Cheap Flights to Orange County from $41 (2026/2027)

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Sunrise image of the Arrigoni Bridge in Middletown, CT

Middletown

Flights
Middletown

How Much Does it Cost To Fly To Orange County?

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

Sat, Sep 19 - Fri, Sep 25
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$82 Roundtrip, found 14 hours ago
$82
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Sep 19 from Raleigh - Durham Intl. to Westchester County, returning Fri, Sep 25, priced at $82 found 14 hours ago
Sat, Sep 19 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Sep 19 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $87 found 4 days ago
Sat, Sep 19 - Sat, Sep 26
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$92 Roundtrip, found 4 days ago
$92
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Sep 19 from Raleigh - Durham Intl. to Westchester County, returning Sat, Sep 26, priced at $92 found 4 days ago
Wed, Jun 10 - Tue, Sep 1
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$94 Roundtrip, found 5 days ago
$94
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 10 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 1, priced at $94 found 5 days ago
Sat, Sep 5 - Tue, Sep 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$97 Roundtrip, found 18 hours ago
$97
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 8, priced at $97 found 18 hours ago
Sat, Sep 19 - Wed, Sep 23
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 13 hours ago
$102
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Sep 19 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Sep 23, priced at $102 found 13 hours ago
Fri, Feb 26 - Wed, Mar 10
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$107 Roundtrip, found 5 hours ago
$107
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Fri, Feb 26 from Raleigh - Durham Intl. to Westchester County, returning Wed, Mar 10, priced at $107 found 5 hours ago
Wed, Nov 11 - Sun, Nov 22
RDU
Raleigh - Durham Intl.
HPN
Westchester County
$112 Roundtrip, found 13 hours ago
$112
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Wed, Nov 11 from Raleigh - Durham Intl. to Westchester County, returning Sun, Nov 22, priced at $112 found 13 hours ago
Wed, Sep 9 - Sat, Sep 12
TPA
Tampa Intl.
SWF
Stewart Intl.
$156 Roundtrip, found 5 days ago
$156
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Sep 9 from Tampa Intl. to Stewart Intl., returning Sat, Sep 12, priced at $156 found 5 days ago
OriginDestinationTravel DatesFlights From*
RDUWest HarrisonAugust 26 to August 31$97
RDUNewburghSeptember 5 to September 9$102
MCONewburghSeptember 3 to September 6$122
MCOWest HarrisonAugust 25 to September 1$144
TPANewburghSeptember 5 to September 12$157
TPAWest HarrisonAugust 25 to August 31$173
FLLWest HarrisonJuly 21 to July 29$217
JFKWest HarrisonJune 11 to June 17$287
ATLWest HarrisonJune 30 to July 5$295
CLTWest HarrisonJune 16 to June 22$335
ORDWest HarrisonJune 16 to June 23$336
DENWest HarrisonJune 16 to June 20$337
MIAWest HarrisonJune 10 to June 19$399
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCONewburghMay 29 to June 6$173
RDUNewburghMay 30 to June 6$224
TPANewburghMay 30 to June 6$357
MCOWest HarrisonMay 30 to June 6$367
ATLWest HarrisonMay 29 to June 5$378
FLLWest HarrisonMay 30 to June 7$400
RDUWest HarrisonMay 31 to June 6$413
ORDWest HarrisonMay 29 to May 30$434
TPAWest HarrisonMay 30 to June 7$446
EKWWest HarrisonMay 29 to June 1$648
JFKWest HarrisonMay 29 to May 31$821
*Prices include taxes and fees

Best Orange County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis
4.5-star property

New York Marriott Marquis

Jul 2 - Jul 6

4 night stay

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

Frontier Airlines • Coach

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

JetBlue Airways • Coach
Price was $1,705, price is now $887 per person
$887
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Aug 11 - Aug 18

7 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $1,921, price is now $1,027 per person
$1,027
per person
found 1 day ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Aug 11 - Aug 18

7 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,734, price is now $934 per person
$934
per person
found 1 day ago
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Travelers ❤️ These Orange County 🏨

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
8.4/10 Very Good! (1,004 reviews)
"The cabin we stayed it was unique, but lots of walking from your car on a slanted walkway. Shared den and the room smelled heavily of smoke from the inner fireplace. Small room and tiny old bathroom. Not what we were expecting from the pictures. Received an odd email about checkin but nothing told ..."

Reviewed on May 25, 2026

Opens in a new windowOverlook Lodge at Bear Mountain
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Orange County Community College and Paramount Theatre are located nearby.
8.8/10 Excellent! (1,018 reviews)
"Everything was clean, comfortable and in working order."

Reviewed on May 19, 2026

Opens in a new windowSleep Inn & Suites Middletown - Goshen
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
9.4/10 Exceptional! (1,003 reviews)
"Great value for the money ☺️☺️"

Reviewed on May 25, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Middletown-Goshen
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Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

2.5 out of 5
1 Sleep Way Monroe NY
Book a stay at this business-friendly hotel in Monroe. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Woodbury Common Premium Outlets and Museum Village are located nearby.
9.4/10 Exceptional! (1,083 reviews)
"Nothing really unique so to say, breakfast was good, the staff was very nice especially Leigh (or Lee) I didn’t catch the spelling of her name. We didn’t use anything else but the room and had breakfast. Leigh at the front seat helped with questions and seemed very sincere. Appreciated her a ..."

Reviewed on May 26, 2026

Opens in a new windowSleep Inn & Suites Monroe - Woodbury
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much is the cheapest flight to Orange County?
The next trip you take doesn't have to make a huge dent in your finances. In the last seven days, the cheapest roundtrip flight to Orange County cost $82. Find the best deal and spend the dollars you save on exciting experiences. This price was available on Travelocity for flights to Orange County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Orange County?
There are 16 airlines that can take you to Orange County. If you're thinking about a journey to Newburgh, consider Allegiant Air. This popular carrier operates roughly 26 services a month to Orange County's main city.
What is the cheapest month to fly to Orange County?
Splurge more money on epic adventures rather than airfares by hopping on a plane to Orange County in September. This is the cheapest time to set off to this destination according to Travelocity's direct return flight demand from January to December last year. Take a look at our list of flights and get out of town on the cheap.
How can I check my flight status to Orange County?
Whether you'd like to check the status of your flight to Orange County or change your itinerary, you'll find all the important details on our handy portal, Trips. Click on "Trips" at the top right of our homepage, then log in or create a new account. Another simple way to manage and view your booking is with the Travelocity app. Get real-time advice like flight status alerts and quickly share updates with any family flying with you.
How do I find the best deals on flights to Orange County?
Be flexible with your travel dates and you're likely to find an amazing deal. After you've searched for flights on Travelocity, click the "Flexible dates" box above your results to compare prices with nearby days. Also try to book ahead of time and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Orange County was $82. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Orange County with Travelocity?
Where to start! With cheap flights to Orange County, rental cars and activities, you'll discover everything you need for the perfect getaway with Travelocity. Lock in your cheap family flights and make use of our round-the-clock social media support and Price Match Guarantee if necessary. Our goal is to offer stress-free travel every time you book with us so that you can spend less time on the nitty-gritty and more time having fun with your family and friends.
What are the most popular flight routes to Orange County?
With superb connections, organizing flights to Orange County is a cinch. Here are some of the most sought-after flight routes to this favorite destination:

  • Myrtle Beach, SC (MYR-Myrtle Beach Intl.) to Stewart Intl. Airport (SWF) - 17 flights a month.
  • St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.) to Stewart Intl. Airport (SWF) - 8 flights a month.
  • Savannah, GA (SAV-Savannah - Hilton Head Intl.) to Stewart Intl. Airport (SWF) - 8 flights a month.

How much is a flight to Orange County on average?
Passengers have found roundtrip flights to Orange County for between $82 and $821 with Travelocity in the last seven days. Whether you'd like to fly economy or business class, we'll help you find the best deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Orange County?
Browse through these popular routes for an idea of how long you'll be in your seat during a direct flight to Orange County:

  • Myrtle Beach, SC (MYR-Myrtle Beach Intl.) to Stewart Intl. Airport (SWF) - 1 hour and 50 minutes
  • St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.) to Stewart Intl. Airport (SWF) - 2 hours and 45 minutes
  • Savannah, GA (SAV-Savannah - Hilton Head Intl.) to Stewart Intl. Airport (SWF) - 1 hour and 57 minutes

What can I expect on a flight to Orange County?
That depends on several things. Is your flight to Orange County an hour long or many hours long? Have you booked with a full-service airline or a low-cost one? These things will affect the experience you have on board. If you're flying long haul, almost all airlines include drinks, food and entertainment. Low-cost carriers are a terrific option when it comes to cheap flights for family vacations or shorter trips. But, typically they won't have the same inclusions as a full-service airline.