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$59 Cheap Flights to Old Greenwich, CT

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Popular airlines to Old Greenwich

How much is the cheapest flight to Old Greenwich?

Prices were available within the past 7 days and start at $59 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Southwest Airlines
American Airlines
JetBlue Airways
Delta

Find the cheapest month to fly from Columbus (CMH) to White Plains (HPN)

From $200 - $350 per traveler.

What you need to know for your flight to Old Greenwich

Flights to Old Greenwich at a glance

Traveling to Old Greenwich is a breeze; simply select from a range of full-service or budget airlines, compare travel times, and choose the flight that best fits your budget and itinerary as you plan to discover the city’s renowned attractions and neighborhoods.

  • Major airports near Old Greenwich: John F. Kennedy International Airport (JFK), LaGuardia Airport (LGA), Westchester County Airport (HPN)
  • Closest airport to Old Greenwich: Westchester County Airport, HPN (around 8 miles)
  • Flights per week: 14,000+ flights arriving across Old Greenwich airports
  • Number of airlines that fly to Old Greenwich: around 90+ carriers

Popular airports near Old Greenwich

Old Greenwich is a charming city ideal for family getaways, urban exploration, and outdoor adventures. Visitors are drawn to its vibrant culture, entertainment options, and scenic landscapes. The area is conveniently served by three major airports, making travel hassle-free.

  • John F. Kennedy International Airport (JFK): Situated in Queens County, New York, approximately 29 miles from Old Greenwich, JFK caters to both domestic and international flights. It provides connections to over 195 domestic cities and more than 410 international locations. Travelers have the option to upgrade their experience with first class, premium economy, or business class seating for enhanced comfort, depending on the airline and route. Major airlines operating here include Delta, JetBlue Airways, and American Airlines.
  • LaGuardia Airport (LGA): Found in Queens County, New York, around 24 miles from Old Greenwich, LaGuardia offers both domestic and international services. It connects travelers to around 235 domestic cities and over 105 international destinations. Passengers can opt for upgrades to first class, premium economy, or business class seating for additional comfort, based on their selected routes and airlines. Notable carriers at this airport include Delta, American Airlines, and United.
  • Westchester County Airport (HPN): Located in Westchester County, New York, just about 8 miles from Old Greenwich, this airport provides both domestic and international flight options. It serves around 110 domestic cities and 10 international destinations. Travelers can enhance their journey by upgrading to premium economy or first class seating for a more comfortable experience, depending on the airlines and routes. Key airlines operating from here include JetBlue Airways, American Airlines, and Delta.

Top routes to Old Greenwich

  • Miami (MIA) to Old Greenwich (JFK/HPN/LGA), with one-way flights starting at around $50
  • Orlando (MCO) to Old Greenwich (JFK/HPN/LGA), with one-way tickets available from around $45
  • Los Angeles (LAX) to Old Greenwich (JFK/HPN/LGA), with one-way fares starting at around $100
  • Chicago (ORD/MDW) to Old Greenwich (JFK/HPN/LGA), with one-way fares starting at around $40
  • Atlanta (ATL) to Old Greenwich (JFK/HPN/LGA), with one-way tickets available from around $35

Cheapest routes to Old Greenwich

  • Manchester (MHT/MAN) to Old Greenwich (JFK), with low-cost one-way tickets from around $30
  • Providence (PVD) to Old Greenwich (JFK), with cheap one-way fares from around $35
  • Atlanta (ATL) to Old Greenwich (JFK/HPN/LGA), with low-cost one-way tickets from around $35
  • Chicago (ORD/MDW) to Old Greenwich (JFK/HPN/LGA), with cheap one-way fares from around $40
  • Raleigh (RDU) to Old Greenwich (JFK/HPN/LGA), with budget one-way fares from around $40

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

Top airlines with flights to Old Greenwich

  • Delta: Operating flights to John F. Kennedy International Airport (JFK), Westchester County Airport (HPN), and LaGuardia Airport (LGA), Delta represents about 31% of arrivals in Old Greenwich. The average fare for a one-way ticket is around $320. Depending on the route, premium service options may include premium economy, business class, and first class.
  • American Airlines: Serving John F. Kennedy International Airport (JFK), Westchester County Airport (HPN), and LaGuardia Airport (LGA), American Airlines accounts for approximately 26% of arrivals to Old Greenwich. The typical one-way fare is about $310. Premium service may feature premium economy, business class, and first class based on the route.
  • JetBlue Airways: With flights to John F. Kennedy International Airport (JFK), Westchester County Airport (HPN), and LaGuardia Airport (LGA), JetBlue holds around 14% of arrivals in Old Greenwich. The average cost for a one-way ticket is roughly $300. Premium options may include premium economy and business class depending on the route.
  • United: Providing service to John F. Kennedy International Airport (JFK) and LaGuardia Airport (LGA), United comprises about 5% of arrivals in Old Greenwich. The average one-way fare is approximately $490. Depending on the route, premium service options may include premium economy, business class, and first class.
  • Frontier Airlines: Flying into John F. Kennedy International Airport (JFK) and LaGuardia Airport (LGA), Frontier Airlines accounts for roughly 3% of arrivals to Old Greenwich. The average fare for a one-way ticket is around $170, making it an affordable travel choice for passengers.

Best time to fly to Old Greenwich

The most popular months for travelers to fly to Old Greenwich are January, March, and April, when peak temperatures in Old Greenwich can reach up to 49.8°F in April. If you prefer quieter travel, consider October, the least busy time to visit with temperatures around 57.9°F and typically the lowest average one-way fare (around $231), roughly 9% cheaper than the yearly average. Looking for additional cheaper months to fly? November, December, and May offer average one-way fares of around $238, making them good options for flexible travelers.

calendar iconMonthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinesscrowd level iconDemandprice iconAverage one-way Fare
January32.0°F (0.0°C)Light RainMostly SunnyModerately High$293
February33.3°F (0.7°C)Light RainMostly SunnyAverage$249
March39.7°F (4.3°C)Light RainMostly SunnyModerately High$258
April49.8°F (9.9°C)Light RainMostly SunnyModerately High$277
May59.7°F (15.4°C)Light RainMostly SunnyAverage$242
June68.7°F (20.4°C)Light RainMostly SunnyAverage$253
July75.7°F (24.3°C)Light RainMostly SunnyAverage$255
August74.7°F (23.7°C)Light RainMostly SunnyAverage$284
September68.2°F (20.1°C)Light RainMostly SunnyModerately Low$249
October57.9°F (14.4°C)Light RainMostly SunnyModerately Low$231
November46.4°F (8.0°C)Light RainMostly SunnyModerately Low$234
December38.5°F (3.6°C)Light RainMostly SunnyAverage$237

*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 Old Greenwich

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

*For members. Select hotels.

Arriving in Old Greenwich

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

  • Public transportation: From John F. Kennedy International Airport, Terminal 5, a metro station, is located just 0.2 miles away by walking, while Jamaica Locust Manor Station, a train station, is situated about 4.1 miles from the airport and is typically reached by car.
  • Hotel transfer: Transfers offer a convenient way to reach your hotel in Old Greenwich, with private rides that can be arranged in advance.
  • Car rental: Renting a car in Old Greenwich is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Old Greenwich 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 Old Greenwich

  • Stamford: Located 2 miles drive away from Old Greenwich, Stamford is a vibrant city that offers a mix of family-friendly activities and urban experiences. Visitors can enjoy shopping, catch a show at the local theater, or explore educational venues. Notable attractions include Greenwich Avenue, perfect for city exploration; the Historic South Norwalk, rich in culture; and the Stamford Museum and Nature Center, which promotes eco-friendly experiences in a picturesque setting.
  • Greenwich: Just 3 miles drive away from Old Greenwich, Greenwich is a charming city known for its family-oriented activities and outdoor adventures. Travelers can indulge in shopping and enjoy local theater performances. Key highlights include Greenwich Avenue, ideal for a city getaway; the Westchester County Center, a hub for the arts; and Manhattanville College, a modern university that adds to the vibrant atmosphere of the area.
  • Rowayton: Rowayton is located 9 miles drive away from Old Greenwich and is an enchanting neighborhood perfect for those seeking outdoor beauty and romantic scenery. This coastal gem offers opportunities for skiing in the winter and enjoying beach activities in the warmer months. Don’t miss local attractions like the Historic South Norwalk for cultural insights, The Glass House museum for architectural appreciation, and Greenwich Avenue for a taste of urban life.

Tips for short-haul flights to Old Greenwich

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, it’s often more economical to travel with just a carry-on. Optimize your packing by using mini toiletries, wearing your heaviest clothing, and carefully planning your outfits. This approach also allows you to 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 ahead of time, and bring along a book. Remember to fully charge your devices 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, taking into account possible 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 Old Greenwich

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

  • Select your seat in advance—especially for long flights, choosing your seat 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.
  • Arrive at the airport in plenty of time—aim to arrive at least 3 hours before departure for international flights to accommodate check-in, security, and immigration processes.
  • 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. Most airports offer free Wi-Fi for your convenience.
  • Adjust to the new time zone mid-flight—begin synchronizing your body clock by changing your watch and sleep schedule to align 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.

Frequently asked questions

What month is the cheapest to fly to Old Greenwich?
October is the cheapest month to travel to Old Greenwich. Demand is lower then, so fares are usually more affordable. Booking your trip outside of school breaks and major holidays can also help you save.
Which US cities have the cheapest flights to Old Greenwich?
Get cheap flights to Old Greenwich from Los Angeles, San Francisco and Boston. These cities usually offer the lowest fares to this popular destination. But keep in mind that holiday periods, demand and stopovers will also influence rates, so stay flexible and book when you spot a bargain.
Which US cities fly direct to Old Greenwich?
Pick from 58 US destinations that have direct flights to Old Greenwich. When you book on Expedia, check "Direct flights only" to find nonstop routes. Fly to Old Greenwich from any of these cities:
  • Los Angeles
  • San Francisco
  • Boston
  • Miami
  • Orlando
How to find a cheap flight to Old Greenwich?
Book in advance for the best chance of scoring cheap flights to Old Greenwich. Also, consider traveling during off-peak months like January and February. If you fly on a Thursday, you can save 16% on average compared to those departing on a Sunday.* Save time searching every day and track your flight prices using the Expedia app. We'll update you when fares change.*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 Old Greenwich?
While booking in advance is generally the best way to save cash, don't panic if your Old Greenwich vacation is last minute. It's still possible to find cheap flights to Old Greenwich, especially if your plans have some flexibility. Try changing your travel dates, exploring different ticket options or jetting out of another hub.
How far in advance should I book a flight to Old Greenwich?
For some of the best deals on domestic journeys, book your flight to Old Greenwich 28 days ahead of your travel dates. For international flights, it's two to four months in advance. This increases your chances of getting your preferred departure dates 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 Old Greenwich?
You'll save an average of 8% if you purchase tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to scoring a cheap flight to Old Greenwich, the key is good 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 Old Greenwich?
A total of 72 airlines connect 168 airports around the world to Old Greenwich. Here are some of the key airlines to Old Greenwich, where John F. Kennedy Intl. Airport (JFK) is the major entry point:
  • Delta Air Lines
  • JetBlue Airways
  • American Airlines
  • British Airways
Where do you fly into Old Greenwich?
Old Greenwich's main gateway is Westchester County Airport (HPN). If you'd like more nearby choices when flying to Old Greenwich, consider LaGuardia Airport (LGA), John F. Kennedy Intl. Airport (JFK) or MacArthur Airport (ISP). You can also fly to Old Greenwich through Tweed - New Haven Regional Airport (HVN).
How far is the airport from central Old Greenwich?
Arriving at Westchester County Airport (HPN) puts you roughly 8 mi northwest of central Old Greenwich.
Can I save money by booking an Old Greenwich trip package?
Book an Old Greenwich flight and hotel package deal on Expedia, and you could enjoy significant savings. It's simple to bundle your hotel and flight, and you can even add car rentals and activities to create your own personalized Old Greenwich getaway. Plus, there's nothing like the convenience of booking everything in the same place.
Can I change or cancel my flight to Old Greenwich?
It's often possible to change or cancel your flight to Old Greenwich. Many airlines let you cancel your flights for free within 24 hours of making your booking. However, some flights are non-refundable, and airlines may offer you credit for a future trip rather than a direct refund. To find affordable flights to Old Greenwich with flexible change policies, select the "No cancel fee" or "Changes included" filters when you search. Want more details? Visit our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

Book with confidence

Tips to find the cheapest flights to Old Greenwich

The cheapest day to fly

Get started finding a cheap flight to Old Greenwich 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 Old Greenwich. 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 Old Greenwich. 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 Old Greenwich, 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 Old Greenwich

The lowest price for round-trip flights to Old Greenwich in 2026 starts from from $118, while one-way tickets start from from $59. 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 Old Greenwich. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Old Greenwich

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

The most affordable airports to fly into

To view the cheapest airports to fly into for Old Greenwich, 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 Old Greenwich. 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 Old Greenwich 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 Old Greenwich

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 Old Greenwich.

Stopover savings

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

Tips to find the cheapest flights to Old Greenwich

Travel information

Destination airport
Westchester County
Destination airport IATA code
HPN
Destination city name
White Plains
Roundtrip price
$81

Trending flights to Old Greenwich

Prices were available within the past 7 days and start at $59 for one-way flights and $118 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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