$49 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 5/26. 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

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 22% 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.

Flights Deals
Useful Info
Flights Deals

Best Florida Flight Deals from New Windsor

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Orlando
Orlandononstop$119
Fort Lauderdale
Fort Lauderdalenonstop$100
Tampa
Tampa1 stop$173
Fort Myers
Fort Myers3 stops$451
West Palm Beach
West Palm Beach2 stops$343
Jacksonville
Jacksonville2 stops$752
Sarasota
Sarasota2 stops$347
Pensacola
Pensacola1 stop$234
Key West
Key West1 stop$233
Punta Gorda
Punta Gordanonstop$90
Orlando
Orlandononstop$119
Fort Lauderdale
Fort Lauderdalenonstop$100
Tampa
Tampa1 stop$173
Fort Myers
Fort Myers3 stops$451
West Palm Beach
West Palm Beach2 stops$343
Jacksonville
Jacksonville2 stops$752
Sarasota
Sarasota2 stops$347
Pensacola
Pensacola1 stop$234
Key West
Key West1 stop$233
Punta Gorda
Punta Gordanonstop$90

Cheap Flights from New Windsor to Florida

 
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.

Recent round-trip flight deals from New Windsor to Florida

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Windsor to Florida.
Discover the best prices for you by selecting your travel dates on KAYAK.
Allegiant Air Logo
7:18 pm - 10:43 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
3:23 pm - 6:28 pmFLL-SWF
3h 05mnonstop
$100Allegiant Air
Find Deal
Fri, Jun 6 - Mon, Jun 9
Allegiant Air Logo
7:56 pm - 11:21 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
1:41 pm - 4:46 pmFLL-SWF
3h 05mnonstop
$101Allegiant Air
Find Deal
Mon, Aug 11 - Fri, Aug 22
Allegiant Air Logo
11:50 am - 3:15 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
8:00 am - 11:05 amFLL-SWF
3h 05mnonstop
$102Allegiant Air
Find Deal
Mon, May 12 - Mon, May 19
Allegiant Air Logo
11:50 am - 3:15 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
8:00 am - 11:05 amFLL-SWF
3h 05mnonstop
$105Allegiant Air
Find Deal
Mon, May 12 - Fri, May 16
Allegiant Air Logo
7:56 pm - 11:21 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
4:01 pm - 7:06 pmFLL-SWF
3h 05mnonstop
$106Allegiant Air
Find Deal
Fri, Jul 25 - Mon, Aug 4
Allegiant Air Logo
11:55 am - 3:20 pmSWF-FLL
3h 25mnonstop
Allegiant Air Logo
8:00 am - 11:05 amFLL-SWF
3h 05mnonstop
$107Allegiant Air
Find Deal
Mon, May 19 - Fri, May 23
Breeze Airways Logo
7:29 pm - 10:33 pmSWF-MCO
3h 04mnonstop
Breeze Airways Logo
9:00 am - 11:56 amMCO-SWF
2h 56mnonstop
$119Breeze Airways
Find Deal
Sat, Aug 30 - Tue, Sep 2
Breeze Airways Logo
7:52 pm - 10:56 pmSWF-MCO
3h 04mnonstop
Breeze Airways Logo
9:00 am - 11:56 amMCO-SWF
2h 56mnonstop
$122Breeze Airways
Find Deal
Thu, Aug 28 - Tue, Sep 2
Breeze Airways Logo
1:28 pm - 5:55 pmSWF-MCO
4h 27m1 stop
Breeze Airways Logo
8:30 am - 11:26 amMCO-SWF
2h 56mnonstop
$123Breeze Airways
Find Deal
Mon, May 12 - Thu, May 15
 Logo
7:18 pm - 8:24 amSWF-TPA
13h 06m1 stop
 Logo
5:20 am - 6:28 pmTPA-SWF
13h 08m1 stop
Fri, Jun 6 - Mon, Jun 9
Useful Info

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.

What is the cheapest New Windsor to Florida flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from New Windsor to Florida.

The cheapest ticket to Florida from New Windsor found in the last 72 hours was to Orlando, at $75 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 $98.

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 $135 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $268 and $266 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 Wednesday and avoid Mondays if you are looking for the best rates. For your return to Stewart Intl., you’ll find the best rates on Mondays 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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonSeptember
High seasonFebruary
Cheapest flight$49
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from Stewart Intl. to Fort Lauderdale

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.

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

    The cheapest time of day to fly to Florida is generally at night, when round-trip flights cost $180 on average. Morning departures are around 12% 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 $225.

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 $50 one-way - $100 round-trip; Orlando $71 one-way - $187 round-trip; Orlando $59 one-way - $96 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.

Top 5 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 160 reviews
8.3Boarding
8.8Crew
6.7Food
6.6Entertainment
8.2Comfort
Airline reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

8.0 ExcellentAnonymous, Apr 2025PVU - IAD
Read more Breeze Airways reviews

Plane did no snacks and had no wifi or entertainment although the flight was 4 hours long.

My original booking was a nonstop flight. It got changed to a flight with a 6vhour layover that became a 7+ hour lay over. I'll never fly this airline again after this roundtrip is over.

I was surprised at how wonderful it was. The aircraft was clean. The crew was warm and welcoming and as a result the passengers were friendly. One warning the only free thing was water. I kind of liked picking wet hat I was willing to pay for and what I was willing to skip.

The flight wasn’t big on frills, which is fine with me. I flew into Islip MacArthur Airport, which saved me from having to go through LaGuardia to visit friends on Long Island. It was inexpensive and super convenient!

Great experience! This was my first time flying with them and I could not have been happier.

Airplane was newer and very clean, lots of space. Crew was great. There was no food and entertainment but that was expected so not an issue.

I like that the price is right! The airplane is clean and the staff is friendly. We landed safely, so that is always a gold star in my book! Great job!

Purposely delayed the flight by 2 hours and 58 minutes so that they would not have to give me the FAA mandated refund for a delay of 3 hours. Offered flight credit instead. All that is offered on board is water and coffee, everything else costs money. They charge you for carry on and checked bags. Would not fly again.

nice flight. no frills but a 3 hour flight I caught up on my sleep. Stan O

First time flying Breeze, was very impressed. I will use Breeze again.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

Overall was excellent. Will definitely us JetBlue in the future.

Communication with the customer and stay is important. Staff off with a minor inconvenience but it worked out of course. Also this was a very old Mint Class plane. They snuck this one in on us. The updated aircraft are much better.

The flight itself was fine, but the boarding process was extremely frustrating. There is no one scanning boarding passes - passengers just scan themselves and enter the jetway. By the time my husband and I got on the plane and were halfway to our seats they determined there were too many bags on the plane and everything at that point needed to be checked. This created a lot of unnecessary chaos. They should have alerted people before getting on the plane that they would need to start checking bags instead of waiting until people were already on the plane.

The best flight I’ve had in a while. The plane was like 25% capacity, if that. Smoothest boarding and deplaning process I’ve ever experienced. Wish all flights were this smooth.

Traveling with JetBlue from NYC was convenient as accessing JFK airport was straightforward via the LIRR to the AirTrain. Maneuvering through the terminal was hassle-free, which was a pleasant start to the journey. However, the flight experience itself left much to be desired. The seating arrangement was notably uncomfortable; despite securing a window seat, space felt cramped. This was exacerbated by the middle seat passenger encroaching on my area, which made the flight less enjoyable. Additionally, while the in-flight entertainment system initially seemed like a reprieve, the sound outlet on my seat was inoperable. This issue turned what could have been a manageable three-hour flight into a rather tedious ordeal, as I was unable to use the entertainment system effectively. While JetBlue provided a smooth process in terms of airport logistics, the on-board experience highlighted areas in need of improvement, particularly in terms of comfort and entertainment system maintenance.

The flight crew that we had in our section may have been tired or something. I asked the flight attendant about my son’s screen not working and she spoke down to me like I was stupid. He still had no working screen throughout his flight. The other members had no personality and seemed like they were annoyed when you asked them for something. Definitely took a hit for simple things on my JB experience.

Over 2 hour delay for a 50-minute flight is unacceptable, especially in normal weather. Very poor communication via app

In-flight staff was very helpful and excellent. However, the flight was delayed by 90 minutes. Also the boarding process should be expedited in case of delayed flights. This will help the passengers trying to make international connections.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Posted a 20minute delay but didn’t delay at all. Caused boarding issues and confusion. Also, didn’t release baggage. Took over an hour and 20 minutes to get luggage.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The flight attendant spilled ice all down my leg and all over my suede boots and didn’t even apologize or anything. They just gave me a look like “what?!” Incredibly rude and dismissive. I saw them roll their eyes at other guests and even once yell at a lady with a baby.

It’s what we expected from Spirit..reasonable cost, good for a 2-3 hour flight. Disappointed that we had a 2 hour delay in departure from DFW for a maintenance issue, but the pilot handled it well once we were outbound on a different Airbus.

My experience was okay. The flight did not offer even water without a fee. Also had to pay extra for my carry on, as I was told I had to check my bag, even though it said I had the option to carry on a bag when booking. This costed me an extra $100. Would likely not fly with Spirit again.

The flight was rescheduled several times without a reason for the schedule changes. I had to be in New Orleans at a certain time and it was just easier to drive at a certain point. I don’t know if the flight ever left. This is my first experience with Spirit Airlines and is also the last.

In a word, it was horrible. The flight crew timed out and this, apparently was not accounted for by management. This meant that our 10:15 departure turned into a 1:30am departure the next DAY!!! And some brainchild decided to email us 12$ food vouchers set to expire the 9th, but they sent them after EVERY VENDOR WAS CLOSED in the Miami airport and obviously none would be open in New Orleans. I found this to be another sterling example of, at best, shitty management…at worst an absolute lack of empathy for your customers. Triplt Pro: Check-in may be avail for NK222 dep MIA 4/8/2025 10:16pm. Conf#RGSUMI. https://tripit.com/t/. e106fd644e0a; Today 6:16 PM TripIt Pro: NK222 ON TIME. MIA dep 10:16pm term C, gate F5. MSY arr 11:38pm. Today 8:59 PM Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 2:18am. Alternate flights: https:// www.tripit.com/t/b2903869f438 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/834d176c630b Tript Pro: NK222 DELAYED. MIA dep 1:00am term C, gate F5. MSY arr 1:48am. Alternate flights: https:/// www.tripit.com/t/0441e41a9dd3 Triplt Pro: NK222 PULLED IN. MIA dep 12:30am term C, gate F5. MSY arr 1:48am. Alternate flights: https:// www.tripit.com/t/92ac2157ef54 The sender is not in your contact

Perfect for the money paid. Flight from Indianapolis to Fort Lauderdale. Very courteous airport staff and crew. The boarding process went very smooth. Indianapolis was in the middle of several sever storms, delaying boarding and they found a window between the storms, asked everyone for a quick boarding and we departed before we would be held longer by the next storm front. A little rough air 20 min or so after take off, however I’ll take that to being grounded the whole night. Seats kind of small, kind of hard, but very doable for the 2.5 hrs flight. Snacks and drinks available for purchase. We didn’t, as it was a late night flight. One of the checked luggage came wet in Florida and clothes inside got wet from the water that infiltrated through the zipper, I’m assuming it was in the rain in Indianapolis, I cannot blame Spirit as I think the baggage handlers are hired by the airport. I’ll be more careful next time, as I have suitcases that are more water proof and maybe I should only purchase that kind.

Terrible! They kept postponing and finally canceled our flight. They canceled so late. We had no other options but to drive to a different city and try to find a new flight to get onto our cruise. We still aren’t there yet and might not make it.

The flight was on time. The seats are very narrow.

No leg room AT all extremely uncomfortable flight water even cost 5 dollars

This was my first experience with Spirit. The flight was originally delayed because of mechanical problems. There was a major storm moving through our area later in the day. Spirit kept changing the gate and taking the plane for other flights. They did this 6 times until we left 7 hours later, right at the worse time. I am sure it is because they originally delayed the flight through their fault. They would have had to pay for everybody's hotel and later flight. It was a money decision. The pilot did an exceptional job flying and landing the plane in horrific weather. It was one of the roughest and shakiest landings that I have ever done in my extensive flying experience. I just can never go through this discount BS again. Spirit gave us a $30 voucher each for next travel and a $12 meal voucher... but that's nothing compared to sitting in an airport for 7 hours.

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

I chose the seats when booked the flight and paid for them. However after checking in I found we were assigned different seats!

It was a no frills flight. Would have liked to be able to charge my device

Seats were extremely uncomfortable and it was very hot on the plane.

Since they are a budget airline, I wasn’t expecting too much but they did some things well. They were on time, the plane was clean, boarding was fairly straightforward and the staff was cheerful and friendly. The only downside was comfort. The seats were fairly hard and after a 2 hour flight your rear end is not feeling so great. Maybe a little more cushion in the seats, Frontier!

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

Boarding was organized and flight was on time. Overall very satisfied with my flight.

The boarding gate was in Terminal D, but the Frontier counter was in Terminal E. So I had to move back and forth between terminals to check in my luggage. This was the worst experience that I had in terms of flights.

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.