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Stewart

$39+ Cheap flights from New Windsor

SWF — MCO
Nov 25 — Dec 21
Wed 11/25
Wed 12/2
1 adult, Economy
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Find flights from Stewart within your budget

 

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorFort Lauderdale

SWF New Windsor Stewart - FLL Fort Lauderdale

SWFFLL

New Windsor Stewart

Sun 12/6

6:49 pm-10:12 pm

Nonstop3h 23m

Fort Lauderdale

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$41

New WindsorFort Lauderdale

SWF New Windsor Stewart - FLL Fort Lauderdale

SWFFLL

New Windsor Stewart

Sun 1/17

12:25 pm-4:02 pm

Nonstop3h 37m

Fort Lauderdale

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$47
Quickest round-trip

New WindsorRaleigh

SWF New Windsor Stewart - RDU Raleigh-Durham

SWFRDU

New Windsor Stewart

Sat 12/12

12:39 pm-2:19 pm

Nonstop1h 40m

Raleigh-Durham

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$48

New WindsorOrlando

SWF New Windsor Stewart - SFB Orlando Sanford Intl

SWFSFB

New Windsor Stewart

Mon 11/16

7:04 pm-9:53 pm

Nonstop2h 49m

Orlando Sanford Intl

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$55

New WindsorCharleston

SWF New Windsor Stewart - CHS Charleston

SWFCHS

New Windsor Stewart

Fri 1/15

11:58 am-2:29 pm

Nonstop2h 31m

Charleston

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$58

New WindsorRaleigh

SWF New Windsor Stewart - RDU Raleigh-Durham

SWFRDU

New Windsor Stewart

Wed 11/18

12:39 pm-2:19 pm

Nonstop1h 40m

Raleigh-Durham

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$60

New WindsorFort Lauderdale

SWF New Windsor Stewart - FLL Fort Lauderdale

SWFFLL

New Windsor Stewart

Thu 12/10

6:49 pm-10:12 pm

Nonstop3h 23m

Fort Lauderdale

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$62

New WindsorCharleston

SWF New Windsor Stewart - CHS Charleston

SWFCHS

New Windsor Stewart

Fri 12/18

12:16 pm-2:47 pm

Nonstop2h 31m

Charleston

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$64

New WindsorRaleigh

SWF New Windsor Stewart - RDU Raleigh-Durham

SWFRDU

New Windsor Stewart

Sat 11/7

12:39 pm-2:19 pm

Nonstop1h 40m

Raleigh-Durham

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$79

New WindsorOrlando

SWF New Windsor Stewart - MCO Orlando

SWFMCO

New Windsor Stewart

Wed 11/18

12:39 pm-5:12 pm

1 stop4h 33m

Orlando

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$81

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart in October
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
GotogatePrice Accuracy2 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy2 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

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, May is the cheapest month in which you can book a flight from New Windsor (average of $213). Flying from New Windsor in February will prove the most costly (average of $337). 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, JetBlue, Frontier. These airlines depart to the following popular destinations: Orlando.

Allegiant Air
Allegiant Air
From $49
Breeze Airways
Breeze Airways
From $97
JetBlue
JetBlue
From $108
Frontier
Frontier
From $68

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 33 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

Get a feel of what it's like to fly with Breeze Airways,JetBlue, andFrontier 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
324 reviews

Overall

8.2

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Breeze Airways
8.2
Very good
324 reviews
Breeze Airways
8.2
Very good
324 reviews

Overall

8.2

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
JetBlue
7.1
Good
3,066 reviews
Breeze Airways
8.2
Very good
324 reviews

Overall

8.2

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.
Frontier
5.5
Fair
2,516 reviews
Breeze Airways
8.2
Very good
324 reviews

Overall

8.2

Crew

8.8

Entertainment

6.8

Boarding

8.4

Comfort

8.2

Food

6.7

Reviews

1 / 18
10.0
Excellent

James,Oct 2026

RSW - RDU

The plane was clean and modern. The crew was excellent. The flight left early and arrived ~ 30 mintues early. As such, our bags were delayed in arriving. Food (snacks) were average.

Browse thousands of different options on Cheapflights for your next trip

Related info for your journey

  • 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, Orlando Airport. Throughout the year, Fort Lauderdale, Myrtle Beach, Orlando Airport 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 $40 to Fort Lauderdale (prices may vary depending on the airline and departure time). On average, users have booked flights for $213 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, Frontier, and Breeze Airways have the cheapest prices from New Windsor. Allegiant Air flights from New Windsor to Fort Lauderdale ($49), Frontier flights from New Windsor to Atlanta Hartsfield-Jackson ($68), and Breeze Airways flights from New Windsor to Charleston ($97).

  • 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 $239
    Fly from New Windsor Stewart to Raleigh starting at $337

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

    May is currently the cheapest month to fly from New Windsor. At this moment in time February 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 $92 round trip
    Fly from New Windsor to Raleigh from $97 round trip
    Fly from New Windsor to Myrtle Beach from $106 round trip
    Fly from New Windsor to Charleston from $106 round trip
    Fly from New Windsor to Tampa from $112 round trip

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