$25 Cheap Flights to Pleasantville, NY

View $25 flight on Wed, Mar 4, 2026Opens in a new window

Popular airlines to Pleasantville

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Today's featured flight deals to Pleasantville

Nonstop
Carry-on included
Lower price than typical

How much is the cheapest flight to Pleasantville?

Prices were available within the past 7 days and start at $25 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Mar 3 - Wed, Mar 4
MCO
Orlando
LGA
New York
$52 Roundtrip, just found
$52
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Mar 3 from Orlando to New York, returning Wed, Mar 4, priced at $52 just found
Frontier Airlines
Wed, Mar 4 - Wed, Mar 11
MCO
Orlando
LGA
New York
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Mar 4 from Orlando to New York, returning Wed, Mar 11, priced at $58 just found
Breeze Airways
Fri, Mar 6 - Mon, Mar 9
MCO
Orlando
HPN
White Plains
$113 Roundtrip, found 16 hours ago
$113
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Fri, Mar 6 from Orlando to White Plains, returning Mon, Mar 9, priced at $113 found 16 hours ago
American Airlines
Fri, May 8 - Sun, May 10
MCO
Orlando
LGA
New York
$127 Roundtrip, just found
$127
Roundtrip
just found
Select American Airlines flight, departing Fri, May 8 from Orlando to New York, returning Sun, May 10, priced at $127 just found
JetBlue Airways
Fri, May 8 - Sun, May 10
MCO
Orlando
LGA
New York
$127 Roundtrip, just found
$127
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, May 8 from Orlando to New York, returning Sun, May 10, priced at $127 just found

Alternative airports near Pleasantville

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to LaGuardia LGA. Cheapest option available. Average driving time to city center is 44 minutes. Flights from $160
LGA
LaGuardia
Cheapest
Average driving time to city center44 min
Flights from $160
Select flight to Westchester County HPN. Closest option available. Average driving time to city center is 15 minutes. Flights from $234
HPN
Westchester County
Closest
Average driving time to city center15 min
Flights from $234

Find the cheapest month to fly from Columbus (CMH) to New York (JFK)

September is typically the cheapest month to fly

From $139 - $338 per traveler.

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Tips to find the cheapest flights to Pleasantville

The cheapest day to fly

Get started finding a cheap flight to Pleasantville on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

March is the cheapest month to fly to Pleasantville. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Pleasantville. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Pleasantville, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Pleasantville

The lowest price for round-trip flights to Pleasantville in 2026 starts from from $52, while one-way tickets start from from $25. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Pleasantville. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Pleasantville

Spirit Airlines, Frontier Airlines, Breeze Airways, JetBlue Airways, Southwest Airlines, American Airlines are just some of the airlines that can typically offer cheap tickets to Pleasantville. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Pleasantville and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Pleasantville, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Pleasantville. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Pleasantville plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Pleasantville

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Pleasantville.

Stopover savings

The cheapest tickets to Pleasantville are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Pleasantville. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Pleasantville for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Pleasantville. Simply download the free Expedia app to your smart device and activate Pleasantville flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Pleasantville. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

What month is the cheapest to fly to Pleasantville?
September is the cheapest month to fly to Pleasantville, with average fares around $439. This month often has less travel activity, which helps keep prices lower. Additionally, January, February, and March are also good months for budget travelers.*Prices based on flights available on Expedia in the last year.
Which US cities have the cheapest flights to Pleasantville?
Looking for affordable flights to Pleasantville? Consider flying from these US cities:

  • Vero Beach (VRB)
  • Pittsburgh (PIT)
  • Worcester (ORH)
  • Fayetteville (FAY, XNA)
  • Flint (FNT)

with prices usually starting around $71.
Which US cities fly direct to Pleasantville?
Several US cities offer direct flights to airports serving Pleasantville. Here are the options:To Liberty Intl. (EWR)
  • Los Angeles (LAX)
  • Orlando (MCO)
  • Atlanta (ATL)
  • Fort Lauderdale (FLL)
  • Chicago (MDW, ORD)

To John F. Kennedy Intl. (JFK)
  • Los Angeles (LAX)
  • San Francisco (SFO)
  • Orlando (MCO)
  • Atlanta (ATL)
  • Fort Lauderdale (FLL)

To LaGuardia (LGA)
  • Chicago (MDW, ORD)
  • Atlanta (ATL)
  • Fort Lauderdale (FLL)
  • Orlando (MCO)
  • Dallas (DAL, DFW)

How to find a cheap flight to Pleasantville?
To find a cheap flight to Pleasantville, be flexible with your dates. Traveling in the off-season or shoulder season can help you save. Mid-week flights are usually less expensive, too. Use flight search engines, like Expedia, to compare airlines, flight times and routes all in one place to find affordable rates. You may find that flights with layovers are cheaper than direct flights. You can also set up Price Tracking and receive alerts when fares go up or down.
Which airlines fly to Pleasantville?
You can fly to Pleasantville with several airlines:

  • American Airlines
  • Delta
  • Delta Air Lines
  • Frontier Airlines
  • JetBlue Airways
  • Spirit Airlines
  • United
  • United Airlines

Where do you fly into Pleasantville?
If you're heading to Pleasantville, you have several airport options:

  • The closest major airport is New York, NY (JFK-John F. Kennedy Intl.), about 34 miles from the city center, which is a hub for JetBlue Airways, American Airlines, and Delta, with other airlines like British Airways, Avianca also operating here.
  • Newark Liberty Intl. Airport (EWR) is another option, about 41 miles away, serving as a hub for United, Spirit Airlines, and American Airlines, with Delta, Air Canada also operating here.
  • New York, NY (LGA-LaGuardia), about 25 miles away, serving as a hub for Spirit Airlines, American Airlines, and Delta, with United, Air Canada also operating here.
  • Hartford, CT (BDL-Bradley Intl.), about 94 miles away, serving as a hub for American Airlines, Delta, and United, with WN, JetBlue Airways also operating here.
  • White Plains, NY (HPN-Westchester County), about 8 miles away, serving as a hub for American Airlines, Delta, and JetBlue Airways, with MX, Tradewind Aviation also operating here.

What is the cheapest airport to fly to in Pleasantville?
When visiting Pleasantville, the cheapest airport is typically New York, NY (JFK-John F. Kennedy Intl.), which is about 34 miles from downtown. This can be a great way to save on your travel expenses.*Prices based on flights available on Expedia in the last year.
Which budget airlines fly to Pleasantville?
For budget travel to Pleasantville, there are 15 low-cost airlines to choose from, including:

  • JetBlue Airways: serves White Plains (HPN), New York (LGA), New York (JFK), Newark (EWR), Hartford (BDL)
  • Spirit Airlines: serves New York (LGA), Newark (EWR), Hartford (BDL)
  • Frontier Airlines: serves New York (LGA), New York (JFK), Newark (EWR), Hartford (BDL)
  • Southwest Airlines: serves New York (LGA), New York (JFK), Hartford (BDL)
  • Breeze: serves White Plains (HPN), Newark (EWR), Hartford (BDL)
  • Arajet: flies to Newark (EWR)
  • Sun Country Airlines: serves New York (JFK), Newark (EWR), Hartford (BDL)
  • WestJet: serves White Plains (HPN), New York (LGA), New York (JFK), Newark (EWR), Hartford (BDL)
  • Viva Aerobus: flies to New York (JFK)
  • Volaris: flies to Newark (EWR)

What is the best month to visit Pleasantville?
The best month to visit Pleasantville depends on your priorities, whether you want ideal weather, fewer crowds, or the lowest prices. If affordability matters most, look for cheap March flights outside of peak season.
How far in advance should I book a flight to Pleasantville?
For domestic travel to Pleasantville, booking around 1 month in advance typically offers lower prices. For international flights to Pleasantville, aim to book around 1 month ahead if you want the best prices. For added peace of mind, use Expedia's Price Drop Protection™ when you make your booking. It's free to use for Gold and Platinum members on the Expedia app. Once a qualifying flight is purchased, we'll automatically check your flight on Expedia until the day of your departure and notify you if there are price changes. If your flight price drops after you book, we'll automatically award the price difference in OneKeyCash™* into your One Key account after your trip ends.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What day of the week is cheapest day to buy a plane ticket to Pleasantville?
Friday is typically the cheapest day to buy a plane ticket to Pleasantville, with an average fare of around $441. If you're flexible, consider this day to maximize your savings, as Mondays are generally the most expensive. Use Expedia's Price Tracking tool to monitor prices for your trip and receive alerts when fares go up or down.*Cheapest day to book based on flights available on Expedia in the last year.
What is the most expensive month to fly to Pleasantville?
December is the most expensive month to fly to Pleasantville, with average return ticket prices around $547. This is about 14% higher than the average throughout the year, as many travelers take to the skies for the holidays. If you're looking for lower fares, consider traveling in February or September.*Prices based on flights available on Expedia in the last year.
How far is the airport from central Pleasantville?
You'll find 2 airports near Pleasantville:

  • White Plains, NY (HPN-Westchester County): 8 miles southeast
  • New York, NY (LGA-LaGuardia): 25 miles south

These options give you flexibility when planning your trip.
How can I track flight prices to Pleasantville?
Our Price Tracking tool allows you to monitor fares to Pleasantville. You can view flight price history and see predictions of future prices as available. When you're signed into your Expedia account, you can set up flight price alerts too. This way, you'll receive notifications when prices go up or down, so you know when it's the right time to book.
How to get a cheap last-minute flight to Pleasantville?
It is possible to find cheap, last-minute flights to Pleasantville, especially if you can be flexible with your dates, times and route. Whether you're planning a spontaneous getaway or need to travel for business, there are plenty of last-minute flight deals on Expedia. You can also bundle your flight and hotel for even more savings with a package deal.
Can I earn miles booking a flight to Pleasantville with Expedia?
You can earn miles when booking a flight to Pleasantville on Expedia. Before confirming your booking, just select the frequent flyer program name and enter your program number. For even more rewards, join One Key™—our free travel rewards program. One Key members earn OneKeyCash™* on eligible bookings for every dollar spent.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
Can I save money by booking a Pleasantville trip package?
Book a Pleasantville flight and hotel package deal on Expedia, and you can make significant savings. It's simple to bundle your accommodations and flights, and you can also add car rentals and activities to create your own customized Pleasantville trip. Plus, nothing beats the convenience of booking everything in the same place.
Can I change or cancel my flight to Pleasantville?
It's often possible to cancel or change your flight to Pleasantville using Expedia. Many airlines let you cancel your flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may offer to reschedule your flight rather than provide a direct refund. To find affordable flights to Pleasantville with flexible change policies, select "No cancel fee" or "Changes included" when you search. Need more information? Visit our Customer Service Portal.

*Flight schedules are subject to change.

Flights to Pleasantville information
Destination airport
LaGuardia
Destination airport IATA code
LGA
Destination city name
New York
Roundtrip price
$51

Trending flights to Pleasantville

Prices were available within the past 7 days and start at $25 for one-way flights and $52 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, Mar 3 - Wed, Mar 4
MCO
Orlando
LGA
New York
$52 Roundtrip, just found
$52
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Mar 3 from Orlando to New York, returning Wed, Mar 4, priced at $52 just found

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*Available to One Key members.