainment

7.3

Comfort

7.6

Food

6.7

Boarding

7.4

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
2,913 reviews
JetBlue
7.2
Good
2,913 reviews

Crew

8.0

Overall

7.2

Entertainment

7.3

Comfort

7.6

Food

6.7

Boarding

7.4

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
702 reviews
JetBlue
7.2
Good
2,913 reviews

Crew

8.0

Overall

7.2

Entertainment

7.3

Comfort

7.6

Food

6.7

Boarding

7.4

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 Tampa to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Tampa to New Windsor round-trip?

    Flying on Allegiant Air is currently your cheapest option to New Windsor, with prices starting at $123. Another option worth looking into is JetBlue, starting at $126 round trip. You may be able to fly from Tampa to New Windsor for 34% less than the average price by searching for these airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Tampa 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 Tampa to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Tampa to New Windsor (average of $109). Flying from Tampa to New Windsor in December is currently the most expensive (average of $202). 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 Tampa to Stewart

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Top 2 airlines flying from Tampa to Stewart

Discover the top 2 airlines that operate flights from Tampa 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Allegiant AirCheapest$123Average$186FlexibilityNo cancel feeOn-time88%
JetBlueCheapest$126Average$197FlexibilityNo cancel feeOn-time62%

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