What is the cheapest airline that flies from New Windsor Stewart to Florida Keys?

Breeze Airways and Allegiant Air are the most popular carriers operating from New Windsor Stewart to Florida Keys

What airlines fly to Florida Keys?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Florida Keys from New Windsor according to our data. United Airlines is the first choice among our users, with 63% of people opting to fly with this airline when traveling to Florida Keys. Keep in mind that there are 3 different airlines that fly to Florida Keys on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from New Windsor Stewart Airport to Florida Keys?

Prices for flights from New Windsor Stewart Airport to Florida Keys are refreshed on a daily basis.

How many operators does momondo search for flights from New Windsor Stewart Airport to Florida Keys?

There are 2 operators available for flights from New Windsor Stewart Airport to Florida Keys as of August 2026.

How old do you have to be to fly from New Windsor Stewart Airport to Florida Keys?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New Windsor Stewart Airport to Florida Keys.

What documentation or ID do you need to fly to Florida Keys?

The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$97 Cheap Flights from New Windsor to Florida Keys in 2026

Find the cheapest flights from New Windsor to Florida Keys

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

12:39 pm - 9:24 pmSWF New Windsor Stewart-MIA Miami

8h 45m1 stop Raleigh-Durham

9:00 am - 11:39 amMIA Miami-SWF New Windsor Stewart

26h 39m1 stop Raleigh-Durham

$207Multiple Airlines

Sat, Oct 17 - Fri, Nov 6

12:39 pm - 9:24 pmSWF New Windsor Stewart-MIA Miami

8h 45m1 stop Raleigh-Durham

9:00 am - 11:39 amMIA Miami-SWF New Windsor Stewart

26h 39m1 stop Raleigh-Durham

$214Multiple Airlines

Sat, Oct 17 - Fri, Nov 6

12:39 pm - 9:24 pmSWF New Windsor Stewart-MIA Miami

8h 45m1 stop Raleigh-Durham

9:00 am - 11:39 amMIA Miami-SWF New Windsor Stewart

26h 39m1 stop Raleigh-Durham

$217Multiple Airlines

Sat, Oct 17 - Fri, Nov 6

12:39 pm - 2:19 pmSWF New Windsor Stewart-MIA Miami

25h 40m1 stop Raleigh-Durham

9:00 am - 11:39 amMIA Miami-SWF New Windsor Stewart

26h 39m1 stop Raleigh-Durham

$223Multiple Airlines

Wed, Oct 28 - Fri, Nov 6

12:39 pm - 3:19 pmSWF New Windsor Stewart-MIA Miami

26h 40m1 stop Raleigh-Durham

9:00 am - 11:39 amMIA Miami-SWF New Windsor Stewart

26h 39m1 stop Raleigh-Durham

$229Multiple Airlines

Sat, Oct 31 - Fri, Nov 6

12:39 pm - 9:24 pmSWF New Windsor Stewart-MIA Miami

8h 45m1 stop Raleigh-Durham

7:17 pm - 12:08 pmMIA Miami-SWF New Windsor Stewart

40h 51m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$235Multiple Airlines

Sat, Oct 24 - Fri, Oct 30

12:39 pm - 11:21 amSWF New Windsor Stewart-EYW Key West

22h 42m2 stops Raleigh-Durham Tampa

10:04 am - 10:23 amEYW Key West-SWF New Windsor Stewart

24h 19m1 stop Tampa

$236Multiple Airlines

Sat, Sep 12 - Sat, Sep 19

12:39 pm - 11:21 amSWF New Windsor Stewart-EYW Key West

22h 42m2 stops Raleigh-Durham Tampa

10:04 am - 10:23 amEYW Key West-SWF New Windsor Stewart

24h 19m1 stop Tampa

$238Multiple Airlines

Sat, Sep 12 - Sat, Sep 19

12:39 pm - 9:24 pmSWF New Windsor Stewart-MIA Miami

8h 45m1 stop Raleigh-Durham

5:05 am - 11:03 amMIA Miami-SWF New Windsor Stewart

29h 58m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale

$241Multiple Airlines

Sat, Oct 10 - Sat, Oct 17

12:39 pm - 11:21 amSWF New Windsor Stewart-EYW Key West

22h 42m2 stops Raleigh-Durham Tampa

6:11 pm - 10:16 amEYW Key West-SWF New Windsor Stewart

16h 05m1 stop Orlando Sanford Intl

$247Multiple Airlines

Sat, Sep 12 - Thu, Sep 17

Cheap last minute flights

Enter your travel dates to find the best prices.

1:44 pm - 7:13 pmSWF New Windsor Stewart-EYW Key West

53h 29m2 stops Myrtle Beach Intl Tampa

6:21 pm - 10:06 amEYW Key West-SWF New Windsor Stewart

15h 45m1 stop Orlando Sanford Intl

$471Multiple Airlines

Fri, Aug 21 - Thu, Aug 27

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

6:21 pm - 10:06 amEYW Key West-SWF New Windsor Stewart

15h 45m1 stop Orlando Sanford Intl

$575Allegiant Air

Thu, Aug 20 - Thu, Aug 27

1:44 pm - 10:24 amSWF New Windsor Stewart-EYW Key West

44h 40m2 stops Myrtle Beach Intl Tampa

12:54 pm - 10:27 amEYW Key West-SWF New Windsor Stewart

21h 33m1 stop Tampa St. Petersburg

$587Multiple Airlines

Fri, Aug 21 - Wed, Aug 26

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

11:46 am - 6:41 pmEYW Key West-SWF New Windsor Stewart

30h 55m2 stops Tampa Fort Lauderdale

$609Multiple Airlines

Thu, Aug 20 - Wed, Aug 26

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

1:14 pm - 11:25 amEYW Key West-SWF New Windsor Stewart

22h 11m2 stops Tampa Raleigh-Durham

$625Multiple Airlines

Thu, Aug 20 - Tue, Aug 25

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

3:51 pm - 4:49 pmEYW Key West-SWF New Windsor Stewart

24h 58m1 stop Orlando Sanford Intl

$660Allegiant Air

Thu, Aug 20 - Sun, Aug 23

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

12:05 pm - 11:37 amEYW Key West-SWF New Windsor Stewart

23h 32m2 stops Orlando Charleston

$662Multiple Airlines

Thu, Aug 20 - Thu, Aug 27

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

11:46 am - 10:27 amEYW Key West-SWF New Windsor Stewart

22h 41m1 stop Tampa

$664Multiple Airlines

Thu, Aug 20 - Wed, Aug 26

11:17 am - 10:09 amSWF New Windsor Stewart-EYW Key West

22h 52m1 stop Tampa St. Petersburg

12:54 pm - 10:27 amEYW Key West-SWF New Windsor Stewart

21h 33m1 stop Tampa St. Petersburg

$674Allegiant Air

Thu, Aug 20 - Wed, Aug 26

12:05 pm - 1:32 pmSWF New Windsor Stewart-MIA Miami

25h 27m2 stops Raleigh-Durham Atlanta Hartsfield-Jackson

3:30 pm - 11:25 amMIA Miami-SWF New Windsor Stewart

19h 55m1 stop Raleigh-Durham

$675Multiple Airlines

Wed, Aug 19 - Fri, Aug 21

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Breeze Airways flights from New Windsor to Florida Keys

Our best Breeze Airways deals on New Windsor to Florida Keys flight tickets

Breeze Airways

Sep 11

SWF12:16 pmNew Windsor Stewart

21h 08m

2 stops

EYW9:24 amKey West

Sep 18

EYW11:59 amKey West

23h 40m

1 stop

SWF11:39 amNew Windsor Stewart

$244

Breeze Airways

Sep 13

SWF10:56 amNew Windsor Stewart

23h 23m

1 stop

EYW10:19 amKey West

Sep 18

EYW11:59 amKey West

23h 40m

1 stop

SWF11:39 amNew Windsor Stewart

$253

Breeze Airways

Sep 11

SWF12:16 pmNew Windsor Stewart

21h 08m

2 stops

EYW9:24 amKey West

Sep 18

EYW11:59 amKey West

23h 40m

1 stop

SWF11:39 amNew Windsor Stewart

$263

Allegiant Air flights from New Windsor to Florida Keys

Our best Allegiant Air deals on New Windsor to Florida Keys flight tickets

Allegiant Air

Sep 3

SWF11:13 amNew Windsor Stewart

5h 06m

1 stop

EYW4:19 pmKey West

Sep 10

EYW6:11 pmKey West

16h 05m

1 stop

SWF10:16 amNew Windsor Stewart

$280

Allegiant Air

Nov 8

SWF5:37 pmNew Windsor Stewart

20h 24m

1 stop

EYW2:01 pmKey West

Nov 12

EYW8:54 pmKey West

19h 46m

1 stop

SWF4:40 pmNew Windsor Stewart

$320

Allegiant Air

Aug 20

SWF11:17 amNew Windsor Stewart

22h 52m

1 stop

EYW10:09 amKey West

Aug 27

EYW6:21 pmKey West

15h 45m

1 stop

SWF10:06 amNew Windsor Stewart

$575

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/17

12:39 pm-9:24 pm

1 stop8h 45m

Miami

Fri 11/6

9:00 am-11:39 am

1 stop26h 39m

$207

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/17

12:39 pm-9:24 pm

1 stop8h 45m

Miami

Fri 11/6

9:00 am-11:39 am

1 stop26h 39m

$214

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/17

12:39 pm-9:24 pm

1 stop8h 45m

Miami

Fri 11/6

9:00 am-11:39 am

1 stop26h 39m

$217

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Wed 10/28

12:39 pm-2:19 pm

1 stop25h 40m

Miami

Fri 11/6

9:00 am-11:39 am

1 stop26h 39m

$223

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/31

12:39 pm-3:19 pm

1 stop26h 40m

Miami

Fri 11/6

9:00 am-11:39 am

1 stop26h 39m

$229

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/24

12:39 pm-9:24 pm

1 stop8h 45m

Miami

Fri 10/30

7:17 pm-12:08 pm

2 stops40h 51m

$235

New WindsorKey West

SWF New Windsor Stewart - EYW Key West

SWFEYW

New Windsor Stewart

Sat 9/12

12:39 pm-11:21 am

2 stops22h 42m

Key West

Sat 9/19

10:04 am-10:23 am

1 stop24h 19m

$236

New WindsorKey West

SWF New Windsor Stewart - EYW Key West

SWFEYW

New Windsor Stewart

Sat 9/12

12:39 pm-11:21 am

2 stops22h 42m

Key West

Sat 9/19

10:04 am-10:23 am

1 stop24h 19m

$238

New WindsorMiami

SWF New Windsor Stewart - MIA Miami

SWFMIA

New Windsor Stewart

Sat 10/10

12:39 pm-9:24 pm

1 stop8h 45m

Miami

Sat 10/17

5:05 am-11:03 am

2 stops29h 58m

$241

New WindsorKey West

SWF New Windsor Stewart - EYW Key West

SWFEYW

New Windsor Stewart

Sat 9/12

12:39 pm-11:21 am

2 stops22h 42m

Key West

Thu 9/17

6:11 pm-10:16 am

1 stop16h 05m

$247

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from New Windsor to Florida Keys

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the cheapest month to fly to Florida Keys?

The month of January is another great option to travel to Florida Keys, with average flight prices from New Windsor averaging around $60.

Can stopping save me money on New Windsor to Florida Keys flights?

No. A direct flight is the cheapest option for a flight between New Windsor to Florida Keys.

Cheap New Windsor to Florida Keys flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Florida Keys

Fastest flight time	5h 20m
Direct flights	None

The fastest flight from New Windsor to Florida Keys takes 5h 20m

There are no direct flights from New Windsor to Florida Keys. There are no popular flight routes from New Windsor to Florida Keys.

Search flight deals

Frequently asked questions about flying from New Windsor to Florida Keys

When did momondo last update prices for flights from New Windsor Stewart Airport to Florida Keys?
Prices for flights from New Windsor Stewart Airport to Florida Keys are refreshed on a daily basis.
How many operators does momondo search for flights from New Windsor Stewart Airport to Florida Keys?
There are 2 operators available for flights from New Windsor Stewart Airport to Florida Keys as of August 2026.
How old do you have to be to fly from New Windsor Stewart Airport to Florida Keys?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from New Windsor Stewart Airport to Florida Keys.
What documentation or ID do you need to fly to Florida Keys?
The necessary travel and health documents for your Florida Keys trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from New Windsor to Florida Keys?
momondo data reveals that the most frequently booked plane model on the route from New Windsor to Florida Keys is Airbus A320-100/200, representing 21.13% of all bookings. The subsequent popular models are Airbus A321-100/200 at 12.54%, Boeing 737 MAX 8 at 11.92%, and Airbus A220-300 at 11.83%.

Why use momondo?

Why should I use momondo to find a flight deal from New Windsor to Florida Keys?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Florida Keys. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from New Windsor to Florida Keys with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for New Windsor to Florida Keys flights to just show those with flexible booking policies.

How can momondo help me find flights from New Windsor to Florida Keys?

Once you have performed a search for New Windsor to Florida Keys flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from New Windsor to Florida Keys right now. Can momondo alert me if prices change?

Price alerts on flights to Florida Keys from New Windsor are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.