$46 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 11/17. 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 23% 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
Orlandononstop$122
Miami
Miami2 stops$249
Fort Lauderdale
Fort Lauderdalenonstop$92
Tampa
Tampa1 stop$181
Fort Myers
Fort Myers1 stop$403
West Palm Beach
West Palm Beach1 stop$277
Jacksonville
Jacksonville3 stops$619
Sarasota
Sarasota2 stops$403
Pensacola
Pensacola1 stop$221
Key West
Key West1 stop$230
Valparaiso
Valparaiso2 stops$482
Punta Gorda
Punta Gordanonstop$164
Orlando
Orlandononstop$122
Miami
Miami2 stops$249
Fort Lauderdale
Fort Lauderdalenonstop$92
Tampa
Tampa1 stop$181
Fort Myers
Fort Myers1 stop$403
West Palm Beach
West Palm Beach1 stop$277
Jacksonville
Jacksonville3 stops$619
Sarasota
Sarasota2 stops$403
Pensacola
Pensacola1 stop$221
Key West
Key West1 stop$230
Valparaiso
Valparaiso2 stops$482
Punta Gorda
Punta Gordanonstop$164

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

Fri, Dec 5 - Mon, Dec 8
Allegiant Air Logo
12:27 pm - 3:40 pmSWF-FLL
3h 13mnonstop
Allegiant Air Logo
8:30 am - 11:37 amFLL-SWF
3h 07mnonstop
$92Allegiant Air
Find Deal
Mon, Nov 17 - Fri, Nov 21
Allegiant Air Logo
12:01 pm - 3:32 pmSWF-FLL
3h 31mnonstop
Allegiant Air Logo
7:15 am - 10:22 amFLL-SWF
3h 07mnonstop
$94Allegiant Air
Find Deal
Fri, Dec 5 - Mon, Dec 8
Allegiant Air Logo
12:27 pm - 3:40 pmSWF-FLL
3h 13mnonstop
Allegiant Air Logo
8:30 am - 11:37 amFLL-SWF
3h 07mnonstop
$96Allegiant Air
Find Deal
Mon, Jan 19 - Fri, Jan 23
Allegiant Air Logo
11:09 am - 2:52 pmSWF-FLL
3h 43mnonstop
Allegiant Air Logo
7:15 am - 10:19 amFLL-SWF
3h 04mnonstop
$97Allegiant Air
Find Deal
Fri, Nov 14 - Fri, Nov 21
Allegiant Air Logo
11:01 am - 2:32 pmSWF-FLL
3h 31mnonstop
Allegiant Air Logo
7:15 am - 10:22 amFLL-SWF
3h 07mnonstop
$99Allegiant Air
Find Deal
Mon, Jan 5 - Fri, Jan 9
Allegiant Air Logo
11:37 am - 2:50 pmSWF-FLL
3h 13mnonstop
Allegiant Air Logo
7:15 am - 10:19 amFLL-SWF
3h 04mnonstop
$100Allegiant Air
Find Deal
Sun, Jan 11 - Thu, Jan 15
Breeze Airways Logo
11:48 am - 3:07 pmSWF-MCO
3h 19mnonstop
Breeze Airways Logo
8:10 am - 11:08 amMCO-SWF
2h 58mnonstop
$127Breeze Airways
Find Deal
Mon, Jan 19 - Thu, Jan 22
Breeze Airways Logo
12:11 pm - 4:49 pmSWF-MCO
4h 38m1 stop
Breeze Airways Logo
8:10 am - 11:08 amMCO-SWF
2h 58mnonstop
$129Breeze Airways
Find Deal
Fri, Jan 9 - Sun, Jan 11
Breeze Airways Logo
12:11 pm - 4:49 pmSWF-MCO
4h 38m1 stop
Breeze Airways Logo
8:10 am - 11:08 amMCO-SWF
2h 58mnonstop
$130Breeze Airways
Find Deal
Mon, Jan 19 - Fri, Jan 23
Multiple Airlines Logo
11:09 am - 2:52 pmSWF-FLL
3h 43mnonstop
Multiple Airlines Logo
9:02 am - 6:43 pmFLL-SWF
9h 41m1 stop
$152Multiple Airlines
Find Deal
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.

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 Fort Lauderdale, at $94 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 $94.

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 $219, 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 May, when tickets cost $136 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $292 and $263 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 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 3 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$46
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 11% 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 in the evening, when round-trip flights cost $173 on average. Morning departures are around 8% 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 $272.

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 $48 one-way - $100 round-trip; Punta Gorda $114 one-way - $176 round-trip; Orlando $110 one-way - $162 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 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 220 reviews
8.1Comfort
6.6Entertainment
6.7Food
8.3Boarding
8.7Crew
Airline reviews

Ridiculous to have to pay for carry on and to pick seats

6.0 GoodAnonymous, Oct 2025BDL - MYR
Read more Breeze Airways reviews

Ridiculous to have to pay for carry on and to pick seats

We did have a delay but nothing that affected our schedule to terribly. Breeze is the best budget airline that we have found for the eastern seaboard. Price is good. Baggage rates aren't terrible. I suggest checking a bag which gets you more bang for your buck. They fly into smaller airports which is so much easier than trying to get through Logan or JFK. Overall good trip.

First time flying Breeze everything went smoothly. Left early and arrived early to our destination. Definitely will be flying again with them!😊

Great! Only problem is we can’t use the northbound flight on this route as it arrives much too late and is not non-stop.

Given some type of snack. Had staff that hated their job and life in general. Have regular overhead bins. The bags have to go sideways and even then, they barely fit. The seats in the front - what would be considered business class were nice. Nothing extra but nice for a short flight. But the regular seats were so close I have no idea how people even fit it them.

Our gate was changed twice, but since they were super close it wasn't an issue. We were delayed 90 mins or so, which wasn't great, but sometimes that's just what happens. Communication was the issue. We weren't kept informed about delays--with more information I would have gotten a real meal, taken a "bio break" and purchased a new book. Because another. flight was being updated more frequently about their delays, I thought ours would be shorter and stayed close by. It left me feeling more frustrated than was necessary.

Your feedback should include a "not applicable" button. There was no food, nor entertainment on our flight. Also, a snack on a short flight will be nice to have

Boarding at BDL gate 24 was confused, but balanced out by friendly, responsive gate attendants. The crew were friendly and made for a straightforward flight. Seats were fine, but the aircraft needs to go in for cabin maintenance. The air nozzles overhead were all loose and could not be closed or adjusted.

Head rest did not move, very uncomfortable. Staff was great. There was no entertainment, would be nice not to have to pay for snack.

Worst airline - on our flight down from MCO to EYW, there was a huuuuuge delay. We were supposed to take off 12p and it was pushed back to almost 2:30p. We boarded the plane and then sat on the tarmac forever because we were "over" weight and had to burn fuel. Rather than ask guests to volunteer and leave, they kept us on the plane. Finally a family decided to off board and take their luggage with them. Shortly after, we left the terminal but then the pilot told us we may have to sit at the end of the runway for 15-20mins to burn more fuel. Which we ended up doing and of course it started to rain. We finally took off 2:50p. We were supposed to land 1p and didn't land until 3:45p. Basically had time to scramble off the plane, grab our luggage, request transportation to our hotel, unpack, rinse off and hustle over to our 6:30p dinner ressy. It's a shame Breeze is the only non-stop airline from MCO to EYW. For this, not sure I'd ever go back to EYW - most def will not take Breeze again.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

Worst flight experience ever flights canceled. JetBlue told us just did not even bother standing in line to come back in one and a half hours then without any information we had to go pick up all of our luggage and spend over $2000 in accommodation just to get home. JetBlue said that the next flight available for us to get home would be three days later. Absolutely absurd hasn’t offered to give us any compensation do not fly JetBlue horrible company. They said it was based on the weather and the weather is great in all locations that we would’ve been flying to total hoax. I think it’s a conspiracy theory.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

Communication since no reason or explanation was given for 3 hrs delay

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.

I liked how when I got on board how fast we ended up taking off but what I truly disliked was how uncomfortable the seats were. There was truly never a time that I could ever get comfortable during both of my flights. The seats could get away during shorter flights but flights 3 hour plus makes it hard to enjoy.

The crew was great and the flight was very smooth. Can’t really judge food since I did not get any because it costs money. The seat was comfortable for what we bought. Thanks!

Crew was great. No entertainment and food and beverage was for purchase only, even water

It was canceled. The flight wasn’t rescheduled, everyone had to figure out their own new arrangements. They said we would get refunded our original fare and receive an additional $150. We received links for $100 only and they expired before we could activate them.

The plane had originated in Las Vegas at 6:30 in the morning and flew to Moline where we boarded. The flight left around 12:30 PM and there were no boxed snacks available and many of the alcoholic beverages were unavailable. I would find it hard to believe that that many of the passengers coming from Las Vegas at 6:30 in the morning, drank and ate that much of the items. I can only come to the conclusion that someone failed to stock the plane for the round-trip. This is a huge revenue failure for the airline and disappointment for the passengers. The flight crew did not seem happy to be there and did not engage with passengers. Allegiant you can do better.

They did not let my husband on the plane with our service animal at the last minute. Do NOT fly this airline with a service animal!

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

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.

Excessive fees for flight delays. What a Scam. I was not able to attend the wedding I needed to go.

It was terrible, we had to board and unboard the flight with a hour delay that caused me to miss an appointment and a surprise for my wife

Great! I intend to use Spirit for future flights. No complaints .

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Very easy boarding! Crew was fantastic and offered us refreshments quickly and efficiently. Quick, nice flight!

My baggage broke and they did not offer me anything. No conversation

It was not good at all, I think the crew could be kinder

Cheap flight but really uncomfortable. Seat cushions flimsy. Jammed in middle seat when flight is not full. They don’t even give you water

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

2 hour delay due to late plane, wrong size plane causing overbooking, and people getting off and on the plane after boarding was completed.

Since you have to pay for overhead bags then they shouldn't be running out of space and asking individuals who paid to remove stuff from the overhead

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

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!

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.