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Stewart

$46+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MCO
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Cheapest airline

American Airlines
On average, American Airlines currently has the cheapest one-way flight from New Windsor Stewart (avg. price of $742).
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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 September 11, 2025.

Mon 11/1012:01 pmSWF - FLL
Nonstop3h 31mAllegiant Air
Fri 11/147:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/10$92
Fri 10/312:11 pmSWF - FLL
Nonstop3h 31mAllegiant Air
Mon 10/67:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/10$94
Fri 10/312:11 pmSWF - FLL
Nonstop3h 31mAllegiant Air
Fri 10/107:40 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/10$95
Fri 10/1711:31 amSWF - FLL
Nonstop3h 31mAllegiant Air
Mon 10/207:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/10$100
Fri 11/1411:01 amSWF - FLL
Nonstop3h 31mAllegiant Air
Mon 11/178:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/11$102
Tue 10/711:16 amSWF - PIE
Nonstop3h 00mAllegiant Air
Tue 10/147:40 amPIE - SWF
Nonstop2h 46mAllegiant Air
Deal found 9/9$104
Mon 10/1311:01 amSWF - FLL
Nonstop3h 31mAllegiant Air
Mon 10/207:00 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/10$104
Fri 1/911:09 amSWF - FLL
Nonstop3h 43mAllegiant Air
Mon 1/127:15 amFLL - SWF
Nonstop3h 04mAllegiant Air
Deal found 9/11$105
Fri 10/3111:31 amSWF - FLL
Nonstop3h 31mAllegiant Air
Fri 11/77:30 amFLL - SWF
Nonstop3h 11mAllegiant Air
Deal found 9/11$107
Sun 10/267:11 pmSWF - PIE
Nonstop3h 00mAllegiant Air
Sun 11/22:38 pmPIE - SWF
Nonstop2h 48mAllegiant Air
Deal found 9/11$108
Fri 11/2111:12 amSWF - FLL
Nonstop3h 06mAllegiant Air
Wed 11/268:20 amFLL - SWF
Nonstop3h 07mAllegiant Air
Deal found 9/11$109
Thu 11/61:32 pmSWF - MYR
Nonstop2h 01mAllegiant Air
Sun 11/910:50 amMYR - SWF
Nonstop1h 52mAllegiant Air
Deal found 9/9$113

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 September 11, 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 10/20

11:01 am-2:32 pm

Nonstop3h 31m

Fort Lauderdale

Fri 10/24

7:30 am-10:41 am

Nonstop3h 11m

$94

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 10/31

11:31 am-3:02 pm

Nonstop3h 31m

Fort Lauderdale

Fri 11/7

7:30 am-10:41 am

Nonstop3h 11m

$94

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 12/5

12:27 pm-3:40 pm

Nonstop3h 13m

Fort Lauderdale

Mon 12/15

8:30 am-11:37 am

Nonstop3h 07m

$94

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 10/24

11:31 am-3:02 pm

Nonstop3h 31m

Fort Lauderdale

Fri 10/31

7:30 am-10:41 am

Nonstop3h 11m

$94

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Mon 11/17

12:01 pm-3:32 pm

Nonstop3h 31m

Fort Lauderdale

Fri 11/21

7:15 am-10:22 am

Nonstop3h 07m

$95

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 10/31

11:31 am-3:02 pm

Nonstop3h 31m

Fort Lauderdale

Mon 11/3

8:00 am-11:11 am

Nonstop3h 11m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 10/3

12:11 pm-3:42 pm

Nonstop3h 31m

Fort Lauderdale

Fri 10/10

7:40 am-10:51 am

Nonstop3h 11m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 10/3

12:11 pm-3:42 pm

Nonstop3h 31m

Fort Lauderdale

Mon 10/13

7:00 am-10:11 am

Nonstop3h 11m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 11/14

11:01 am-2:32 pm

Nonstop3h 31m

Fort Lauderdale

Mon 11/17

8:00 am-11:11 am

Nonstop3h 11m

$96

New WindsorFort Lauderdale

SWF - FLL

SWFFLL

New Windsor Stewart

Fri 12/5

12:27 pm-3:40 pm

Nonstop3h 13m

Fort Lauderdale

Mon 12/8

8:30 am-11:37 am

Nonstop3h 07m

$96

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 60 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 August 29, 2025.

To ensure you get the cheapest price possible for a flight from New Windsor, you should look to book at least 65 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 $58). Flying from New Windsor in December will prove the most costly (average of $100). 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 $250
Allegiant Air
Allegiant Air
From $76
Breeze Airways
Breeze Airways
From $88
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 September 11, 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 Allegiant Air 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
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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
205 reviews
Breeze Airways
8.0
Very good
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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!
JetBlue
7.2
Good
2,913 reviews
Breeze Airways
8.0
Very good
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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!
Allegiant Air
7.2
Good
702 reviews
Breeze Airways
8.0
Very good
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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!
Spirit Airlines
6.3
Okay
8,023 reviews
Breeze Airways
8.0
Very good
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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!
Frontier
5.8
Fair
3,177 reviews
Breeze Airways
8.0
Very good
205 reviews

Comfort

8.1

Entertainment

6.5

Overall

8.0

Food

6.7

Crew

8.7

Boarding

8.2

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!

Browse thousands of different options on Cheapflights for your next trip

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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 September 11, 2025.

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

    This month, the top selected destinations from New Windsor are Reykjavik Keflavik Intl Airport, Reykjavik, Dublin. 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 Fort Lauderdale (prices may vary depending on the airline and departure time). On average, users have booked flights for $202 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 Nashville Intl ($30), Frontier flights from New Windsor to Orlando ($40), 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?

    February is currently the cheapest month to fly from New Windsor. At this moment in time December 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 Tampa from $104 round trip
    Fly from New Windsor to Myrtle Beach from $113 round trip
    Fly from New Windsor to Charleston from $118 round trip
    Fly from New Windsor to Orlando from $132 round trip

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