$53 Cheap Flights to Pawling, NY

Popular airlines to Pawling

How much is the cheapest flight to Pawling?

Prices were available within the past 7 days and start at $53 for one-way flights and $112 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Breeze Airways
Breeze Airways
Fly Play
World Ticket Ltd

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

April is typically the cheapest month to fly

From $139 - $256 per traveler.

Graph displaying average flight prices per month

Tips to find the cheapest flights to Pawling

The cheapest day to fly

Get started finding a cheap flight to Pawling 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

September is the cheapest month to fly to Pawling. 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 Pawling. 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 Pawling, 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 Pawling

The lowest price for round-trip flights to Pawling in 2025 starts from from $112, while one-way tickets start from from $53. 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 Pawling. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Pawling

Breeze Airways, Fly Play, World Ticket Ltd are just some of the airlines that can typically offer cheap tickets to Pawling. 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 Pawling and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Pawling, 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 Pawling. 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 Pawling 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 Pawling

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 Pawling.

Stopover savings

The cheapest tickets to Pawling are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Pawling. 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 Pawling 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 Pawling. Simply download the free Expedia app to your smart device and activate Pawling 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 Pawling. 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 Pawling?
The least expensive month for flights to Pawling is usually September *. Set your travel dreams in motion without spending a fortune by flying when fares are at their lowest. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
Which US cities have the cheapest flights to Pawling?
Land cheap flights to Pawling from West Palm Beach, Atlanta and Charlotte. These cities generally offer the best fares to this much-loved destination. But keep in mind that seasonality, demand and stopovers will also have an impact on rates, so stay flexible and book when you see a bargain.
Which US cities fly direct to Pawling?
There are 16 US destinations that you can fly to Pawling nonstop from. Explore your options by using the "Direct flights only" filter on Expedia and find the best departure point for your trip. Here are several of the top cities to set off from:

  • West Palm Beach
  • Atlanta
  • Charlotte
  • Orlando
  • Washington

How to find a cheap flight to Pawling?
Book well in advance or look for cheap flights to Pawling during off-peak months like March and August. Jetting off on a Thursday could also save you 16% on average compared to a Sunday flight.* The Expedia app makes it even easier to know when to book. Just activate the toggle for "Watch prices" and get notified as soon as fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Pawling?
Staying flexible with your plans may help you to find last-minute deals on cheap flights to Pawling. To view all the available options, consider exploring different ticket types, changing your Pawling vacation dates, jetting out of an alternative airport or using another airline.
How far in advance should I book a flight to Pawling?
Find the departure dates you want and a fare that works with your budget by booking your domestic flight to Pawling up to 28 days in advance. Lock in tickets two to four months ahead if you're traveling to Pawling from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Pawling?
You can generally find cheap flights to Pawling on a Sunday. You can save about 8% on average compared to those who book on a Friday, which is typically the most expensive day to book.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Pawling?
There are 7 airlines connecting Pawling with 73 airports all over the world. The key point of arrival to this city is LaGuardia Airport (LGA). Travel with any of these popular airlines to Pawling:

  • United Airlines
  • Delta Air Lines
  • Air Canada
  • American Airlines

Where do you fly into Pawling?
The main airport when you fly to Pawling is Stewart Intl. Airport (SWF), but there are some great nearby alternatives like Westchester County Airport (HPN) and Tweed - New Haven Regional Airport (HVN). You can also land at Bradley Intl. Airport (BDL) and LaGuardia Airport (LGA) when flying to Pawling.
How far is the airport from central Pawling?
You'll be about 25 mi west of central Pawling after arriving at Stewart Intl. Airport (SWF).
Can I save money by booking a Pawling trip package?
Bundle your hotel and flight and you could save hundreds of dollars. Better yet, you can add extras like activities and car rentals to your Pawling flight and hotel package deal. With Expedia, it's a breeze to look after all your Pawling travel plans in the same place.
Can I change or cancel my flight to Pawling?
If you bought your flight to Pawling within the last 24 hours, you can usually change or cancel it for free. After that, additional charges may apply depending on the airline's terms and conditions. For more information, head to our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may receive a credit toward future travel rather than a direct refund. When searching on Expedia, use the "No cancel fee" or "Changes included" boxes to compare tickets with flexible change policies.
Flights to Pawling information
Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Destination city name
Newburgh
Roundtrip price
$111

Trending flights to Pawling

Prices were available within the past 7 days and start at $53 for one-way flights and $112 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways

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*Available to One Key members.