Cheap flights To Pawling (SWF) from $52

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Cheap Flights to Pawling from $52 One Way, $76 Round Trip

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

Fri, Jan 30 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$76 Roundtrip, found 2 days ago
$76
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $76 found 2 days ago
Fri, Jan 23 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$95 Roundtrip, found 2 days ago
$95
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 23 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $95 found 2 days ago
Fri, Jan 30 - Sun, Feb 1
MCO
Orlando Intl.
SWF
Stewart Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Sun, Feb 1, priced at $100 found 1 day ago
Fri, Jan 30 - Mon, Feb 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$103 Roundtrip, found 2 days ago
$103
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 9, priced at $103 found 2 days ago
Fri, Jan 30 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$104 Roundtrip, found 2 hours ago
$104
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $104 found 2 hours ago
Fri, Jan 30 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $108 found 1 day ago
Fri, Jan 30 - Mon, Feb 2
MCO
Orlando Intl.
SWF
Stewart Intl.
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 2, priced at $111 found 4 days ago
Wed, May 6 - Sat, May 9
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$112 Roundtrip, found 5 days ago
$112
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 $112 found 5 days ago
Fri, Feb 6 - Sun, Feb 8
MCO
Orlando Intl.
SWF
Stewart Intl.
$113 Roundtrip, just found
$113
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Feb 6 from Orlando Intl. to Stewart Intl., returning Sun, Feb 8, priced at $113 just found
Fri, Jan 30 - Mon, Feb 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Jan 30 from Orlando Intl. to Stewart Intl., returning Mon, Feb 9, priced at $115 just found

Pawling Flight Information

Traveling To
Pawling
Destination Airport IATA Code
SWF
Number of Airlines Serving
Airlines
Breeze Airways
Flight Price
$76
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.
Margaritaville Resort Times Square
4.0-star property

Margaritaville Resort Times Square

Jan 23 - Jan 25

2 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Coach

New York (JFK) to Atlanta (ATL)

Spirit Airlines • Coach
Price was $422, price is now $241 per person
$241
per person
found 1 day ago
The Inn At Fox Hollow Hotel
4.0-star property

The Inn At Fox Hollow Hotel

Jan 29 - Feb 3

5 night stay

Dallas (DFW) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Price was $939, price is now $482 per person
$482
per person
found 1 day ago
Harpoon House
3.0-star property

Harpoon House

Jan 30 - Feb 1

2 night stay

Dallas (DFW) to New York (JFK)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $542, price is now $333 per person
$333
per person
found 17 hours ago
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Pawling premium economy flight packages

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

Hotel Beacon

9.4/10 Exceptional! (1,350 reviews)

Feb 13 - Feb 15

2 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $805, price is now $621 per person
$621
per person
found 1 day ago
The staff upon arrival ere friendly and very funny. I had a great time during my stay.

Reviewed on Apr 13, 2025

Pendry Natirar
5.0-star property

Pendry Natirar

9.8/10 Exceptional! (7 reviews)

Jan 26 - Jan 30

4 night stay

Miami (MIA) to New York (NYC)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,262, price is now $1,680 per person
$1,680
per person
found 22 hours ago
Newark Liberty International Airport Marriott
4.0-star property

Newark Liberty International Airport Marriott

8.6/10 Excellent! (1,010 reviews)

Jan 26 - Jan 30

4 night stay

Miami (MIA) to Newark Liberty Intl. Airport (EWR)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,103, price is now $864 per person
$864
per person
found 22 hours ago
Typical for an airport hotel - everything g you would expect !

Reviewed on Dec 8, 2025

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Pawling business class flight packages

Price found within the past 48 hours. Click for updated prices.
Courtyard New York Manhattan/ Midtown East
3.0-star property

Courtyard New York Manhattan/ Midtown East

9/10 Wonderful! (2,346 reviews)

Feb 12 - Feb 15

3 night stay

Los Angeles (LAX) to New York (JFK)

American Airlines • Roundtrip • BusinessClass
Price was $3,503, price is now $3,013 per person
$3,013
per person
found 1 day ago
The staff was always professional and friendly.

Reviewed on Oct 6, 2025

The Langham, New York, Fifth Avenue
5.0-star property

The Langham, New York, Fifth Avenue

9.4/10 Exceptional! (1,001 reviews)

Feb 12 - Feb 15

3 night stay

Los Angeles (LAX) to New York (JFK)

American Airlines • Roundtrip • BusinessClass
Price was $3,742, price is now $3,295 per person
$3,295
per person
found 1 day ago
Hospitality room was top notch!

Reviewed on Dec 8, 2025

Lotte New York Palace
4.5-star property

Lotte New York Palace

9/10 Wonderful! (1,784 reviews)

Feb 12 - Feb 15

3 night stay

Los Angeles (LAX) to New York (JFK)

American Airlines • Roundtrip • BusinessClass
Price was $3,582, price is now $3,167 per person
$3,167
per person
found 1 day ago
We stay here almost very year and would not think of staying anywhere else!

Reviewed on Jun 15, 2025

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Pawling first class flight packages

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

Allegria Hotel

7.8/10 Good! (1,261 reviews)

Jan 21 - Jan 25

4 night stay

Dallas (DFW) to New York (JFK)

Delta • Non-stop roundtrip • FirstClass
Price was $1,288, price is now $1,119 per person
$1,119
per person
found 1 day ago
For an off season stay, I am very impressed with how clean and professionally staffed the hotel is. Thank you for a wonderful mini vacation!

Reviewed on Nov 30, 2025

Chateau Grande Hotel
3.5-star property

Chateau Grande Hotel

8.6/10 Excellent! (242 reviews)

Jan 30 - Feb 3

4 night stay

Dallas (DFW) to New York (NYC)

United • Non-stop roundtrip • FirstClass
Price was $1,592, price is now $1,326 per person
$1,326
per person
found 21 hours ago
I do wish they had breakfast included or available

Reviewed on Mar 12, 2022

Hilton Short Hills
4.0-star property

Hilton Short Hills

8.4/10 Very Good! (1,000 reviews)

Jan 26 - Jan 30

4 night stay

Miami (MIA) to Newark Liberty Intl. Airport (EWR)

United • Non-stop roundtrip • FirstClass
Price was $1,320, price is now $1,154 per person
$1,154
per person
found 22 hours ago
It was clean, quiet and safe.

Reviewed on Aug 22, 2025

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Pawling

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Pawling flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Pawling again.

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Low Prices for Pawling Flights

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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 $76 and $115. If you were traveling one-way out of Orlando (MCO), 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.