$48 Cheap Flights to Southold, NY

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Flights to Southold at a glance

Flying to Southold is easy, thanks to budget airlines that provide a range of flight options. Review the travel times and choose the flight that best aligns with your budget and schedule while you discover the city’s renowned attractions and neighborhoods.

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

Popular airport near Southold

Southold is a charming city perfect for outdoor enthusiasts, romantic getaways, and entertainment-filled vacations. Visitors flock to Southold for its beautiful beaches, family-friendly activities, and vibrant atmosphere. The city is conveniently accessible via a major airport, making travel easy for everyone.

• Tweed - New Haven Regional Airport (HVN): Situated in New Haven County, Connecticut, approximately 28 miles from Southold, this airport provides access to both domestic and international flights, linking travelers to around 25 domestic cities and 1 international destination. Breeze and Avelo Airlines are among the prominent carriers operating here.

Top routes to Southold

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

Cheapest routes to Southold

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

• Breeze: Operates flights to Tweed - New Haven Regional Airport (HVN), providing approximately 54% of arrivals to Southold. Expect to pay around $90 for an average one-way ticket.
• Avelo Airlines: Serves Tweed - New Haven Regional Airport (HVN), accounting for about 46% of arrivals in Southold. The typical one-way fare is roughly $100.

Best time to fly to Southold

The most popular months for travelers to fly to Southold are March, April, and June, when peak temperatures in Southold 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 Southold

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

*For members. Select hotels.

Arriving in Southold

Southold welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Southold 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 situated approximately 3.5 miles from the airport, also accessible by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Southold, with private rides that can be arranged in advance.
• Car rental: Renting a car in Southold is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Southold 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 Southold

• Sag Harbor: Sag Harbor is located 12 miles drive away from Southold and offers a captivating combination of outdoor adventures and romantic beach experiences. This charming city is home to popular attractions like the Sag Harbor Marine Park, perfect for those seeking adventure on the water, and the historic Sag Harbor Whaling and Historical Museum, which provides a glimpse into the area's maritime past. Visitors can unwind on the beautiful East Hampton Main Beach or enjoy a round of golf at one of the local courses, making Sag Harbor a delightful getaway for all kinds of travelers.
• Greenport: Greenport is located 4 miles drive away from Southold and is a vibrant destination that enchants visitors with its outdoor activities and beachside romance. Known for its scenic 67 Steps Beach, Greenport offers a perfect spot to soak up the sun and enjoy the ocean. The Orient Point County Park provides a wonderful recreational area for families, while the Railroad Museum of Long Island allows culture enthusiasts to delve into the area’s rail history. With its charming atmosphere, Greenport is an ideal stop for those seeking relaxation and exploration.
• Shelter Island: Shelter Island is located 5 miles drive away from Southold, where travelers can immerse themselves in a serene and romantic beach environment. The island features the Gardiner's Bay Country Club, ideal for golf enthusiasts, and the pristine East Hampton Main Beach for sunbathers looking to relax by the shore. The Shelter Island Historical Society offers a deeper understanding of the local heritage, making it a worthwhile visit. With its tranquil setting and outdoor activities, Shelter Island is a perfect escape for those looking to unwind and reconnect with nature.

Tips for short-haul flights to Southold

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 more economical. Maximize space by using mini toiletries, wearing your bulkiest clothing, and planning your outfits strategically. This also allows you to bypass the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may not provide in-flight entertainment. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself entertained. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, aim to get to the airport at least 1.5 to 2 hours before departure, taking into account potential traffic and security lines.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while at the airport.

Tips for long-haul flights to Southold

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

• Select your seat in advance—for longer flights, choosing your seat is crucial for comfort. Full-service airlines often provide complimentary seat selection once online check-in begins, typically 24–48 hours prior to your flight. Some airlines allow you to select your seat even earlier than this.
• Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security screening, and immigration procedures.
• Relax at the airport—if you find yourself with 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 to align your body clock by changing your watch and sleep patterns to correspond with your destination's time zone. Try to sleep or stay awake during the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Southold

The cheapest day to fly

Get started finding a cheap flight to Southold 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

February is the cheapest month to fly to Southold. 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 Southold. 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 Southold, 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 Southold

The lowest price for round-trip flights to Southold in 2026 starts from $94, while one-way tickets start from from $48. 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 Southold. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Southold

Frontier Airlines, Allegiant Air, JetBlue Airways, Southwest Airlines, Delta, United, American Airlines are just some of the airlines that can typically offer cheap tickets to Southold. 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 Southold and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Southold, 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 Southold. 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 Southold 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 Southold

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 Southold.

Stopover savings

The cheapest tickets to Southold are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Southold. 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 Southold 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 Southold. Simply download the free Expedia app to your smart device and activate Southold 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 Southold. 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.

Frequently Asked Questions

What month is the cheapest to fly to Southold?

February is the cheapest month to travel to Southold. Demand is lower then, so fares are generally more affordable. Booking your trip outside of public holidays and school breaks could also help you save.

Which US cities have the cheapest flights to Southold?

Los Angeles, San Francisco and Boston generally have cheap flights to Southold. Remember that fares may vary based on factors like demand, number of stopovers and time of year.

Which US cities fly direct to Southold?

You can fly to Southold without any stops from 58 US destinations. To find a nonstop journey, select "Direct flights only" when searching for flights to Southold on Expedia. Then, explore the options and find the best departure out of any of these cities:

• Los Angeles
• San Francisco
• Boston
• Miami
• Orlando

How to find a cheap flight to Southold?

To snag cheap flights to Southold, book ahead of time and travel during the low season. Want a handy tip? Fly on a Thursday and you'll save 16% on average compared to those who travel on a Sunday.* Sign up for price tracking on the Expedia app and we'll let you know the moment prices 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 Southold?

Although booking in advance is generally the best way to save cash, don't worry if your Southold vacation is last minute. You can still get cheap flights to Southold, especially if your plans have some flexibility. Try changing your travel dates, looking at different ticket types or jetting out of another airport.

How far in advance should I book a flight to Southold?

Secure the travel dates you want and a fare that suits your budget by booking your domestic flight to Southold up to 28 days in advance. Search for tickets two to four months ahead if you're visiting Southold from an international destination.*

*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 Southold?

You'll save an average of 8% by buying tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to getting a cheap flight to Southold, it's all about timing.

*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 Southold?

Find your passport, pack your bags and choose from these quality airlines that fly to Southold:

• Delta Air Lines - 12,611 flights to Southold each month, including 6,687 flights to LaGuardia Airport (LGA) per month.
• United Airlines - 10,219 flights to Southold each month, including 9,000 flights to Liberty Intl. Airport (EWR) per month.
• American Airlines - 6,599 flights to Southold each month, including 3,362 flights to LaGuardia Airport (LGA) per month.

Where do you fly into Southold?

When flying to Southold, the main airport to touch down at is Tweed - New Haven Regional Airport (HVN). You can also head to nearby hubs like MacArthur Airport (ISP), Hartford, CT (HFD-Hartford - Brainard) or Bradley Intl. Airport (BDL). Another great option to keep in mind when you fly to Southold is East Hampton, NY (HTO).

Can I save money by booking a Southold trip package?

Bundle your hotel and flight and you could save hundreds of dollars. Better yet, you can add extras like car rentals and tours to your Southold flight and hotel package deal. With Expedia, it's simple to look after all your Southold travel arrangements in the same place.

Can I change or cancel my flight to Southold?

You can often cancel or change your flight to Southold within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may be issued a credit toward a future flight rather than a direct refund. It's important to check the airline's terms of service in your itinerary for specific details. You can use Expedia's "No cancel fee" or "Changes included" filters during your search to find cheap flights to Southold with flexible change policies. For additional information, head to our Customer Service Portal.