Cheap flights To Pawling (SWF) from $51

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Cheap Flights to Pawling from $51 One Way, $109 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 6 - Sat, May 9
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$109 Roundtrip, found 5 days ago
$109
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, May 6 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, May 9, priced at $109 found 5 days ago
Wed, Jun 17 - Sat, Jun 20
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$118 Roundtrip, found 6 days ago
$118
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Wed, Jun 17 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Jun 20, priced at $118 found 6 days ago
Fri, Sep 4 - Mon, Sep 7
CHS
Charleston Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 5 days ago
$122
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 4 from Charleston Intl. to Stewart Intl., returning Mon, Sep 7, priced at $122 found 5 days ago
Wed, Jun 3 - Wed, Jun 10
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$123 Roundtrip, found 5 days ago
$123
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 3 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 10, priced at $123 found 5 days ago
Fri, Sep 4 - Mon, Sep 7
CHS
Charleston Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 5 days ago
$127
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 4 from Charleston Intl. to Stewart Intl., returning Mon, Sep 7, priced at $127 found 5 days ago
Fri, May 22 - Mon, May 25
CHS
Charleston Intl.
SWF
Stewart Intl.
$129 Roundtrip, found 4 days ago
$129
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, May 22 from Charleston Intl. to Stewart Intl., returning Mon, May 25, priced at $129 found 4 days ago
Wed, Jun 3 - Wed, Jun 10
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 3 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 10, priced at $130 found 5 days ago
Fri, Sep 4 - Mon, Sep 7
CHS
Charleston Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 4 from Charleston Intl. to Stewart Intl., returning Mon, Sep 7, priced at $132 found 5 days ago
Wed, Aug 5 - Sat, Aug 8
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Aug 5 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Aug 8, priced at $133 found 5 days ago
Wed, Jun 10 - Wed, Jun 17
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$134 Roundtrip, found 3 days ago
$134
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jun 10 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 17, priced at $134 found 3 days ago

Pawling Flight Information

Traveling To
Pawling
Destination Airport IATA Code
SWF
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$109
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Pawling economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
2.5-star property

Hotel St. James

May 7 - May 11

4 night stay

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • Coach
Price was $1,030, price is now $543 per person
$543
per person
found 1 day ago
Park Lane New York
5.0-star property

Park Lane New York

Apr 23 - Apr 27

4 night stay

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Coach

Newark Liberty Intl. Airport (EWR) to Atlanta (ATL)

Frontier Airlines • Coach
Price was $1,271, price is now $743 per person
$743
per person
found 1 day ago
WestHouse New York
5.0-star property

WestHouse New York

May 6 - May 14

8 night stay

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

United • Coach

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

Frontier Airlines • Coach
Save 100% on your flight
Price was $2,808, price is now $1,660 per person
$1,660
per person
found 19 hours ago
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Pawling premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel St. James
2.5-star property

Hotel St. James

8.8/10 Excellent! (7,026 reviews)

May 8 - May 11

3 night stay

Raleigh (RDU) to Newark Liberty Intl. Airport (EWR)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $922, price is now $592 per person
$592
per person
found 1 day ago
Walking distance to many places, perfect location

Reviewed on Feb 13, 2026

Millennium Hotel Broadway Times Square
4.0-star property

Millennium Hotel Broadway Times Square

7.8/10 Good! (6,615 reviews)

May 13 - May 17

4 night stay

Detroit (DTW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,235, price is now $842 per person
$842
per person
found 1 day ago
Clean room excellent service

Reviewed on Mar 4, 2026

PUBLIC, an Ian Schrager hotel
4.0-star property

PUBLIC, an Ian Schrager hotel

8.6/10 Excellent! (3,443 reviews)

May 13 - May 17

4 night stay

Detroit (DTW) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,892, price is now $1,318 per person
$1,318
per person
found 1 day ago
Amazing location and property

Reviewed on Nov 20, 2025

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Pawling first class flight packages

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

Hotel Riu Plaza Manhattan Times Square

9.2/10 Wonderful! (3,450 reviews)

May 11 - May 13

2 night stay

Raleigh (RDU) to Newark Liberty Intl. Airport (EWR)

American Airlines • FirstClass

Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)

Delta • FirstClass
Price was $1,229, price is now $958 per person
$958
per person
found 1 day ago
Got in early, Checked in early, left the bags and went to visit World Trade One . room was available at 2 PM. It was a short 24 hour trip to New York , so essentially room was needed just ro sleep in it, It was great, the view from the second highest floor in hotel was nice .

Reviewed on Feb 5, 2026

Park Lane New York
5.0-star property

Park Lane New York

8.4/10 Very Good! (1,758 reviews)

Apr 22 - Apr 26

4 night stay

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

American Airlines • Non-stop roundtrip • FirstClass
Price was $2,465, price is now $1,884 per person
$1,884
per person
found 1 day ago
Will stay here again

Reviewed on Aug 24, 2025

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (2,931 reviews)

May 11 - May 13

2 night stay

Raleigh (RDU) to Newark Liberty Intl. Airport (EWR)

American Airlines • FirstClass

Newark Liberty Intl. Airport (EWR) to Raleigh (RDU)

Delta • FirstClass
Price was $1,262, price is now $977 per person
$977
per person
found 1 day ago
Beautiful room and great customer service

Reviewed on Feb 7, 2026

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Pawling

Traveling to Pawling and need a cheap flight? Orbitz has great deals on flights to Pawling right now. Plus, we offer big discounts on hotel rooms and car rentals for a great money-saving trip.

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Orbitz takes pride in providing the best customer experience possible, and that effort doesn't end with discount flights to Pawling or user-friendly mobile apps and web tools. Orbitz Customer Service is always ready to answer questions and help you with booking, planning, or canceling your Pawling flights. When you need us, we’re here for you!

Frequently asked questions

Which airlines fly to Pawling?
Reserving a flight to Pawling is easy — simply choose from 20 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 $109 and $134. If you were traveling one-way out of Raleigh (RDU), you could have snapped up fares from as low as $51.
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.