$61 Cheap flight deals from Orlando (ORL) to Pawling (SWF)

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This Weekend's Flight Deals from Orlando to Pawling

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Mar 8 - Mon, Mar 9
MCO
Orlando Intl.
SWF
Stewart Intl.
$392 Roundtrip, just found
$392
Roundtrip
just found
Select Breeze Airways flight, departing Sun, Mar 8 from Orlando Intl. to Stewart Intl., returning Mon, Mar 9, priced at $392 just found

Airfares from $61 One Way, $129 Round Trip from Orlando to Pawling

Prices starting at $129 for return flights and $61 for one-way flights to Pawling were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 10 - Mon, Sep 14
MCO
Orlando
SWF
Newburgh
$129 Roundtrip, found 15 hours ago
$129
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando to Newburgh, returning Mon, Sep 14, priced at $129 found 15 hours ago
Thu, Sep 10 - Sun, Sep 13
MCO
Orlando
SWF
Newburgh
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando to Newburgh, returning Sun, Sep 13, priced at $132 found 4 days ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando
SWF
Newburgh
$134 Roundtrip, found 15 hours ago
$134
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando to Newburgh, returning Mon, Sep 14, priced at $134 found 15 hours ago
Thu, Sep 3 - Thu, Sep 10
MCO
Orlando
SWF
Newburgh
$137 Roundtrip, found 18 hours ago
$137
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando to Newburgh, returning Thu, Sep 10, priced at $137 found 18 hours ago
Wed, May 6 - Sat, May 9
MCO
Orlando
SWF
Newburgh
$139 Roundtrip, found 1 hour ago
$139
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Wed, May 6 from Orlando to Newburgh, returning Sat, May 9, priced at $139 found 1 hour ago

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

9.2/10 Wonderful! (3,941 reviews)

Apr 17 - Apr 19

2 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Spirit Airlines • Coach

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Frontier Airlines • Coach
Price was $808, price is now $458 per person
$458
per person
found 1 day ago
Great location! Very clean and the staff were super friendly. We really enjoyed our stay!

Reviewed on Dec 14, 2025

Sheraton Parsippany Hotel
4.0-star property

Sheraton Parsippany Hotel

8/10 Very Good! (1,003 reviews)

Apr 7 - Apr 14

7 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Southwest Airlines • Non-stop • Coach

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $899, price is now $593 per person
$593
per person
found 1 day ago
The hotel is outdated. Exterior is amazing, interior however needs an update. Shower did not work properly, rug look like it belonged in a 48hr episode and ironing board was broken. The staff however were friendly and pleasant. I would not stay there again for that price.

Reviewed on Aug 3, 2025

Outsite Chelsea
2.0-star property

Outsite Chelsea

8.8/10 Excellent! (72 reviews)

Apr 9 - Apr 12

3 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Southwest Airlines • Non-stop • Coach

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $820, price is now $544 per person
$544
per person
found 1 day ago
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Pawling packages with premium economy flights

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! (6,546 reviews)

Apr 23 - Apr 28

5 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,446, price is now $861 per person
$861
per person
found 1 day ago
Walking distance to many places, perfect location

Reviewed on Feb 13, 2026

Margaritaville Resort Times Square
4.0-star property

Margaritaville Resort Times Square

9.2/10 Wonderful! (3,941 reviews)

Apr 23 - Apr 28

5 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,742, price is now $1,024 per person
$1,024
per person
found 1 day ago
Great location! Very clean and the staff were super friendly. We really enjoyed our stay!

Reviewed on Dec 14, 2025

Lotte New York Palace
4.5-star property

Lotte New York Palace

9/10 Wonderful! (1,723 reviews)

Apr 23 - Apr 28

5 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,200, price is now $1,476 per person
$1,476
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.
Hotel St. James
2.5-star property

Hotel St. James

8.8/10 Excellent! (6,546 reviews)

Apr 10 - Apr 12

2 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • FirstClass
Price was $1,027, price is now $816 per person
$816
per person
found 1 day ago
Walking distance to many places, perfect location

Reviewed on Feb 13, 2026

Margaritaville Resort Times Square
4.0-star property

Margaritaville Resort Times Square

9.2/10 Wonderful! (3,941 reviews)

Apr 10 - Apr 12

2 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • FirstClass
Price was $1,115, price is now $852 per person
$852
per person
found 1 day ago
Great location! Very clean and the staff were super friendly. We really enjoyed our stay!

Reviewed on Dec 14, 2025

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (2,790 reviews)

Apr 10 - Apr 12

2 night stay

Orlando (MCO) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Delta • Non-stop • FirstClass
Price was $1,166, price is now $905 per person
$905
per person
found 1 day ago
Beautiful room and great customer service

Reviewed on Feb 7, 2026

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More About Flying To Pawling from Orlando

Route Information for Flights from Orlando to Pawling

Origin Airport IATA Code
ORL
Destination Airport IATA Code
SWF
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Orlando to Pawling

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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.