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Stewart

$33+ Cheap flights from New Windsor

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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — FLL
Jul 14 — Jul 211
Tue 7/14
Tue 7/21
1 adult, Economy
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Find flights from Stewart within your budget

 
Find flights departing from Stewart that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on June 14, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Sun 7/26

10:28 am-1:37 pm

Nonstop3h 09m

Fort Lauderdale

Sun 8/2

6:30 am-9:38 am

Nonstop3h 08m

$94

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Sun 7/26

10:28 am-1:37 pm

Nonstop3h 09m

Fort Lauderdale

Thu 7/30

6:30 am-9:38 am

Nonstop3h 08m

$96
Quickest round-trip

New WindsorRaleigh

SWF - RDU

SWFRDU

New Windsor Stewart

Sat 7/25

12:05 pm-1:45 pm

Nonstop1h 40m

Raleigh-Durham

Sat 8/1

9:45 am-11:25 am

Nonstop1h 40m

$127

New WindsorRaleigh

SWF - RDU

SWFRDU

New Windsor Stewart

Wed 8/19

12:05 pm-1:45 pm

Nonstop1h 40m

Raleigh-Durham

Wed 8/26

9:45 am-11:25 am

Nonstop1h 40m

$128

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Sun 8/9

10:28 am-1:37 pm

Nonstop3h 09m

Fort Lauderdale

Sun 8/16

6:30 am-9:38 am

Nonstop3h 08m

$154

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Sat 9/5

12:05 pm-4:26 pm

1 stop4h 21m

Tampa

Sat 9/12

7:00 am-11:39 am

1 stop4h 39m

$162

New WindsorRaleigh

SWF - RDU

SWFRDU

New Windsor Stewart

Sat 7/18

12:05 pm-1:45 pm

Nonstop1h 40m

Raleigh-Durham

Wed 7/22

9:45 am-11:25 am

Nonstop1h 40m

$163

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Thu 7/9

10:28 am-1:37 pm

Nonstop3h 09m

Fort Lauderdale

Thu 7/16

6:30 am-9:38 am

Nonstop3h 08m

$174

New WindsorMyrtle Beach

SWF - MYR

SWFMYR

New Windsor Stewart

Fri 7/10

5:49 pm-7:52 pm

Nonstop2h 03m

Myrtle Beach Intl

Fri 7/17

3:03 pm-4:59 pm

Nonstop1h 56m

$182

New WindsorMyrtle Beach

SWF - MYR

SWFMYR

New Windsor Stewart

Thu 8/27

6:16 pm-8:22 pm

Nonstop2h 06m

Myrtle Beach Intl

Mon 8/31

11:00 am-12:54 pm

Nonstop1h 54m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 60 resultsSorted by cheapest first
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Compare providers for flights from Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart in June
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
OvagoPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: Among all the travel providers offering deals on flights from New Windsor, FlightHub has been found to have the most accurate pricing. Users can find the same prices on deals on Cheapflights as FlightHub about >95% of the time. This is based on searches for flights from New Windsor made on Cheapflights over the past month and is updated monthly.
  • Most trusted provider: In terms of trustworthiness, Cheapflights users rate FlightHub the highest out of those offering flight deals from New Windsor. FlightHub has a user feedback rating of 3 out of 3 stars (3 being the best) and has received the most positive sentiment from Cheapflights users searching for flights from New Windsor. This info is gathered from Cheapflights searches over the past month.

Best time to book a flight from Stewart

Have a flexible travel schedule? Discover the best time to fly 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.

Travel insights for flights from Stewart

Get recent, data-driven insights about flights from Stewart including ideal travel times, pricing trends, and more.

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

Currently, October is the cheapest month in which you can book a flight from New Windsor (average of $100). Flying from New Windsor in November will prove the most costly (average of $246). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from New Windsor?

For flights departing from New Windsor check dates and pricing for the following: Allegiant Air, JetBlue. These airlines depart to the following popular destinations: Fort Lauderdale.

Allegiant Air
Allegiant Air
From $49
Breeze Airways
Breeze Airways
From $108
JetBlue
JetBlue
From $79
Icelandair
Icelandair
From $368

When is the best time to book a flight from New Windsor?

To ensure you get the cheapest price possible for a flight from New Windsor, you should look to book at least 14 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

Airline reviews for flights from Stewart

Read reviews and ratings of airlines operating flights from Stewart. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Stewart travel. Please note that the reviews are sourced from user searches and were last updated on June 14, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Get a feel of what it's like to fly with Allegiant Air and JetBlue from New Windsor by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.3
Good
700 reviews

Entertainment

5.4

Comfort

6.9

Overall

7.3

Food

5.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Elizabeth,Jun 2026

LAS - RAP

Amazing the only thing I would change is the price gouging. They do for the checked bag or the carry on bag. It's a little absurd. I'm already paying them $500. And I can't take a carry on?!
Allegiant Air
7.3
Good
700 reviews
Allegiant Air
7.3
Good
700 reviews

Entertainment

5.4

Comfort

6.9

Overall

7.3

Food

5.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Elizabeth,Jun 2026

LAS - RAP

Amazing the only thing I would change is the price gouging. They do for the checked bag or the carry on bag. It's a little absurd. I'm already paying them $500. And I can't take a carry on?!
JetBlue
7.1
Good
2,982 reviews
Allegiant Air
7.3
Good
700 reviews

Entertainment

5.4

Comfort

6.9

Overall

7.3

Food

5.8

Boarding

7.6

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Elizabeth,Jun 2026

LAS - RAP

Amazing the only thing I would change is the price gouging. They do for the checked bag or the carry on bag. It's a little absurd. I'm already paying them $500. And I can't take a carry on?!

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Related info for your journey

Access useful and relevant information related to your journey from Stewart. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated June 14, 2026.

  • What are the most popular destinations to fly to from New Windsor?

    This month, the top selected destinations from New Windsor are Myrtle Beach, Fort Lauderdale, Tampa. Throughout the year, Myrtle Beach, Fort Lauderdale, Orlando are some of the top choices made by users flying from New Windsor.

  • What is the cheapest flight from New Windsor to anywhere?

    Users have flown out of New Windsor for as low as $54 to Orlando Sanford Intl Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $180 to fly from New Windsor.

  • What are the cheapest airlines flying from New Windsor to anywhere?

    Over the past few days, we've found that Allegiant Air, JetBlue, and Breeze Airways have the cheapest prices from New Windsor. Allegiant Air flights from New Windsor to Fort Lauderdale ($49), JetBlue flights from New Windsor to Fort Lauderdale ($79), and Breeze Airways flights from New Windsor to Charleston ($108).

  • What is the cheapest premium economy flight from New Windsor?

    Options for some of the cheapest premium economy flights from New Windsor we have found on Cheapflights are as follows:
    Fly from New Windsor Stewart to Charleston starting at $158
    Fly from New Windsor Stewart to Raleigh starting at $223
    Fly from New Windsor Stewart to Orlando Airport starting at $248

  • What is the cheapest month to fly from New Windsor?

    October is currently the cheapest month to fly from New Windsor. At this moment in time November is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from New Windsor?

    Check out the cheapest flights from New Windsor to embark to:
    Fly from New Windsor to Fort Lauderdale from $83 round trip
    Fly from New Windsor to Charleston from $103 round trip
    Fly from New Windsor to Raleigh from $112 round trip
    Fly from New Windsor to Orlando from $127 round trip
    Fly from New Windsor to Tampa from $138 round trip

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