$105 Cheap Flights to Ossining, NY

Flights to Ossining at a glance

Traveling to Ossining is a breeze with a variety of options available. You can select from full-service or budget airlines, compare travel times, and choose the best flight that fits your budget and plans to discover the city's renowned attractions and neighborhoods.

• Major airports near Ossining: LaGuardia Airport (LGA), Westchester County Airport (HPN)
• Closest airport to Ossining: Westchester County Airport, HPN (around 10 miles)
• Flights per week: 6,350+ flights arriving across Ossining airports
• Number of airlines that fly to Ossining: around 25+ carriers

Popular airports near Ossining

Ossining is a charming city perfect for family outings, outdoor adventures, and urban getaways. Travelers flock to Ossining for its beautiful scenery and diverse activities. It’s conveniently accessible from two major airports, making it easy to plan your trip and explore all that this delightful destination has to offer.

• LaGuardia Airport (LGA): Situated in Queens County, New York, approximately 27 miles from Ossining, LaGuardia is a key airport offering both domestic and international flights. It connects travelers to over 235 domestic cities and 105 international destinations. Passengers can opt for enhanced comfort by selecting first class, premium economy, or business class seating based on the airlines and routes available. Major airlines operating here include Delta, American Airlines, and United.
• Westchester County Airport (HPN): Found in Westchester County, New York, just around 10 miles from Ossining, this airport caters to both domestic and international travelers. It connects to more than 110 domestic cities and around 10 international destinations. For added comfort, passengers can upgrade to premium economy or first class service, depending on the airline and route. Notable airlines servicing Westchester include JetBlue Airways, American Airlines, and Delta.

Top routes to Ossining

• Chicago (ORD/MDW) to Ossining (HPN/LGA), with one-way flights starting at around $70
• Orlando (MCO) to Ossining (HPN/LGA), with one-way airfare from around $45
• Miami (MIA) to Ossining (HPN/LGA), with one-way flights starting at around $50
• Atlanta (ATL) to Ossining (HPN/LGA), with one-way flights starting at around $35
• Tampa (TPA) to Ossining (HPN/LGA), with one-way fares starting at around $60

Cheapest routes to Ossining

• Atlanta (ATL) to Ossining (HPN/LGA), with cheap one-way fares from around $35
• Raleigh (RDU) to Ossining (HPN/LGA), with cheap one-way fares from around $40
• Charlotte (CLT) to Ossining (HPN/LGA), with low one-way fares from around $40
• Orlando (MCO) to Ossining (HPN/LGA), with low-cost one-way tickets from around $45
• Cleveland (CLE) to Ossining (HPN/LGA), with budget one-way fares from around $45

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

Top airlines with flights to Ossining

• Delta: Operating flights to both Westchester County Airport (HPN) and LaGuardia Airport (LGA), Delta represents roughly 35% of arrivals in Ossining. Passengers can expect an average one-way fare of around $250, with options for premium service such as premium economy, business, and first class depending on the specific route.
• American Airlines: Also serving Westchester County Airport (HPN) and LaGuardia Airport (LGA), American Airlines accounts for approximately 35% of arrivals to Ossining. Average one-way fares hover around $250, offering business and first class as premium cabin choices on certain routes.
• United: With operations to LaGuardia Airport (LGA), United captures about 11% of the arrivals to Ossining. The average one-way fare is around $280, and premium cabins may include both business class and first class, depending on the route.
• Southwest Airlines: Flying into LaGuardia Airport (LGA), Southwest Airlines comprises about 9% of arrivals to Ossining. Travelers can expect average one-way fares of around $240 for their journeys.
• Frontier Airlines: Operating flights to LaGuardia Airport (LGA), Frontier Airlines contributes approximately 2% of arrivals in Ossining. The average one-way fare is roughly $170, making it a budget-friendly option for travelers.

Best time to fly to Ossining

The most popular months for travelers to fly to Ossining are January, March, and April, when peak temperatures in Ossining can reach up to 49.8°F in April. If you prefer quieter travel, consider September, the least busy time to visit with temperatures around 66.9°F and typically the lowest average one-way fare (around $177), roughly 5% cheaper than the yearly average. Looking for additional cheaper months to fly? October, July, and May offer average one-way fares of around $180, 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 Ossining

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

*For members. Select hotels.

Arriving in Ossining

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

• Public transportation: From LaGuardia Airport, Junction Blvd. Station (a metro station) is located about 1.9 miles away by car, while Woodside Station (a train station) is approximately 3 miles away by car. For those looking to travel by sea, Flushing Seaport (a seaport) is situated about 3.7 miles from the airport by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Ossining, with options including free hotel shuttles and private rides, which can be arranged in advance.
• Car rental: Renting a car in Ossining is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Ossining 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 Ossining

• Congers: Congers is located 18 miles drive away from Ossining and is an ideal destination for families and outdoor enthusiasts. This vibrant city offers a variety of activities, including shopping and golfing. Visitors can explore notable attractions like Croton Point Park, perfect for family outings and outdoor adventures, or visit the historic Van Cortlandt Manor for a glimpse into the past. Don't miss the Rockland County Courthouse, a modern civic building, adding to the city's unique charm.
• Yonkers: Located 17 miles drive away from Ossining, Yonkers is a bustling city known for its family-friendly atmosphere and cultural experiences. Shoppers will enjoy the extensive shopping areas and centers available. Key highlights include the renowned Lincoln Center, a hub for the arts, and the tranquil Untermyer Gardens Conservancy, a perfect spot for a peaceful stroll. Central Park provides an urban oasis for families and outdoor lovers alike, making Yonkers a well-rounded destination.
• Sleepy Hollow: Sleepy Hollow is located 5 miles drive away from Ossining and is famous for its picturesque setting and enchanting atmosphere. Ideal for outdoor enthusiasts and families, this charming village features activities like shopping and theater. Explore the historic Lyndhurst Mansion, a stunning example of Gothic architecture, or enjoy the natural beauty at Croton Point Park. The Westchester County Center also offers cultural experiences, making Sleepy Hollow a delightful stop for travelers seeking romance and adventure.

Tips for short-haul flights to Ossining

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 by using mini toiletries, wearing your bulkiest clothing, and coordinating outfits in advance. This strategy also allows you to bypass the 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 beforehand and consider bringing a book. Remember to charge your devices fully before you board.
• Arrive at the airport in plenty of time—for both short and domestic flights, it’s advisable to arrive at least 1.5 to 2 hours prior to 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 Ossining

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

• Select your seat in advance—for longer flights, choosing your seat ahead of time is essential 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 may allow seat selection even earlier than this.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before departure for international flights to accommodate check-in, security, and immigration processes.
• 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 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 syncing your internal clock by changing your watch and sleep schedule to align with your destination's time zone. Aim 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 Ossining

The cheapest day to fly

Get started finding a cheap flight to Ossining 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 Ossining. 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 Ossining. 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 Ossining, 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 Ossining

The lowest price for round-trip flights to Ossining in 2026 starts from $210, while one-way tickets start from from $105. 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 Ossining. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Ossining

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

The most affordable airports to fly into

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

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 Ossining.

Stopover savings

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