$43 Cheap Flights to Shelter Island, NY

Flights to Shelter Island at a glance

Traveling to Shelter Island is easy, with budget airlines providing numerous flight options. Assess flight schedules and journey times to find the cheapest flight to Shelter Island that aligns with your budget and itinerary as you prepare to explore the city’s renowned attractions and neighborhoods.

• Major airport near Shelter Island: Tweed - New Haven Regional Airport (HVN)
• Flights per week: 180+ flights arriving at Shelter Island airport
• Number of airlines that fly to Shelter Island: around 2 carriers

Popular airport near Shelter Island

Shelter Island is a charming destination perfect for outdoor adventures, romantic getaways, and beach vacations. With its appealing mix of family-friendly activities and entertainment, it's no wonder that travelers seek out this lovely city. The closest airport serving Shelter Island is the East Hampton Airport, providing convenient domestic flights for visitors.

• Tweed - New Haven Regional Airport (HVN): Situated in New Haven County, Connecticut, approximately 32 miles from Shelter Island, this airport operates both domestic and international flights. It connects to about 25 domestic cities and one international destination. Breeze and Avelo Airlines are among the popular carriers servicing this location.

Top routes to Shelter Island

• Orlando (MCO) to Shelter Island (HVN), with one-way flights starting at around $40
• Raleigh (RDU) to Shelter Island (HVN), with one-way airfare from around $35
• West Palm Beach (PBI) to Shelter Island (HVN), with one-way tickets available from around $40
• Charleston (CHS) to Shelter Island (HVN), with one-way fares starting at around $30
• Tampa (TPA) to Shelter Island (HVN), with one-way flight options from around $50

Cheapest routes to Shelter Island

• Baltimore (BWI) to Shelter Island (HVN), with cheap one-way fares from around $30
• Norfolk (ORF) to Shelter Island (HVN), with affordable one-way prices from around $30
• Charleston (CHS) to Shelter Island (HVN), with budget one-way fares from around $30
• Richmond (RIC) to Shelter Island (HVN), with affordable one-way prices from around $35
• Raleigh (RDU) to Shelter Island (HVN), with low one-way fares from around $35

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

Top airlines with flights to Shelter Island

• Breeze: Operating flights to Tweed - New Haven Regional Airport (HVN), Breeze represents about 54% of the arrivals to Shelter Island. Expect an average one-way fare of around $90.
• Avelo Airlines: Also flying into Tweed - New Haven Regional Airport (HVN), Avelo Airlines makes up roughly 46% of arrivals to Shelter Island, with average one-way fares near $100.

Best time to fly to Shelter Island

The most popular months for travelers to fly to Shelter Island are March, April, and June, when peak temperatures in Shelter Island can reach up to 64.9°F in June. If you prefer quieter travel, consider September, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 68.2°F. For better deals, August usually offers the lowest average one-way fare around $85, roughly 15% cheaper than the yearly average. Looking for additional cheaper months to fly? October, September, and May offer average one-way fares of around $89, making them good options for flexible travelers.

*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 Shelter Island

Getting some of the best deals on flights to Shelter Island 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 Shelter Island 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 Shelter Island flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Shelter Island

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

• Public transportation: From Tweed - New Haven Regional Airport, New Haven Seaport, a seaport, is located about 1.3 miles away by car, while New Haven State Street Station, a train station, is approximately 3.5 miles from the airport, also most conveniently accessed by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Shelter Island, with private rides that can be arranged in advance.
• Car rental: Renting a car in Shelter Island is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Shelter Island 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 Shelter Island

• Sag Harbor: Sag Harbor is located 5 miles drive away from Shelter Island and is a charming city known for its blend of outdoor activities and romantic spots. Visitors can enjoy the picturesque Sag Harbor Marine Park, ideal for a beach vacation, or relax at East Hampton Main Beach. For those interested in culture, the Sag Harbor Whaling and Historical Museum offers a glimpse into local history. Whether you're looking to hit the golf course or spend a day at the beach, Sag Harbor has something for everyone.
• Greenport: Greenport is located 3 miles drive away from Shelter Island and offers a delightful escape for couples and outdoor enthusiasts alike. With beautiful beaches like 67 Steps Beach and family-friendly spots such as Orient Point County Park, it's perfect for a leisurely day out. The Railroad Museum of Long Island provides a fascinating cultural experience. Enjoy the vibrant atmosphere, especially during the warmer months when the town comes alive with music concerts and recreational activities.
• Wainscott: Wainscott is located 11 miles drive away from Shelter Island and is a scenic destination that appeals to those seeking outdoor adventures and romantic getaways. The area boasts beautiful beaches, including East Hampton Main Beach, and lush parks. Visitors can explore The Jewish Center of the Hamptons for a cultural experience or wander through the stunning LongHouse Reserve, a sculpture garden perfect for families and nature lovers. Wainscott is especially inviting in the summer, making it a great spot for relaxation and exploration.

Tips for short-haul flights to Shelter Island

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

• Pack light and skip checked bags—with budget airlines, traveling with just a carry-on is often the most economical choice. Maximize your space by using mini toiletries, wearing your heaviest clothing, and coordinating your outfits. This strategy also helps you dodge 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 ahead of time, 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 before departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack your favorite snacks and a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Shelter Island

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

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow free seat selection once online check-in opens, typically 24–48 hours prior to your flight. Some airlines may permit seat selection even earlier.
• Arrive at the airport in plenty of time—aim to be at the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you have some extra time, take the opportunity to explore the shops, grab a coffee, or unwind at the 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—begin synchronizing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Try to either sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Tips to find the cheapest flights to Shelter Island

The cheapest day to fly

Get started finding a cheap flight to Shelter Island on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

October is the cheapest month to fly to Shelter Island. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Shelter Island. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Shelter Island, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Shelter Island

The lowest price for round-trip flights to Shelter Island in 2026 starts from $86, while one-way tickets start from from $43. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Shelter Island. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Shelter Island

Allegiant Air, Frontier Airlines, Southwest Airlines, American Airlines, United, Delta are just some of the airlines that can typically offer cheap tickets to Shelter Island. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Shelter Island and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Shelter Island, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Shelter Island. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Shelter Island plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Shelter Island

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Shelter Island.

Stopover savings

The cheapest tickets to Shelter Island are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Shelter Island. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Shelter Island for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Shelter Island. Simply download the free Expedia app to your smart device and activate Shelter Island flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Shelter Island. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.