$66 Cheap flights to Orange County

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Top places to visit in Orange County

A large dam with a reservoir, rocky cliffs, and a forested area in the background.
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Cheap flights to Orange County from $66 One Way, $135 Round Trip

$135 return flights and $66 one-way flights to Orange County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jan 8 - Sun, Jan 10
BOS
Boston
LEB
Lebanon
$135 Roundtrip, found 1 hour ago
$135
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Fri, Jan 8 from Boston to Lebanon, returning Sun, Jan 10, priced at $135 found 1 hour ago
Thu, Dec 24 - Fri, Jan 1
BOS
Boston
LEB
Lebanon
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Cape Air flight, departing Thu, Dec 24 from Boston to Lebanon, returning Fri, Jan 1, priced at $145 found 2 days ago
Fri, Jan 1 - Fri, Jan 1
BOS
Boston
RUT
Rutland
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Cape Air flight, departing Fri, Jan 1 from Boston to Rutland, returning Fri, Jan 1, priced at $154 found 1 day ago
Wed, Dec 9 - Thu, Dec 17
BOS
Boston
LEB
Lebanon
$155 Roundtrip, found 2 days ago
$155
Roundtrip
found 2 days ago
Select Cape Air flight, departing Wed, Dec 9 from Boston to Lebanon, returning Thu, Dec 17, priced at $155 found 2 days ago
Sat, Nov 7 - Fri, Nov 13
BOS
Boston
LEB
Lebanon
$158 Roundtrip, found 5 hours ago
$158
Roundtrip
found 5 hours ago
Select Cape Air flight, departing Sat, Nov 7 from Boston to Lebanon, returning Fri, Nov 13, priced at $158 found 5 hours ago
Wed, Feb 24 - Mon, Mar 1
BOS
Boston
RUT
Rutland
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Cape Air flight, departing Wed, Feb 24 from Boston to Rutland, returning Mon, Mar 1, priced at $160 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
JFKNorth ClarendonOctober 9 to October 11$683
DCAWest LebanonOctober 10 to October 12$881
ATLNorth ClarendonOctober 10 to October 15$885
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Orange County Accommodation Deals

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $107 total per night from Nov 1 to Nov 2
$107 total
Nov 1 - Nov 2
Total with taxes and fees
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture ...
9.4/10 Exceptional! (569 reviews)
"My family loved how clean was the room and how nice was the staff."

Reviewed on Oct 1, 2026

Opens in a new windowMy Place Hotel-Randolph VT
Woodwards White Mountain Resort, BW Signature Collection

Woodwards White Mountain Resort, BW Signature Collection

3 out of 5
527 US Route 3 Lincoln NH
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $97 total per night from Nov 1 to Nov 2
$97 total
Nov 1 - Nov 2
Total with taxes and fees
Stay at this hotel in Lincoln. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Opens in a new windowWoodwards White Mountain Resort, BW Signature Collection
Indian Head Resort

Indian Head Resort

3 out of 5
664 US Route 3 Lincoln NH
$75 nightly
The price is $81 total per night from Oct 29 to Oct 30
$81 total
Oct 29 - Oct 30
Total with taxes and fees
Book a stay at this family-friendly hotel in Lincoln. Enjoy free WiFi, free parking, and 2 hot tubs. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (1,001 reviews)
"Bartender Josh was very friendly, the view is outstanding and so is the location. The clam chowder was excellent! The rest of the buffet was very disappointing, especially for the price. The rooms are very outdated and rustic but not in a good way. I would recommend it to friends but would have to ..."

Reviewed on Oct 2, 2026

Opens in a new windowIndian Head Resort
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Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$206 nightly
The price is $226 total per night from Oct 30 to Oct 31
$226 total
Oct 30 - Oct 31
Total with taxes and fees
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowAlign Inn Vermont
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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Orange County

Are you in the mood for a cruise? Shop Orbitz today for cheap cruises and flights to Orange County. Our award-winning cruise site features exclusive offers, information for first-timers and top destinations and activities. Make discount domestic and international travel plans in an instant with cutting-edge mobile tools from Orbitz.

Top Pick

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Exclusive Offers

Register for Orbitz email updates and our cruise experts will notify you of bargain tickets on cruises as they’re posted. Install our free mobile apps on your iPad, iPhone or Android for easy booking and mobile-only savings on flights to Orange County. Visit www.Orbitz.com to learn more about these amazing benefits and our 110% Best Price Guarantee.

First-Timers

Are you and your family cruise newbies? Orbitz offers Cruising 101 and Cruise FAQ to answer any questions you may have. Book your cruise and air travel with Orbitz On the Go for greater savings on Orange County flights.

Ports and Play

Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to Orange County and Orange County flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

What is the best airport to fly to in Orange County?
There's one primary entrance point for this region — Lebanon Municipal Airport (LEB). Book your flights to this popular gateway and check out all that Orange County has to offer.
How much is a flight to Orange County?
Prices for round-trip flights to Orange County this past week fluctuated from $135 to $885. If you were flying one-way from Boston (BOS), you could have scored prices from just $66.
How to book the cheapest flight to Orange County?
With Orbitz, you'll find some of the most exciting flight deals around from a wide selection of airlines. But if you'd like to boost your prospects of picking up cheap flights to Orange County, here are a few pointers to consider:

  • Depending on where you're coming from, choose the 'Nearby airports' function (located under the departure and arrival options). Occasionally, alternative departure points will offer better prices on fares.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' link. You'll see the flight deals for the days around your selected departure. Ticket prices often vary depending on what day of the week it is.
  • You can also select the 'Show options' function to filter results for your preferred airline, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even choose the time of day you'd like to fly.
  • The early bird catches the most rewarding deals, so book as soon as you know your travel dates. The most affordable airfares sell fast and prices normally rise as the departure date gets closer.
  • Bundle your hotels, flights and car rentals into a package deal and score great discounts. Save your cash for things that really excite you, like exploring every corner of Orange County.
  • If practical, avoid flying during the busy season. Airfares are often at their most expensive during summer, school breaks and around other vacation times like Easter and Thanksgiving.

What is the best time to book a flight to Orange County?
Generally speaking, January is the best time to purchase your airfare. This is closely followed by February and August. Bear this in mind while searching for a cheap flight to Orange County.
What day of the week is the cheapest to book a flight to Orange County?
If you're after cheap airfares to Orange County, the best days to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to Orange County?
According to Orbitz data from 2020, Monday is normally the best day for cheap flights to Orange County. Tuesday also has wallet-friendly fares, whereas Saturday has the highest ticket rates. Although flying out at the weekend may be more convenient, you'll have more cash in your pocket to play with if you set off earlier in the week.
What is the cheapest month to fly to Orange County?
Get set to jet for less in August. This is generally an excellent month to take off if you're after cheap flights to Orange County, according to Orbitz data. The most expensive time to take off is June, so avoid this month if possible.
Which airlines allow free cancellation?
If you think your travel plans could change, Orbitz will help you find a flexible ticket. All you have to do is click on "Filter by flexible change policies" when searching for your Orange County flights. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — in addition to our awesome low prices.
What do I need for the flight to Orange County?
From onboard entertainment to travel basics like noise-canceling headphones, there are a number of things a regular flyer won't take off without. To ensure you're prepared for your trip, have a read through this useful list:

  • Travel paperwork such as visas and some identification are essential. To avoid any unnecessary delays at check-in, make sure your booking is under the same name, birth date and gender as indicated on your current ID.
  • Pack your carry-on bag with activities and snacks and watch time whiz by on your medium-haul flight. If you get the chance, join the airport's Wi-Fi and transfer your favorite playlist or podcast to your phone prior to take off.
  • Together, air conditioning and high altitudes make for a cold environment. No matter what the season is in Orange County, pack a sweater to keep warm and cozy while on the plane.

How do I get cheap first-class/business deals to Orange County?
Smart travelers have a knack for finding business or first-class fares to Orange County without the astronomical price tag. Follow in their footsteps with these helpful tips:

  • Be flexible with your travel dates and hold out for sales on business or first-class airfares.
  • Many low-cost carriers nowadays offer excellent business-class seating without the pricey fees.
  • Bid for an upgrade in online auctions or upgrade your seat through your flight loyalty scheme.

What is the best time to go to Orange County?
Orange County is an excellent vacation destination year-round, but the most popular months are March, May and November. If you're into warmer weather, consider visiting in summer. Like most destinations in the Northern Hemisphere, the summer season begins June 20. At this time, temperatures normally float between 55 ºF and 75 ºF during the day.

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.