Flights To Orange County - Cheap Flights Starting at CA $111

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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.

Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $220 Roundtrip, found 3 days ago
CA $220
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Mon, Sep 14, priced at CA $220 found 3 days ago
Thu, Aug 27 - Sun, Aug 30
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $243 Roundtrip, found 3 days ago
CA $243
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to Stewart Intl., returning Sun, Aug 30, priced at CA $243 found 3 days ago
Tue, Sep 1 - Sun, Sep 6
MCO
Orlando Intl.
HPN
Westchester County
CA $257 Roundtrip, found 5 hours ago
CA $257
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Westchester County, returning Sun, Sep 6, priced at CA $257 found 5 hours ago
Thu, Oct 22 - Sun, Oct 25
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $259 Roundtrip, found 3 days ago
CA $259
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Oct 22 from Orlando Intl. to Stewart Intl., returning Sun, Oct 25, priced at CA $259 found 3 days ago
Thu, Sep 24 - Sat, Oct 3
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $265 Roundtrip, found 4 days ago
CA $265
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 24 from Orlando Intl. to Stewart Intl., returning Sat, Oct 3, priced at CA $265 found 4 days ago
Wed, Sep 30 - Fri, Oct 2
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $270 Roundtrip, found 1 day ago
CA $270
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Stewart Intl., returning Fri, Oct 2, priced at CA $270 found 1 day ago
Tue, Jul 21 - Sat, Jul 25
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $274 Roundtrip, found 2 days ago
CA $274
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Jul 21 from Orlando Intl. to Stewart Intl., returning Sat, Jul 25, priced at CA $274 found 2 days ago
Wed, Oct 21 - Sat, Oct 24
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $276 Roundtrip, found 1 day ago
CA $276
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 21 from Orlando Intl. to Stewart Intl., returning Sat, Oct 24, priced at CA $276 found 1 day ago
Tue, Sep 1 - Wed, Sep 9
YYC
Calgary Intl.
HPN
Westchester County
CA $531 Roundtrip, found 2 hours ago
CA $531
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Sep 1 from Calgary Intl. to Westchester County, returning Wed, Sep 9, priced at CA $531 found 2 hours ago
Sat, Sep 12 - Sat, Sep 19
YYZ
Pearson Intl.
HPN
Westchester County
CA $534 Roundtrip, found 3 days ago
CA $534
Roundtrip
found 3 days ago
Select WestJet flight, departing Sat, Sep 12 from Pearson Intl. to Westchester County, returning Sat, Sep 19, priced at CA $534 found 3 days ago
Tue, Sep 1 - Wed, Sep 9
YYC
Calgary Intl.
HPN
Westchester County
CA $661 Roundtrip, found 2 hours ago
CA $661
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Sep 1 from Calgary Intl. to Westchester County, returning Wed, Sep 9, priced at CA $661 found 2 hours ago
OriginDestinationTravel datesFlights from*
RDUNewburghAugust 26 to September 2CA $187
RDUWest HarrisonAugust 13 to August 16CA $199
MCONewburghSeptember 10 to September 14CA $220
MCOWest HarrisonSeptember 1 to September 6CA $257
TPAWest HarrisonSeptember 16 to September 22CA $337
FLLWest HarrisonJuly 25 to August 1CA $359
ORDWest HarrisonJuly 23 to July 26CA $577
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghJuly 11 to July 25CA $299
MCOWest HarrisonJuly 10 to July 12CA $545
TPAWest HarrisonJuly 12 to July 15CA $676
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Radio Hotel
4.0-star property

Radio Hotel

Aug 21 - Aug 28

7 night stay

Calgary (YYC) to New York (JFK)

American Airlines • Non-stop roundtrip • Coach
Price was CA $1,975, price is now CA $1,329 per person
CA $1,329
per person
found 17 hours ago
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Sep 24 - Sep 28

4 night stay

Halifax (YHZ) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • Coach
Price was CA $2,883, price is now CA $1,826 per person
CA $1,826
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Sep 24 - Sep 28

4 night stay

Halifax (YHZ) to Newark Liberty Intl. Airport (EWR)

American Airlines • Roundtrip • Coach
Price was CA $2,874, price is now CA $1,831 per person
CA $1,831
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! (1,007 reviews)
"Service was not provided on time"

Reviewed on Jul 7, 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! (1,068 reviews)
"We took our grandchildren to Legoland and chose this hotel for its proximity to the park, indoor pool and breakfast features. Well, it was 20 minutes away, which wasn’t as close as I thought. I thought I had read it was 9 minutes away but it must have been 9 miles, which took 20+ minutes. My mistake, ..."

Reviewed on Jul 7, 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! (1,006 reviews)
"the breakfast was great the staff is wonderful the rooms are nice and clean stay here all the time when we go to middle town even my fur baby loves then the pool and hot tub are nice and clean excellent hotel."

Reviewed on Jul 7, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Middletown-Goshen
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Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a nightclub. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
4.8/10 (1,011 reviews)
"Like a unclean prison, unsafe crime at night pounding on doors 2am, almost decided to sleep in car"

Reviewed on Jul 6, 2026

Opens in a new windowRamada by Wyndham Newburgh/West Point
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 $187. 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 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 CA $187. 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 $187 and CA $676 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.