Cheap Flights to Highland, NY

Popular airlines to Highland

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What you need to know for your flight to Highland

Flights to Highland at a glance

Traveling to Highland is easy—simply choose between full-service and low-cost airlines. Compare flight schedules and journey times to find a direct flight that fits your budget and travel plans, allowing you to explore the city’s renowned sights and vibrant neighborhoods.

  • Major airport near Highland: Stewart International Airport (SWF)
  • Flights per week: 49 flights arriving at Highland airport
  • Number of airlines that fly to Highland: around 2 carriers

Popular airport near Highland

Highland is a charming city perfect for outdoor enthusiasts, adventure seekers, and those looking to enjoy stunning scenery. Visitors are drawn here for family getaways, romantic escapes, and cultural experiences. Conveniently, the nearest airport to Highland is Stewart Airport, along with other major airports serving the area.

  • Stewart International Airport (SWF): Situated in Orange County, New York, approximately 17 miles from Highland, this airport offers a mix of domestic and international flights, connecting to around 4 cities within the U.S. and 3 international locations. Breeze and Fly Play are among the notable airlines serving this hub.

Top routes to Highland

  • Orlando (MCO) to Highland (SWF), with one-way flights starting at around $60
  • Charleston (CHS) to Highland (SWF), with one-way flight options from around $50
  • Reykjavik (KEF) to Highland (SWF), with one-way tickets available from around $130
  • Fort Myers (RSW) to Highland (SWF), with one-way airfare from around $50
  • Vero Beach (VRB) to Highland (SWF), with one-way flight options from around $60

Cheapest routes to Highland

  • Charleston (CHS) to Highland (SWF), with low-cost one-way tickets from around $50
  • Fort Myers (RSW) to Highland (SWF), with cheap one-way fares from around $50
  • Orlando (MCO) to Highland (SWF), with low-cost one-way tickets from around $60
  • Vero Beach (VRB) to Highland (SWF), with affordable one-way prices from around $60
  • Reykjavik (KEF) to Highland (SWF), with low-cost one-way tickets from around $130

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Highland

  • Breeze: Operating flights to Stewart International Airport (SWF), Breeze represents about 84% of incoming traffic to Highland. The typical one-way fare hovers around $110.
  • Fly Play: Also serving Stewart International Airport (SWF), Fly Play makes up roughly 16% of arrivals to Highland. Travelers can expect average one-way fares to be about $420.

Best time to fly to Highland

The most popular months for travelers to fly to Highland are January, March, and July, when peak temperatures in Highland can reach up to 73.2°F in July. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 64°F and typically the lowest average one-way fare (around $103), roughly 30% cheaper than the yearly average.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January26.8°F (-2.9°C)Light RainMostly SunnyHigh$144
February28.6°F (-1.9°C)Light RainMostly SunnyAverage$143
March36.3°F (2.4°C)Light RainMostly SunnyHigh$150
April48.0°F (8.9°C)Light RainMostly SunnyAverage$168
May59.2°F (15.1°C)Light RainMostly SunnyAverage$139
June67.1°F (19.5°C)Light RainMostly SunnyAverage$141
July73.2°F (22.9°C)Light RainMostly SunnyHigh$191
August71.1°F (21.7°C)Light RainMostly SunnyAverage$188
September64.0°F (17.8°C)Light RainMostly SunnyLow$103
October52.9°F (11.6°C)Light RainMostly SunnyLow$127
November40.6°F (4.8°C)Light RainMostly SunnyLow$141
December32.7°F (0.4°C)Light RainMostly SunnyAverage$151

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Highland

Getting some of the best deals on flights to Highland is all about timing and flexibility. Here are some key tips to help you save:

  1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
  2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
  3. Bundle and save—book a flight and unlock a hotel deal on Expedia*, or explore our Highland hotel and flight deals.
  4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
  5. Earn miles—you can earn airline miles when you book your Highland flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Highland

Highland welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Highland efficiently:

  • Public transportation: From Stewart International Airport, Pollepel Island Seaport, a seaport, is about 5.9 miles away, providing convenient access to the waterfront for travelers.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Highland, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Highland is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Highland on Expedia.
  • Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Highland

  • Poughkeepsie Waterfront: Located 2 miles drive away from Highland, Poughkeepsie Waterfront offers a delightful blend of outdoor activities and cultural experiences. Visitors can enjoy scenic views along the waterfront while exploring attractions like Vassar College and the Culinary Institute of America, both esteemed educational institutions. The Mid-Hudson Civic Center hosts various events, making this area a hub of family-friendly activities and culture. Whether you're looking to stroll by the lake or engage in local events, Poughkeepsie Waterfront is a great spot to experience the picturesque beauty of the Hudson River.
  • Clintondale: Clintondale is located 5 miles drive away from Highland and is perfect for travelers seeking adventure and outdoor fun. With access to national state parks and nature reserves, this city is a haven for nature enthusiasts. Don’t miss the chance to visit Mohonk Lake, which offers stunning views and recreational opportunities. Clintondale also features shopping centers where visitors can enjoy a leisurely day out. With its combination of natural beauty and urban conveniences, Clintondale is an excellent destination for families and outdoor lovers alike.
  • Rosendale: Rosendale is located 11 miles drive away from Highland and is an ideal destination for those who appreciate beautiful scenery and outdoor activities. The city boasts access to ski fields and recreational areas, making it a great winter getaway as well as a summer retreat. Explore the natural splendor of Mohonk Lake or hike in the surrounding mountains. The Culinary Institute of America and the State University of New York-New Paltz add a cultural touch to your visit. With its mix of adventure and scenic beauty, Rosendale is perfect for nature lovers year-round.

Tips for short-haul flights to Highland

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

  • Pack light and skip checked bags—when flying with budget airlines, traveling with just a carry-on is often more economical. Maximize your packing efficiency by using travel-sized toiletries, donning your bulkiest clothing, and coordinating outfits ahead of time. This approach also helps you bypass the wait at baggage claim upon arrival.
  • Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself occupied, download TV shows, movies, music, or podcasts in advance, and consider bringing a book. Remember to charge your devices fully before you board.
  • Arrive at the airport in plenty of time—even for short or domestic flights, it's advisable to arrive at least 1.5 to 2 hours prior to departure, allowing for potential traffic and security delays.
  • Bring your own snacks and water—pack your own snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Highland

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

  • Select your seat in advance—for longer flights, choosing your seat can significantly enhance your comfort. Full-service airlines often provide free seat selection once online check-in opens, typically 24–48 hours prior to your flight. Some airlines allow seat selection even earlier.
  • Arrive at the airport in plenty of time—make sure to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
  • Relax at the airport—if you find yourself with extra time, take the opportunity to explore the shops, visit a coffee shop, or unwind at your gate or in a departure lounge if you have access. Airport Wi-Fi is generally free and available.
  • Adjust to the new time zone mid-flight—start acclimating your body clock by setting your watch and modifying your sleep schedule to align with your destination's time zone. Aim to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Frequently asked questions

What month is the cheapest to fly to Highland?
Plan your trip for if you're looking for a deal on your fare. It's the cheapest month to fly to Highland. Try to avoid traveling during peak periods such as major public holidays or events.
Which US cities have the cheapest flights to Highland?
Orlando, Myrtle Beach and Charleston usually have cheap flights to Highland. Keep in mind that fares vary based on factors such as demand, holiday periods and number of stopovers.
Which US cities fly direct to Highland?
You can fly to Highland without stopovers from US cities like Orlando and Myrtle Beach. Just select "Direct flights only" when searching for flights to Highland on Expedia. Then, compare your options and choose the most suitable departure for your vacation.
How to find a cheap flight to Highland?
Book in advance or look for a cheap flight to Highland during the off-season, such as January and February. Flying off on a Thursday could also save you an average of 16% compared to a Sunday flight.* The Expedia app makes it even easier to know when to book. Just turn on the toggle for "Watch prices" and you'll get notified as soon as fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Highland?
Staying flexible with your plans may help you to find last-minute deals on cheap flights to Highland. To view all the available options, consider exploring different ticket types, tweaking your Highland trip dates, jetting out of an alternative airport or using another carrier.
How far in advance should I book a flight to Highland?
To pick up the best deals on domestic journeys, book your flight to Highland 28 days ahead of your travel dates. For international flights, it's two to four months in advance. This boosts your chances of locking in your preferred departure dates, times and seats.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Highland?
You can save an average of 8% if you buy plane tickets on a Sunday rather than Fridays, which tend to be the priciest day to book.* When it comes to getting a cheap flight to Highland, timing makes a difference.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Highland?
There are 7 carriers connecting Highland with 18 airports worldwide. The key point of arrival to this city is Westchester County Airport (HPN). Book a ticket with any of these leading airlines to Highland:

  • JetBlue Airways
  • Delta Air Lines
  • American Airlines
  • Cape Air

Where do you fly into Highland?
If you're flying to Highland, the main airport for arrivals is Stewart Intl. Airport (SWF). You can also jet into nearby hubs like Westchester County Airport (HPN), Dutchess County Airport (POU) or Montgomery, NY (MGJ-Orange County). Another possibility to think about when you fly to Highland is Danbury, CT (DXR-Danbury Municipal).
How far is the airport from central Highland?
You'll be roughly 17 mi southwest of the center of Highland after landing at Stewart Intl. Airport (SWF).
Can I save money by booking a Highland trip package?
It's possible to save hundreds of dollars if you secure a Highland flight and hotel package deal on Expedia. And you'll save yourself hassle by having all your travel arrangements in the same place. Try bundling your hotel and flight with extras such as car rentals and activities for your own personalized Highland trip.
Can I change or cancel my flight to Highland?
If you reserved your flight to Highland within the last 24 hours, you can usually change or cancel it without fees. After that, additional costs may apply depending on the airline's terms of service. To learn more, check out our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be issued a credit for future flights rather than a direct refund. When searching on Expedia, use the "No cancel fee" or "Changes included" boxes to compare tickets with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

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Travel information

Destination airport
Highland
Destination airport IATA code
POU

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