Cheap Flights to Winchester: Winchester Flight Deals

View €257 flight on Wed, 10 Sep 2025Opens 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 €257 for one-way flights and €298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fly Play
Wed, 10 Sep - Sat, 13 Sep
DUB
Dublin
BOS
Boston
€298 Return, found 13 hours ago
€298
Return
found 13 hours ago
Select Fly Play flight, departing Wed, 10 Sep from Dublin to Boston, returning Sat, 13 Sep, priced at €298 found 13 hours ago
Icelandair
Sat, 29 Nov - Sat, 6 Dec
DUB
Dublin
BOS
Boston
€339 Return, found 4 days ago
€339
Return
found 4 days ago
Select Icelandair flight, departing Sat, 29 Nov from Dublin to Boston, returning Sat, 6 Dec, priced at €339 found 4 days ago
TAP Portugal
Wed, 26 Nov - Tue, 2 Dec
DUB
Dublin
BOS
Boston
€343 Return, found 2 days ago
€343
Return
found 2 days ago
Select TAP Portugal flight, departing Wed, 26 Nov from Dublin to Boston, returning Tue, 2 Dec, priced at €343 found 2 days ago
British Airways
Tue, 25 Nov - Tue, 2 Dec
DUB
Dublin
BOS
Boston
€360 Return, found 3 days ago
€360
Return
found 3 days ago
Select British Airways flight, departing Tue, 25 Nov from Dublin to Boston, returning Tue, 2 Dec, priced at €360 found 3 days ago
Aer Lingus
Sun, 23 Nov - Thu, 4 Dec
DUB
Dublin
BOS
Boston
€364 Return, found 4 days ago
€364
Return
found 4 days ago
Select Aer Lingus flight, departing Sun, 23 Nov from Dublin to Boston, returning Thu, 4 Dec, priced at €364 found 4 days ago

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

September is typically the cheapest month to fly

From €73 - €138 per traveller.

Graph displaying average flight prices per month

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.

Frequently asked questions

What is the name of Winchester's airport?
If you're travelling by air, you won't have to ponder too long which airport to choose. Winchester has just one -- Logan Intl. Airport (BOS).
How far is Logan Intl. Airport (BOS) from central Winchester?
If you're staying in central Winchester, it's wise to organise how you'll get into the city before you arrive. The downtown area is about 14 kilometres from Logan Intl. Airport (BOS).
What airport is best to fly into Winchester?
Travellers from across the globe pass through Logan Intl. Airport each day. Get off the plane, pick up your bags and you'll find yourself 14 kilometres from the central Winchester streets.
How many airlines fly to Winchester?
Winchester is serviced by 38 air carriers from 118 airports across the globe.
Which airlines fly to Winchester?
Most often, travellers fly with JetBlue Airways, American Airlines and Delta Air Lines when heading off to Winchester. The majority of these flights depart from Washington, with JetBlue Airways flying this route the most frequently.
How many nonstop flights are there to Winchester?
Flying to a new place is much easier when there aren't any stopovers involved. If you're jetting off to Winchester, the great news is that there are 3,384 direct flights operating every week.
Where are the most popular flights to Winchester departing from?
Travellers often jet off from New York, Chicago and Atlanta airports when heading to Winchester.
How long is the flight to Winchester Airport?
Which city you depart from determines how much of the in-flight entertainment you'll get to see. From Washington to Winchester, the average flight time is 1 hour and 33 minutes. From Queens Village it takes about 1 hour and 18 minutes, and from Chicago it's 2 hours and 16 minutes.
How to book the cheapest flight to Winchester?
We've all come across those travellers who manage to grab incredibly cheap airfares wherever they go. Want to know how to do it for your Winchester holiday? Don't leave it until the last moment to lock in your flight. Another excellent way to nab a bargain is to shop around. If your destination has a few airports, research the cost of flying into a less busy terminal. Finally, be prepared to book quickly if you find an irresistible price. It might not stick around for long! With a bit of knowledge and a little good fortune, the ideal airfare can be yours.
How to survive the flight to Winchester?
We've pulled together all the info you need to make your flight a pleasant experience. Follow our tips and you'll be cruising through the airport and seeing the best of Winchester before you know it.What to pack in your hand luggage:

  • Firstly, and most importantly, pack in your passport, travel documents, wallet and vital medications. Next, you'll want some entertainment to while away the time. A thrilling book and a laptop crammed with your favourite shows are always good options. If you intend to take a quick nap, a quality neck pillow and a pair of earplugs will also be useful. Finally, squeeze in a toothbrush and some deodorant so you'll arrive at your destination looking and feeling fresh.

Do not pack the following items in your hand luggage:

  • Double-check that you don't have sharp objects (like a knife or scissors) lurking in one of the zippers of your carry-on luggage. Other restricted items include explosive or flammable products, such as fuel and matches, and gels and liquids in containers with a volume of more than 3.4 ounces (100 milliliters).

What to wear on a flight:

  • Your number one priority is to be as comfortable as you can. Layer yourself up in natural-fibre clothing and pack a cardigan in case it gets cold in the cabin. Opt for flat, well-fitting shoes as your feet may swell during the journey. Leave the stilettos and heavy hiking boots in your checked baggage.
  • The serious condition by the name of DVT (deep vein thrombosis) is a potential risk on long-haul flights. It's the result of blood clotting due to inactivity and poor circulation. Walking around the cabin and doing regular leg and foot exercises in your seat is a great way to prevent this happening. Wearing a good-quality pair of compression socks or tights also helps reduce the risk.

How to get through airport security fast when flying to Winchester?
It's simple --- be prepared. We've compiled some top tips for a hassle-free trip through security. Look out Winchester, here you come:

  • Security personnel first need to verify that you have a valid ID and matching travel documents before you're allowed to proceed any further. Have them in your hand, ready for inspection.
  • The X-ray machine is up next. Empty your pockets and remove anything metal that is likely to set off the alarm. This includes things like headphones or earphones, as well as heavy coats or jackets. They'll all need to go on the X-ray conveyor belt.
  • All electronic devices, including your laptop and phone, will also need to be scanned separately.
  • Any gels or liquids, such as hair oil or hand cream, that you want to bring on board need to be in containers no greater than 3.4 ounces (100 milliliters). They must also all fit inside a quart-size (one litre), zip-lock bag.
  • It's also likely that you'll need to remove your shoes to be X-rayed, so wearing slip-on sneakers is always a good idea.
  • Sharp items are not allowed on board. They'll be confiscated at security, so pack them in your checked suitcase.

Flights to Winchester information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Return price
€259

Trending flights to Winchester

Prices were available within the past 7 days and start at €257 for one-way flights and €298 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fly Play
Wed, 10 Sep - Sat, 13 Sep
DUB
Dublin
BOS
Boston
€298 Return, found 13 hours ago
€298
Return
found 13 hours ago
Select Fly Play flight, departing Wed, 10 Sep from Dublin to Boston, returning Sat, 13 Sep, priced at €298 found 13 hours ago
*Available to Expedia members.