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Stewart

$42+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Aug 2 — Aug 91
Sat 8/2
Sat 8/9
1 adult, Economy
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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 July 28, 2025.

Cheapest airline

American Airlines
On average, American Airlines currently has the cheapest one-way flight from New Windsor Stewart (avg. price of $764).
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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 July 28, 2025.

Fri 10/1011:41 amSWF - FLL
Nonstop3h 31mAllegiant Air
Mon 10/137:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 7/26$96
Fri 9/512:24 pmSWF - MCO
1 stop4h 35mBreeze Airways
Thu 9/118:00 amMCO - SWF
Nonstop2h 53mBreeze Airways
Deal found 7/28$120
Fri 9/512:24 pmSWF - CHS
Nonstop2h 29mBreeze Airways
Mon 9/89:37 amCHS - SWF
Nonstop2h 07mBreeze Airways
Deal found 7/26$122
Sat 8/232:32 pmSWF - MYR
Nonstop1h 58mAllegiant Air
Fri 8/299:30 amMYR - SWF
Nonstop1h 57mAllegiant Air
Deal found 7/27$128
Fri 8/225:36 pmSWF - FLL
Nonstop3h 25mMultiple Airlines
Sun 8/249:45 pmFLL - SWF
1 stop12h 27mMultiple Airlines
Deal found 7/27$152
Fri 8/225:36 pmSWF - MCO
1 stop14h 28mMultiple Airlines
Mon 8/256:20 amMCO - SWF
1 stop10h 26mMultiple Airlines
Deal found 7/26$168
Fri 8/2212:17 pmSWF - MYR
Nonstop1h 58mMultiple Airlines
Sun 8/248:36 pmMYR - SWF
1 stop13h 36mMultiple Airlines
Deal found 7/27$184
Fri 8/157:37 pmSWF - TPA
1 stop11h 56mMultiple Airlines
Fri 8/226:00 amTPA - SWF
1 stop10h 46mMultiple Airlines
Deal found 7/26$194
Fri 10/1711:31 amSWF - MSY
1 stop8h 22mMultiple Airlines
Sun 10/198:22 pmMSY - SWF
1 stop12h 49mMultiple Airlines
Deal found 7/28$208
Fri 8/225:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Sun 8/245:16 pmORD - SWF
1 stop15h 56mMultiple Airlines
Deal found 7/26$225
Fri 8/87:56 pmSWF - CHS
3 stops37h 49mMultiple Airlines
Mon 8/119:38 amCHS - SWF
1 stop9h 28mMultiple Airlines
Deal found 7/26$289
Fri 8/17:56 pmSWF - RDU
2 stops21h 18mMultiple Airlines
Mon 8/49:10 amRDU - SWF
1 stop9h 56mMultiple Airlines
Deal found 7/26$360

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 July 28, 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 11/3

12:01 pm-3:32 pm

Nonstop3h 31m

Fort Lauderdale

Fri 11/7

7:30 am-10:41 am

Nonstop3h 11m

$95

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 9/5

12:24 pm-4:59 pm

1 stop4h 35m

Orlando

Thu 9/11

8:00 am-10:53 am

Nonstop2h 53m

$120

New WindsorCharleston

SWF - CHS

SWFCHS

New Windsor Stewart

Fri 9/5

12:24 pm-2:53 pm

Nonstop2h 29m

Charleston

Mon 9/8

9:37 am-11:44 am

Nonstop2h 07m

$122

New WindsorMyrtle Beach

SWF - MYR

SWFMYR

New Windsor Stewart

Sat 8/23

2:32 pm-4:30 pm

Nonstop1h 58m

Myrtle Beach Intl

Thu 8/28

4:03 pm-6:00 pm

Nonstop1h 57m

$128

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 8/22

5:36 pm-9:01 pm

Nonstop3h 25m

Fort Lauderdale

Sun 8/24

9:45 pm-10:12 am

1 stop12h 27m

$152

New WindsorOrlando

SWF - MCO

SWFMCO

New Windsor Stewart

Fri 8/22

5:36 pm-8:04 am

1 stop14h 28m

Orlando

Mon 8/25

6:20 am-4:46 pm

1 stop10h 26m

$168

New WindsorMyrtle Beach

SWF - MYR

SWFMYR

New Windsor Stewart

Fri 8/22

12:17 pm-2:15 pm

Nonstop1h 58m

Myrtle Beach Intl

Sun 8/24

8:36 pm-10:12 am

1 stop13h 36m

$184

New WindsorTampa

SWF - TPA

SWFTPA

New Windsor Stewart

Fri 8/15

7:37 pm-7:33 am

1 stop11h 56m

Tampa

Fri 8/22

6:00 am-4:46 pm

1 stop10h 46m

$194

New WindsorNew Orleans

SWF - MSY

SWFMSY

New Windsor Stewart

Fri 10/17

11:31 am-6:53 pm

1 stop8h 22m

New Orleans Louis Armstrong

Sun 10/19

8:22 pm-10:11 am

1 stop12h 49m

$208

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 8/22

5:36 pm-10:31 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 40 results
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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 July 25, 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, February is the cheapest month in which you can book a flight from New Windsor (average of $57). Flying from New Windsor in August will prove the most costly (average of $108). 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, Allegiant Air, Frontier. These airlines depart to the following popular destinations: Orlando.

PLAY
PLAY
From $232
Allegiant Air
Allegiant Air
From $75
Breeze Airways
Breeze Airways
From $94
Spirit Airlines
Spirit Airlines
From $30

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 July 28, 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 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
8.0
Very good
190 reviews

Boarding

8.3

Overall

8.0

Entertainment

6.6

Comfort

8.1

Food

6.7

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
190 reviews
Breeze Airways
8.0
Very good
190 reviews

Boarding

8.3

Overall

8.0

Entertainment

6.6

Comfort

8.1

Food

6.7

Crew

8.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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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 July 28, 2025.

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

    This month, the top selected destinations from New Windsor are Reykjavik, Myrtle Beach, Reykjavik Keflavik Intl Airport. Throughout the year, Reykjavik Keflavik Intl Airport, Reykjavik, Myrtle Beach 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 $205 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 Spirit Airlines, Frontier, and Allegiant Air have the cheapest prices from New Windsor. Spirit Airlines flights from New Windsor to Austin Bergstrom ($30), Frontier flights from New Windsor to Orlando ($40), and Allegiant Air flights from New Windsor to Fort Lauderdale ($75).

  • 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 $183
    Fly from New Windsor Stewart to Orlando Airport starting at $203
    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?

    February 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 Tampa from $108 round trip
    Fly from New Windsor to Myrtle Beach from $116 round trip
    Fly from New Windsor to Charleston from $122 round trip
    Fly from New Windsor to Orlando from $126 round trip

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