$43 Find Cheap Flights from New Windsor to Florida

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Windsor to Florida departing on 5/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Florida

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Florida, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Windsor to Florida, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from New Windsor to Florida

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Orlando
Orlando1 stop$131
Miami
Miami2 stops$279
Fort Lauderdale
Fort Lauderdalenonstop$87
Tampa
Tampa1 stop$129
Fort Myers
Fort Myers1 stop$197
West Palm Beach
West Palm Beach1 stop$248
Jacksonville
Jacksonville1 stop$295
Sarasota
Sarasota2 stops$1,018
Pensacola
Pensacola2 stops$290
Key West
Key West1 stop$201
Punta Gorda
Punta Gordanonstop$144
Orlando
Orlando1 stop$131
Miami
Miami2 stops$279
Fort Lauderdale
Fort Lauderdalenonstop$87
Tampa
Tampa1 stop$129
Fort Myers
Fort Myers1 stop$197
West Palm Beach
West Palm Beach1 stop$248
Jacksonville
Jacksonville1 stop$295
Sarasota
Sarasota2 stops$1,018
Pensacola
Pensacola2 stops$290
Key West
Key West1 stop$201
Punta Gorda
Punta Gordanonstop$144

Book Cheap New Windsor to Florida Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Windsor to Florida that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Windsor to Florida

Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$87Allegiant Air
Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$98Allegiant Air
Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$102Allegiant Air
Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$103Allegiant Air
Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$107Allegiant Air
Sun, Apr 26 - Thu, Apr 30
Allegiant Air Logo
11:45 am - 2:52 pm
SWF
-
FLL
3h 07mnonstop
Allegiant Air Logo
7:40 am - 10:55 am
FLL
-
SWF
3h 15mnonstop
$109Allegiant Air
Sat, May 30 - Sat, Jun 6
Breeze Airways Logo
12:05 pm - 4:26 pm
SWF
-
TPA
4h 21m
1 stop
Breeze Airways Logo
7:00 am - 11:25 am
TPA
-
SWF
4h 25m
1 stop
$129Breeze Airways
Wed, Jun 3 - Sat, Jun 6
Breeze Airways Logo
12:05 pm - 4:26 pm
SWF
-
TPA
4h 21m
1 stop
Breeze Airways Logo
7:00 am - 11:25 am
TPA
-
SWF
4h 25m
1 stop
$130Breeze Airways
Wed, Jun 3 - Wed, Jun 10
Breeze Airways Logo
12:05 pm - 5:02 pm
SWF
-
MCO
4h 57m
1 stop
Breeze Airways Logo
7:00 am - 11:25 am
MCO
-
SWF
4h 25m
1 stop
$131Breeze Airways
Sun, May 3 - Thu, May 7
Multiple Airlines Logo
11:48 am - 12:26 pm
SWF
-
EYW
24h 38m
1 stop
Multiple Airlines Logo
1:57 pm - 10:55 am
EYW
-
SWF
20h 58m
1 stop
$201Multiple Airlines
Booking Insights

KAYAK's insights & trends for New Windsor to Florida flights

Get data-powered insights and trends into flights from New Windsor to Florida to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from New Windsor to Florida?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from New Windsor to Florida departing in June.

What is the cheapest New Windsor to Florida flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida from New Windsor found in the last 72 hours was to Orlando, at $76 round-trip. The most popular route is from New Windsor (SWF) to Fort Lauderdale (FLL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $87.

What is the cheapest time of day to fly to Florida?

The average price for all round-trip flights from New Windsor to Florida depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida is generally at night, when round-trip flights cost $190 on average. Morning departures are around 6% more expensive than evening flights, on average. The most expensive time of day to fly to Florida is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $342.

Can I save money by flying with a layover from New Windsor to Florida?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $194, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New Windsor to Florida, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New Windsor to Florida is January, when tickets cost $155 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $357 and $313 respectively.

What’s the cheapest day of the week to fly from Stewart Intl. to Florida?

The average price of all round-trip flights from New Windsor to Florida clicked on KAYAK for each day over the last 12 months.

When flying from Stewart Intl. to Florida, you should consider leaving on a Saturday and avoid Fridays if you are looking for the best rates. For your return to Stewart Intl., you’ll find the best rates on Fridays and the most expensive ones on Sundays.

How far in advance should I book a flight from New Windsor to Florida?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New Windsor to Florida, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New Windsor to Florida, you should book around 5 weeks before departure, which saves you about 37% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$44
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 30% increase in price.
Flight from Stewart Intl. to Orlando Airport

FAQs - booking Florida flights

  • Do I need a visa to travel from Toronto to Hawaii?

    In general, Canadian citizens do not require a visa to go to the United States. Canadian citizens are generally allowed to stay in the country for up to six months without having a visa or a residency permit. They must have a valid passport that does not expire before their return to Canada.

  • What airport in Hawaii is closest to Waimea Canyon State Park?

    If you plan on visiting Waimea Canyon State Park on the island of Kauai, you will want to fly to Lihue Airport (LIH), as this is the airport that is closest to this area. Once you land at Lihue Airport, Waimea Canyon State Park is just under a 1-hour drive away.

  • Are there any nonstop flights from Toronto to Hawaii?

    As it is such a long distance from Toronto and Hawaii, it is important to keep in mind that there are no direct flights between these locations. Instead, you should plan on having either one or two layovers before reaching your destination. These may take place in cities such as Calgary or Winnipeg.

  • What are some sustainable airlines that service flights from Toronto to Hawaii?

    Air Canada has made substantial efforts to reduce its carbon footprint. For example, the company has committed to reaching net zero greenhouse gas emissions by 2050. It also has invested millions of dollars in upgrading its fleet to newer planes that emit fewer emissions and use less fuel. 

  • How does KAYAK find such low prices on flights from Stewart Intl. to Florida?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Stewart Intl. to Florida.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Stewart Intl. to Florida?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Stewart Intl. to Florida is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Stewart Intl. to Florida?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Stewart Intl. to Florida with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Stewart Intl. to Florida?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Stewart Intl. to Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Florida

  • Looking for a cheap flight? 25% of our users found tickets from Stewart Intl. to the following destinations at these prices or less: Fort Lauderdale $83 one-way - $116 round-trip; Tampa $114 one-way - $172 round-trip; Orlando $70 one-way - $124 round-trip
  • If you are flying from Toronto to Hawaii to surf, you will want to try to go to Oahu, as the North Shore part of the island is known for having some of the best surfing in the state. There are several airlines that offer flights to Daniel K. Inouye International Airport (HNL) from Toronto, including Air Canada and WestJet.
  • Flights from Toronto to Hawaii tend to be rather long journeys, so you may want to consider upgrading yourself to either Premium Economy or Business Class to have some additional comfort and legroom. After you have made your reservation, most companies will give you the option of upgrading at a discounted rate, such as WestJet.
  • Those who intend on visiting several Hawaiian Islands may first want to fly into Daniel K. Inouye International Airport in Honolulu. This is the largest airport in the state and offers regional flights to all the other airports in Hawaii, making it a convenient home base for your travels.
  • To save some money during your trip from Toronto to Hawaii, consider flying in Basic Economy, or a class that is equivalent. Both WestJet and Air Canada offer a Basic Economy class that you can choose from for this route.
  • When flying from Toronto to Hawaii, you will find that it is typically most convenient to fly out of Toronto Pearson International Airport (YYZ). YYZ is the largest airport in Canada, and it offers the most daily international flights out of all the airports in the greater Toronto region.

Reviews of the top 4 airlines serving from New Windsor to Florida

 
See real verified KAYAK customer reviews for airlines flying from New Windsor to Florida. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from New Windsor to Florida? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.1
Breeze AirwaysOverall score based on 280 reviews
8.2Comfort
6.6Entertainment
8.7Crew
6.6Food
8.3Boarding
Airline reviews

I normally have very good experiences with Breeze. The crew is great, pricing is excellent, and the planes are new and usually clean. This time in Huntsville we were delayed, which I understand can happen, however we were moved from one gate to the opposite side of the terminal and then back again... There was a lot of confusion. Also, my seat had a lot of food crumbs still on the floor where I had to stow my bookbag, so that was a bit disappointing. Other than that, all was good. Crew was great as usual!

8.0 ExcellentBrian, Apr 2026
HSV - TPA
Read more Breeze Airways reviews

I normally have very good experiences with Breeze. The crew is great, pricing is excellent, and the planes are new and usually clean. This time in Huntsville we were delayed, which I understand can happen, however we were moved from one gate to the opposite side of the terminal and then back again... There was a lot of confusion. Also, my seat had a lot of food crumbs still on the floor where I had to stow my bookbag, so that was a bit disappointing. Other than that, all was good. Crew was great as usual!

Our flight was delayed 7 hours. Due to a change in equipment we were downgraded from "Nicest" to "Nicer," even having to pay for a soft drink. Disappointing. To Breeze's credit that issued a $100 flight credit. A refund would have been more appreciated.

Lost my luggage and terrible experience with customer service trying to track it down

10 hour delay with minimal updates. Couldn’t leave terminal and then ended up on redeye with a dirty broken plane. It is literally impossible to reach customer service via gate agent, app, phone, text or email.

I thought that I had pre-purchased carry-on luggage and was surprised when I tried to check in that I did not have it.

Flight departure was 90 min delayed, and the boarding experience was confused, stressful, and generally poor. Additionally, the wifi on the plane was malfunctioning for all but the final 15 min of the flight into ILM.

Great experience and In love flying in and out of Provo airport

You get what you pay for. It’s like a bus but flying. No frills, no snacks. Leg room was fine, boarding was good.

Overall good. Plenty of legroom and fairly comfortable seats. No issues with capacity and the overhead been even though most people brought several carry-ons on. I don’t think Breeze really enforces the pay for a carry-on rule.

Surprised at how much I enjoyed Breeze. Paid for the Nicer upgrade which made it closer in price to a flag ship carrier but with more comfortable seats and much more leg room. Crew was polite and since we brought our food no loss there. Would make the point that the ‘have to pay for a carry-on is BS’. Most people did not and had several. Still was plenty of room in the overheads.

just had water and there was plenty of leg & seat room. But then i don't weight 220#s!!

Not totally their fault- screaming kids that had zero parent intervention.

It was cold on the flight. The crew was very pleasant. I didn't order any food. We were delayed due to Captain waiting on maintenance log. He kept us informed though. The flight itself was smooth. I would definitely fly with Allegiant again!

I had a fantastic experience with Allegiant. I had wheelchair assistance and they helped me find my luggage and brought me to my car. Even loaded my luggage. Wonderful service!! Thank you Allegiant!

Superb. Staff great. Great flight. As with other airlines, seating too tight and restrictive.

There is not one likable thing about this airline. It’s starts with the deceptive pricing and continues through the whole flight. The worst staff I’ve ever experienced way over priced bags absolutely no food or drink (unacceptable and you should be embarrassed) the seats are cramped and uncomfortable there is no entertainment there is nothing about this trash airline that constitutes any amount of money. It’s worse than spirit and way more expensive it is disgraceful. Do not travel with Allegiant I repeat do not bother no matter what they say the price is it is never ever going to be the right choice I’m mind blown at how awful the entire experience was I’m embarrassed that I chose so poorly I cannot reiterate enough how beyond horrible this company and its staff are, not one person on this flight or at the airport is qualified to sweep up trash on a city sidewalk they should certainly never be given any job that requires a brain or manners or communication with human beings, what a disgrace to the human race. Your criminal chiselers and should be put out to pasture

Great flight. Friendly staff. Free snacks and drinks would be nice. I would love fewer taxes and fees added on.

My 90 year old father flew with me. He needed wheel chair assistance and is nearly deaf. The staff was amazing with him.

It was fine. Nobody was outstandingly friendly but no one was rude and everything was smooth . The captain thanked us for flying but no one greeted me as I walked on the plane or as I exited which is the least they could do lol

Clean, friendly, roomy. But check-in from the phone link was terrible. Repeated attempts wouldn’t save at the final step. Just kept spinning! It was very frustrating. Finally, I used the app (vs website link) to check-in which worked very smoothly on the first attempt.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

The repeated flight delays—this time nearly three hours without any weather-related cause—are unacceptable. Yet, passengers are penalized heavily even for being a minute late. It is unreasonable that there is no compensation for such significant delays, nor even basic provisions like water during the wait or in flight. This imbalance in accountability is deeply frustrating and needs to be addressed.

Always Good ,… Spirit customers are high class Delta customers are self proclaimed elites and American crews you can hear them complain about everything (they’re loud)

They cancelled my flight with no reason affecting my travel plans and delaying it 24 hours.

Everything was horrible. They delayed my flight so I missed my connection flight and I lost my bags. I had to go to the same workers multiple times asking the same questions because everyone kept giving me different answers. One person closed down customer service because he wanted to go on lunch so there was like 30 people just waiting for hours because no one would relieve him.

Landing was technically perfect. What I didn't like is the pricey internet. Both flights with excellent crews. I'm 6 feet 210 pounds and could easily fit in the chair.

First flight in along time with spirit! I’m honored to say this flight was excellent 😊

Every connection was late but that meant I was not running from one to the next so that was a good thing. No one wants to miss a connection

We had to take a bus to the plane with a old woman and carry on bags, and at landing at the airport we have to wait one hour seating on the plane waiting for a gate. We came back from Australia Bussines class Quantas 16 hours traveling, then wait in Dallas 7 hours for connection...honestly waiting 1 hour more at the plane was the worst part.

Flight delayed twice (not Spirit fault) No food served* No entertainment * *in response to my choices in the rating. None was provided so couldn’t rate properly

Everything you need to know for your flight from New Windsor to Florida

Information on your arrival and departure airports