A town with a prominent church, a large building with a clock tower, and a mix of residential and commercial buildings surrounded by greenery.

Cheap Flights to Winchester: Winchester Flight Deals

View €342 flight on Fri, 6 Nov 2026Opens in a new window

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Cheap round-trip flights to Winchester

Prices were available within the past 7 days and start at €342 for one-way flights and €335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
JetBlue Airways
Icelandair
British Airways
Iberia

Find the cheapest month to fly from Columbus (CMH) to Boston (BOS)

From €169 - €285 per traveller.

Frequently asked questions

What is the name of Winchester's airport?
Logan Intl. Airport (BOS) is the only airport serving Winchester.
How far is Logan Intl. Airport (BOS) from central Winchester?
If you plan on staying in central Winchester, it's a good idea to organise how you'll get into the city before you arrive. The downtown area is 14 kilometres from Logan Intl. Airport (BOS).
What airport is best to fly into Winchester?
Step through the glass doors of Logan Intl. Airport and your Winchester adventure will have begun! The city's main airport, it's located 14 kilometres from the downtown streets.
How many airlines fly to Winchester?
Winchester is serviced by 43 airlines from at least 121 airports around the world.
Which airlines fly to Winchester?
Winchester receives most of its flights from Delta, JetBlue and American Airlines with Delta being the favourite choice of airline. New York is the most popular city for travellers to set off from.
How many nonstop flights are there to Winchester?
With roughly 3,070 direct flights operating every week, you'll be touching down in Winchester before you have time to say, "Are we there yet?"
Where are the most popular flights to Winchester departing from?
A large number of flights to Winchester set off from New York, Washington and Chicago airports.
How long is the flight to Winchester Airport?
If it's New York you're departing, you'll be midair for around 1 hour and 19 minutes before you touchdown in Winchester. Terminal to terminal from Washington takes around 1 hour and 36 minutes and from Chicago, the flight time is 2 hours and 20 minutes.
How to book the cheapest flight to Winchester?
If you'd like to save some cash on your Winchester holiday, then listen up! As any experienced traveller knows, don't book at the very last minute. Fares are usually more expensive close to the departure date. Don't stop there, however. Do some research and see if there are a couple of airports at your destination. Ticket prices often differ depending on which airport you pick. Don't forget to compare prices across airlines too. Lastly, be ready to lock in your seat quickly if you stumble on a great deal. It might not stick around for too long! With a bit of knowledge and some good fortune, the ideal fare can be yours.
Do you have any tips for my flight to Winchester?
If you're poorly prepared, airports and flying can be overwhelming. But there's no need to panic. Follow these handy hints and enjoy a comfortable start to your time in Winchester. What to pack in your hand luggage:
  • It's simple — first, pack your passport, travel documents, wallet and medications. Next, you'll want some extra in-flight entertainment to help pass the time. A juicy novel and a tablet filled with your favourite shows are always good options. If you hope to catch forty winks, a comfy neck pillow and some earplugs will also be useful. Finally, make room for a toothbrush and some deodorant to ensure you arrive at your destination feeling fresh and ready to go.
Do not pack the following items in your hand luggage:
  • Check carefully that you don't have a pocket knife hiding in your hand luggage. Other prohibited items include explosive or flammable goods, such as aerosol cans and fuel, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 millilitres).
What to wear on a flight:
  • Comfort should be your main priority when deciding what to wear on your flight. Loose, breathable clothing is a sensible option, as are flat, slightly roomy shoes.
  • It's likely you've heard about deep vein thrombosis (DVT), a blood clotting condition caused by long periods of sitting. To minimize your risk on board, stay hydrated, consider wearing compression socks or tights and move your legs and feet often.
How to get through airport security fast when flying to Winchester?
The secret is to be organised before you arrive at the airport security gate. That way, you'll be hopping onto that plane to Winchester in no time flat. Follow these helpful tips and get your holiday off to a flying start:
  • First things first. Your passport and boarding pass will need to be presented to security personnel. Have them easily accessible so you don't hold up the queue.
  • Time to strip down. Well kind of. Your belt, coat, keys and other items in your pocket, like your headphones, will be required to go through the X-ray machine. Make your life easier by removing them as your turn draws near.
  • Your electronic devices like laptops and phones will also need to go on a tray to be scanned. No need to worry though, you'll be back online before you know it.
  • Remember to remove gels and liquids from your hand luggage. They often need to be sent through the X-ray machine separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a single quart-size (one litre), clear zip-lock bag.
  • The right choice of footwear can save you several minutes. Boots and heavy shoes are often required to be removed and separately scanned. Slip-on shoes are usually not.
  • Airlines will not allow any sharp objects in your carry-on luggage. If you must bring these kinds of items, pack them in your checked luggage.

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Winchester. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Winchester. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Winchester, or are just on the lookout for the best flights to Winchester, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Winchester to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Return price
€192

Trending flights to Winchester

Prices were available within the past 7 days and start at €342 for one-way flights and €335 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
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