HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$44+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Jan 14 — Jan 211
Wed 1/14
Wed 1/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

What to know about flights from Stewart

Discover essential information about flights departing from Stewart, including flight schedules, destinations, airlines operating at the Stewart airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated December 15, 2025.

Cheapest airline

American Airlines
On average, American Airlines currently has the cheapest one-way flight from New Windsor Stewart (avg. price of $253).
Search Deals

Find flights from Stewart

Cheapest flights from Stewart
Explore the most affordable flight options available from Stewart. Find the lowest fares based on data from user searches, with prices last updated on December 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/13. 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 1/511:37 amSWF - FLL
Nonstop3h 13mAllegiant Air
Mon 1/127:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/13$91
This Kiwi.com deal was found by Cheapflights users on 12/15. 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 1/3011:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Mon 2/27:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/15$95
This Cheapflightsfares deal was found by Cheapflights users on 12/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/2611:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Fri 1/307:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/15$96
This Kiwi.com deal was found by Cheapflights users on 12/13. 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 1/911:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Fri 1/167:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/13$99
This eDestinos deal was found by Cheapflights users on 12/14. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2311:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Mon 1/267:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/14$102
This Kiwi.com deal was found by Cheapflights users on 12/14. 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 1/911:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Mon 1/127:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/14$103
This Kissandfly.com deal was found by Cheapflights users on 12/15. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/1911:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Fri 1/237:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/15$105
This Booking.com deal was found by Cheapflights users on 12/14. 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 1/1211:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Fri 1/167:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 12/14$108
This Mytrip deal was found by Cheapflights users on 12/12. 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.
Sun 2/2211:52 amSWF - FLL
Nonstop3h 17mAllegiant Air
Sun 3/18:00 amFLL - SWF
Nonstop3h 02mAllegiant Air
Deal found 12/12$109
This CheapOair deal was found by Cheapflights users on 12/14. 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.
Mon 2/212:11 pmSWF - MCO
1 stop4h 38mBreeze Airways
Fri 2/67:15 amMCO - SWF
1 stop4h 16mBreeze Airways
Deal found 12/14$111
This CheapOair deal was found by Cheapflights users on 12/13. 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.
Mon 1/1912:11 pmSWF - MCO
1 stop4h 38mBreeze Airways
Fri 1/237:15 amMCO - SWF
1 stop4h 16mBreeze Airways
Deal found 12/13$114
This Breeze Airways deal was found by Cheapflights users on 12/14. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/212:11 pmSWF - MCO
1 stop4h 38mBreeze Airways
Thu 2/58:10 amMCO - SWF
Nonstop2h 58mBreeze Airways
Deal found 12/14$115

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 December 15, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Orlando

Route

Depart

Return

Price

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 1/26

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 1/30

7:15 am-10:19 am

Nonstop3h 04m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 2/2

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Sun 2/15

7:50 am-10:52 am

Nonstop3h 02m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 1/5

11:37 am-2:50 pm

Nonstop3h 13m

Fort Lauderdale

Fri 1/9

7:15 am-10:19 am

Nonstop3h 04m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 1/19

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 1/23

7:15 am-10:19 am

Nonstop3h 04m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/9

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 1/16

7:15 am-10:19 am

Nonstop3h 04m

$99

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/30

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Mon 2/2

7:15 am-10:19 am

Nonstop3h 04m

$100

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/23

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Mon 1/26

7:15 am-10:19 am

Nonstop3h 04m

$102

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 2/6

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Mon 2/9

7:15 am-10:19 am

Nonstop3h 04m

$104

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 1/23

11:09 am-2:52 pm

Nonstop3h 43m

Fort Lauderdale

Fri 1/30

7:15 am-10:19 am

Nonstop3h 04m

$104

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Mon 2/2

12:11 pm-4:49 pm

1 stop4h 38m

Orlando

Fri 2/6

7:15 am-11:31 am

1 stop4h 16m

$111

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/14

Showing 1-10 of 60 results
1
2
3
...
6

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 December
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
OvagoPrice Accuracy2 starsTrust Score*2 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 Expedia the highest out of those offering flight deals from New Windsor. Expedia 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.

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

Use this chart to determine the optimal time to book a round-trip flight from Stewart to Orlando. Price data was last updated on December 12, 2025.

To ensure you get the cheapest price possible for a flight from New Windsor, you should look to book at least 40 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.

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

Currently, September is the cheapest month in which you can book a flight from New Windsor (average of $43). Flying from New Windsor in August will prove the most costly (average of $91). 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: Breeze Airways, Spirit Airlines, JetBlue, Frontier. These airlines depart to the following popular destinations: Orlando.

Allegiant Air
Allegiant Air
From $76
Breeze Airways
Breeze Airways
From $88
Spirit Airlines
Spirit Airlines
From $61
JetBlue
JetBlue
From $111

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 December 15, 2025. 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 Breeze Airways, JetBlue, and Spirit Airlines 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.
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Boarding

8.4

Overall

8.2

Entertainment

6.7

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Breeze Airways
8.2
Very good
248 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Boarding

8.4

Overall

8.2

Entertainment

6.7

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
JetBlue
7.2
Good
2,895 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Boarding

8.4

Overall

8.2

Entertainment

6.7

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Spirit Airlines
6.3
Okay
8,188 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Boarding

8.4

Overall

8.2

Entertainment

6.7

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.
Frontier
5.8
Fair
3,081 reviews
Breeze Airways
8.2
Very good
248 reviews

Crew

8.8

Boarding

8.4

Overall

8.2

Entertainment

6.7

Comfort

8.2

Food

6.7

Reviews

1 / 16
10.0
Excellent

Anonymous,Dec 2025

RSW - ISP

There was no food offered so I had to just put okay. Other than that all was great.

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.

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 December 15, 2025.

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

    This month, the top selected destinations from New Windsor are Fort Lauderdale, Orlando, Punta Gorda. Throughout the year, Reykjavik Keflavik Intl Airport, Reykjavik, Fort Lauderdale 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 $48 to Orlando Sanford Intl Airport (prices may vary depending on the airline and departure time). On average, users have booked flights for $239 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 Frontier, Spirit Airlines, and Allegiant Air have the cheapest prices from New Windsor. Frontier flights from New Windsor to Orlando ($40), Spirit Airlines flights from New Windsor to Charlotte Douglas ($61), and Allegiant Air flights from New Windsor to Fort Lauderdale ($76).

  • 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 Orlando Airport starting at $193
    Fly from New Windsor Stewart to Reykjavik Keflavik Intl Airport starting at $595

  • What is the cheapest first class flight from New Windsor?

    If you’re looking for a cheap first-class flight from New Windsor, consider Reykjavik. Prices start at $598 so you can fly first-class even on a budget.

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

    September is currently the cheapest month to fly from New Windsor. At this moment in time August 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 $95 round trip
    Fly from New Windsor to Myrtle Beach from $110 round trip
    Fly from New Windsor to Orlando from $122 round trip
    Fly from New Windsor to Charleston from $122 round trip
    Fly from New Windsor to Tampa from $130 round trip

See more FAQs

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.