Flights To Orange County - Cheap Flights Starting at CA $99

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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.

Fri, Jul 17 - Sun, Jul 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $222 Roundtrip, found 7 hours ago
CA $222
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Fri, Jul 17 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jul 19, priced at CA $222 found 7 hours ago
Sat, Jun 13 - Wed, Jun 17
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $223 Roundtrip, found 3 days ago
CA $223
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Jun 13 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 17, priced at CA $223 found 3 days ago
Wed, May 27 - Sat, Jun 6
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $224 Roundtrip, found 4 days ago
CA $224
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 27 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Jun 6, priced at CA $224 found 4 days ago
Tue, Jun 16 - Fri, Jun 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $236 Roundtrip, found 3 days ago
CA $236
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Jun 16 from Raleigh - Durham Intl. to Westchester County, returning Fri, Jun 19, priced at CA $236 found 3 days ago
Sat, Jun 20 - Wed, Jun 24
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $244 Roundtrip, found 4 days ago
CA $244
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jun 20 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jun 24, priced at CA $244 found 4 days ago
Wed, Jul 1 - Sat, Jul 4
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $252 Roundtrip, found 3 days ago
CA $252
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Wed, Jul 1 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Jul 4, priced at CA $252 found 3 days ago
Fri, Jul 17 - Mon, Jul 20
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $253 Roundtrip, found 7 hours ago
CA $253
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Fri, Jul 17 from Raleigh - Durham Intl. to Westchester County, returning Mon, Jul 20, priced at CA $253 found 7 hours ago
Wed, Jun 17 - Tue, Jun 23
PBI
Palm Beach Intl.
HPN
Westchester County
CA $263 Roundtrip, found 6 days ago
CA $263
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jun 17 from Palm Beach Intl. to Westchester County, returning Tue, Jun 23, priced at CA $263 found 6 days ago
Mon, Jun 8 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $401 Roundtrip, found 13 hours ago
CA $401
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Jun 8 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $401 found 13 hours ago
Mon, Jun 8 - Sat, Jun 13
YYZ
Pearson Intl.
HPN
Westchester County
CA $479 Roundtrip, found 13 hours ago
CA $479
Roundtrip
found 13 hours ago
Select Delta flight, departing Mon, Jun 8 from Pearson Intl. to Westchester County, returning Sat, Jun 13, priced at CA $479 found 13 hours ago
Mon, Jul 20 - Mon, Jul 27
YYZ
Pearson Intl.
HPN
Westchester County
CA $510 Roundtrip, found 2 days ago
CA $510
Roundtrip
found 2 days ago
Select WestJet flight, departing Mon, Jul 20 from Pearson Intl. to Westchester County, returning Mon, Jul 27, priced at CA $510 found 2 days ago
OriginDestinationTravel datesFlights from*
MCOWest HarrisonJuly 29 to August 1CA $214
RDUWest HarrisonJuly 17 to July 19CA $222
RDUNewburghJune 13 to June 17CA $223
MCONewburghJune 11 to June 13CA $237
TPANewburghJune 10 to June 13CA $291
TPAWest HarrisonAugust 14 to August 17CA $304
FLLWest HarrisonJune 16 to June 22CA $327
LGAWest HarrisonJune 16 to June 18CA $672
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghMay 29 to May 31CA $262
TPAWest HarrisonMay 29 to June 1CA $583
FLLWest HarrisonMay 31 to June 1CA $911
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Jul 10 - Jul 13

3 night stay

Toronto (YYZ) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $4,582, price is now CA $2,707 per person
CA $2,707
per person
found 1 day ago
Luxury NY Home 3BR with Easy Parking
3.0-star property

Luxury NY Home 3BR with Easy Parking

Jul 21 - Jul 25

4 night stay

Toronto (YYZ) to White Plains (HPN)

Porter Airlines • Roundtrip • Coach
Price was CA $5,295, price is now CA $3,327 per person
CA $3,327
per person
found 8 hours ago
3BR Prime Luxury near NYC w Arcade Room
2.0-star property

3BR Prime Luxury near NYC w Arcade Room

Jul 21 - Jul 25

4 night stay

Toronto (YYZ) to White Plains (HPN)

Porter Airlines • Roundtrip • Coach
Price was CA $6,167, price is now CA $3,901 per person
CA $3,901
per person
found 8 hours 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! (1,003 reviews)
"VERY small bathroom. Temperature control is in a shared area and not room specific."

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! (1,017 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! (1,002 reviews)
"The rooms were clean and a nice smell in the hallways."

Reviewed on May 24, 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! (1,081 reviews)
"The room was pristine, breakfast great, ample and easy parking, very warm staff!"

Reviewed on May 22, 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 CA $214. 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 20 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 July. 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 CA $214. 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 CA $214 and CA $911 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.