Cheap flights To Pawling (SWF) from $52

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Cheap Flights to Pawling from $52 One Way, $102 Round Trip

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

Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 8 hours ago
$102
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Sep 16, priced at $102 found 8 hours ago
Fri, Sep 11 - Mon, Sep 14
CHS
Charleston Intl.
SWF
Stewart Intl.
$107 Roundtrip, found 3 days ago
$107
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Charleston Intl. to Stewart Intl., returning Mon, Sep 14, priced at $107 found 3 days ago
Wed, Sep 16 - Sat, Sep 19
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 16 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Sep 19, priced at $107 found 1 day ago
Wed, Sep 23 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$112 Roundtrip, found 8 hours ago
$112
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Sep 23 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Sep 26, priced at $112 found 8 hours ago
Wed, Sep 23 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$117 Roundtrip, found 8 hours ago
$117
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Sep 23 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Sep 26, priced at $117 found 8 hours ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Stewart Intl., returning Sun, Sep 6, priced at $122 found 4 days ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$127 Roundtrip, found 2 days ago
$127
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Stewart Intl., returning Sun, Sep 6, priced at $127 found 2 days ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Stewart Intl., returning Sun, Sep 6, priced at $132 found 2 days ago
Wed, Sep 2 - Sun, Sep 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando Intl. to Stewart Intl., returning Sun, Sep 6, priced at $137 found 1 day ago
Wed, Sep 2 - Sun, Sep 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$142 Roundtrip, found 1 day ago
$142
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 2 from Orlando Intl. to Stewart Intl., returning Sun, Sep 6, priced at $142 found 1 day ago

Pawling Flight Information

Traveling To
Pawling
Destination Airport IATA Code
SWF
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$102
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.
The Muse New York
4.0-star property

The Muse New York

Aug 6 - Aug 10

4 night stay

Dallas (DAL) to Newark Liberty Intl. Airport (EWR)

Delta • Coach

Newark Liberty Intl. Airport (EWR) to Dallas (DAL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,019, price is now $616 per person
$616
per person
found 1 day ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Aug 6 - Aug 11

5 night stay

Dallas (DAL) to Newark Liberty Intl. Airport (EWR)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,820, price is now $1,134 per person
$1,134
per person
found 1 day ago
Sofitel New York
4.5-star property

Sofitel New York

Aug 6 - Aug 11

5 night stay

Dallas (DAL) to Newark Liberty Intl. Airport (EWR)

Delta • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,620, price is now $1,023 per person
$1,023
per person
found 1 day ago
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Pawling premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Manhattan-Midtown East
3.5-star property

Hilton Garden Inn New York/Manhattan-Midtown East

7.8/10 Good! (1,755 reviews)

Aug 1 - Aug 5

4 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,134, price is now $724 per person
$724
per person
found 8 hours ago
Ongoing construction had only one elevator cart took 20 minutes to get up and down. No stairs to go up

Reviewed on Feb 11, 2026

The Towers at Lotte New York Palace
5.0-star property

The Towers at Lotte New York Palace

9.2/10 Wonderful! (680 reviews)

Aug 6 - Aug 9

3 night stay

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

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,179, price is now $1,240 per person
$1,240
per person
found 2 hours ago
We had an absolute amazing experience at The Lotte Palace hotel . We were always greeted warmly by the doormen, concierge or any staff members. The rooms were comfortable and large by NYC standards. The views were incredible too. We loved our stay and will be back!

Reviewed on Mar 18, 2024

Hotel St. James
3.0-star property

Hotel St. James

8.8/10 Excellent! (7,435 reviews)

Aug 1 - Aug 5

4 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,174, price is now $772 per person
$772
per person
found 8 hours ago
We enjoyed the location but the experience wasn’t otherwise memorable.

Reviewed on Jun 13, 2026

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Pawling business 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! (3,593 reviews)

Aug 12 - Aug 15

3 night stay

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

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,462, price is now $1,088 per person
$1,088
per person
found 18 hours ago
Beds are comfortable

Reviewed on May 12, 2026

2 bedroom luxury Empire State VIEW
2.0-star property

2 bedroom luxury Empire State VIEW

10/10 Exceptional! (1 review)

Aug 12 - Aug 15

3 night stay

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

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $2,833, price is now $1,896 per person
$1,896
per person
found 17 hours ago
Park Lane New York
5.0-star property

Park Lane New York

8.4/10 Very Good! (1,818 reviews)

Aug 12 - Aug 15

3 night stay

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

Delta • BusinessClass

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

Frontier Airlines • BusinessClass
Price was $1,613, price is now $1,197 per person
$1,197
per person
found 1 day ago
No coffee in the room

Reviewed on Apr 29, 2026

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Pawling first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Manhattan-Midtown East
3.5-star property

Hilton Garden Inn New York/Manhattan-Midtown East

7.8/10 Good! (1,755 reviews)

Jul 31 - Aug 2

2 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • FirstClass
Price was $1,271, price is now $1,025 per person
$1,025
per person
just found
Ongoing construction had only one elevator cart took 20 minutes to get up and down. No stairs to go up

Reviewed on Feb 11, 2026

1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

9/10 Wonderful! (1,000 reviews)

Aug 6 - Aug 9

3 night stay

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

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,041, price is now $2,044 per person
$2,044
per person
found 2 hours ago
Best hotel experience in NYC over the past 10 tears, would highly recommend

Reviewed on Mar 17, 2026

2 bedroom luxury Empire State VIEW
2.0-star property

2 bedroom luxury Empire State VIEW

10/10 Exceptional! (1 review)

Aug 12 - Aug 15

3 night stay

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

Delta • FirstClass

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

Frontier Airlines • FirstClass
Save 100% on your flight
Price was $2,925, price is now $1,988 per person
$1,988
per person
found 24 hours ago
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Pawling

Save money on your flights to Pawling as well as on hotel and car packages.

 

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Mix and Match

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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 $102 and $142. If you were traveling one-way out of Charleston (CHS), you could have snapped up fares from as low as $52.
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.