Cheap flights To Pawling (SWF)

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Pawling Flight Information

Traveling To
Pawling
Destination Airport IATA Code
SWF
Number of Airlines Serving
Airlines
Flight Price
Earliest Departing Flight
Latest Departing Flight

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Pawling economy flight packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Central Park
5.0-star property

1 Hotel Central Park

Jul 8 - Jul 12

4 night stay

Los Angeles (LAX) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $2,538, price is now $1,701 per person
$1,701
per person
found 1 day ago
Casa Francesca 6BR Villa & Heated Pool
3.5-star property

Casa Francesca 6BR Villa & Heated Pool

Jul 3 - Jul 11

8 night stay

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

JetBlue Airways • Coach

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

Frontier Airlines • Coach
Price was $19,568, price is now $12,676 per person
$12,676
per person
found 24 hours ago
Montauk Yacht Club
4.0-star property

Montauk Yacht Club

Jul 2 - Jul 6

4 night stay

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $3,374, price is now $2,228 per person
$2,228
per person
found 12 hours ago
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Pawling premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Row NYC
4.0-star property

Row NYC

7.6/10 Good! (69 reviews)

Jul 8 - Jul 12

4 night stay

Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)

United • PremiumEconomy

Newark Liberty Intl. Airport (EWR) to Los Angeles (LAX)

Frontier Airlines • PremiumEconomy
Price was $1,603, price is now $1,342 per person
$1,342
per person
found 9 hours ago
Great location, clean & helpful staff The room was small but that is New York!

Reviewed on May 3, 2026

Lotte New York Palace
4.5-star property

Lotte New York Palace

9/10 Wonderful! (2,059 reviews)

Jun 30 - Jul 3

3 night stay

Los Angeles (LAX) to New York (JFK)

American Airlines • Roundtrip • PremiumEconomy
Price was $2,360, price is now $1,968 per person
$1,968
per person
found 10 hours ago
Location! Location! Location!

Reviewed on Apr 26, 2026

Hyatt Regency Jersey City on the Hudson
4.0-star property

Hyatt Regency Jersey City on the Hudson

8.4/10 Very Good! (1,674 reviews)

Jul 8 - Jul 12

4 night stay

Los Angeles (LAX) to New York (JFK)

United • PremiumEconomy

New York (JFK) to Los Angeles (LAX)

Frontier Airlines • PremiumEconomy
Price was $2,092, price is now $1,749 per person
$1,749
per person
found 9 hours ago
Clean room as pictured

Reviewed on Apr 3, 2026

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Pawling first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,026 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Price was $1,060, price is now $796 per person
$796
per person
found 1 day ago
There was unexpected extra fees

Reviewed on May 10, 2026

42 Hotel
3.5-star property

42 Hotel

9/10 Wonderful! (873 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • FirstClass
Price was $956, price is now $800 per person
$800
per person
found 1 day ago
Hotel/Room was clean and well kept. Staff were very nice. Walking distance to public transportation and lots of food options.

Reviewed on Feb 25, 2025

Nova Hotel JFK
2.0-star property

Nova Hotel JFK

7.6/10 Good! (319 reviews)

Jul 11 - Jul 13

2 night stay

Chicago (ORD) to New York (JFK)

American Airlines • Roundtrip • FirstClass
Price was $1,247, price is now $1,063 per person
$1,063
per person
found 1 day ago
Did not have breakfast.

Reviewed on Dec 30, 2025

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Pawling

Why search for low cost fares on your flights to Pawling when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Pawling

Orbitz offers massive discounts and substantial last-minute savings on your Pawling flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

Cutting-Edge Mobile Tools to Keep You In The Know

Orbitz sends you free alerts and updates on your Pawling flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Pawling. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Pawling but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Pawling?
Reserving a flight to Pawling is easy — simply choose from airlines that fly into Westchester County Airport (HPN). When you've arranged your sightseeing itinerary and packed your suitcase, these leading domestic carriers will happily welcome you on board:

  • JetBlue - 243 flights to Pawling per month
  • American Airlines - 187 flights to Pawling per month
  • Delta - 153 flights to Pawling per month

What is the best airport to fly to in Pawling?
Stewart Intl. Airport (SWF). It's the city's main terminal and is situated around 25 miles west of the downtown area. You'll be dropping off your bags and exploring the best of Pawling not long after flying in.
How much is a flight to Pawling?
Prices for return flights to Pawling this past week fluctuated between and . If you were traveling one-way out of (), you could have snapped up fares from as low as .
How to book the cheapest flight to Pawling?
Picking up cheap flights to Pawling is as simple as booking your ticket with Orbitz. But if you'd love to make sure you're nabbing the best flight deals around, here are a few tips to keep in mind:

  • Taking off from or landing at nearby airports may work out to be cheaper. Enter your preferred departure and arrival points. Next, click on the 'Nearby airports' function below to see your options.
  • If you're flexible with when you fly out, click on the 'Show flexible dates' link. You'll see the flight deals for the days either side of your chosen departure. Fares often vary depending on the day of the week.
  • To fine tune your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also choose the time of day you'd like to fly under 'Sort & Filter' to the left.
  • Book your fare as soon as you've sorted your travel dates. While it does happen now and then, tickets rarely get cheaper as your departure date gets closer.
  • Combine your flights, hotels and car rental into a value-for-money package deal. Save your hard-earned dollars for things that really excite you, like discovering every corner of Pawling.
  • Don't fly during the busy season if possible. By avoiding summer, school vacations and other popular dates, you can save a significant amount on your airfares.

What is the best time to book a flight to Pawling?
Purchase your seats to Pawling in January. This is the perfect time of the year for low prices, closely followed by February and August. Score cheap flights and let your dream vacation come true with Orbitz.
What day of the week is the cheapest to book a flight to Pawling?
Typically, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book flights to Pawling. If you're looking for the best airfares, search across those days and you're likely to score an excellent flight deal.
What is the cheapest day of the week to fly to Pawling?
You can score cheap flights to Pawling by hopping on a plane on a Monday, according to Orbitz data from 2020. Tuesday is the next most affordable day, while Saturday has the most costly ticket prices. Whether you prefer to stretch your travel budget or take off on whichever day is convenient, you'll always get a wonderful deal with Orbitz.
What is the cheapest month to fly to Pawling?
To book cheap flights to Pawling, you should fly out in August. If saving big on your ticket is your main priority, Orbitz data shows that this is generally an excellent month to go on a trip. June is when fares are the least affordable.
Which airlines allow free cancellation?
If you're concerned your travel plans could change, Orbitz will help you lock in a flexible fare. All you have to do is select "Filter by flexible change policies" when searching for your Pawling flights. We'll show you carriers that include free cancellation and no change fees — along with our famous low prices.
What do I need for the flight to Pawling?
The secret to a comfortable and successful flight is being well prepared. Here are some handy tips to help you get ready for take off:

  • Your travel documents are the most important items you'll need to have with you on your flight to Pawling. To avoid any problems when checking in, make sure that the personal information on your ticket matches your government-issued photo ID.
  • Take some activities to keep you entertained on your trip to Pawling. Books and electronic gadgets like tablets and e-readers are all good. Be sure to take a water bottle with you too. Even on short flights, it's important to remain well-hydrated.
  • Whatever the weather outside, plane cabins can get cold. Bring a light jacket on board to keep yourself warm and cozy.

How many direct flights are there to Pawling?
With 7 flights traveling directly to Pawling each month, it won't be too hard to find one that matches your schedule. A range of carriers fly nonstop to this location, including Frontier Airlines, Fly Play and Allegiant Air.
How do I get cheap first-class/business deals to Pawling?
There are ways of booking first or business-class airfares to Pawling that won't burn through your budget. Snap up a seat in the pointy end of the plane for less with these helpful tips:

  • Be more flexible with your travel dates and hold out for exclusive offers or sales on first or business-class airfares.
  • Look for a budget carrier that has business-class seats. They often come with more space and a glass of bubbly — but without the premium price.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat at the front of the plane. You may also be able to upgrade with points earned through a loyalty scheme.

What is the best time to go to Pawling?
There's no right or wrong time to go to Pawling, but January, August and October are the liveliest months. For most places in the Northern Hemisphere, summertime begins June 20. If you'd prefer to spend most of your days in a lightweight top than a winter jacket, this time of the year would suit you perfectly. Expect average daytime highs of 80 ºF and nighttime lows around 60 ºF.
Travel tips for Pawling

  • John Kane House is one of this buzzing city's most popular attractions. Book a room near the downtown area and check it out anytime you please.
  • If you're in the mood to venture a bit farther afield and check out more Pawling sights, pick up the keys to a car rental and make tracks to Woodbury Common Premium Outlets. It won't take long to drive to from downtown.
  • When it's time to see more amazing destinations in Dutchess County, hop back in the car and drive toward Red Hook. One of the region's other important cities, the possibilities for fun are endless here.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.