Cheap Flights to Winchester: Winchester Flight Deals

View €82 flight on Tue, 13 Jan 2026Opens in a new window

Popular airlines to Winchester

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Cheap round-trip flights to Winchester

Prices were available within the past 7 days and start at €82 for one-way flights and €166 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, 6 Nov - Mon, 10 Nov
BWI
Baltimore
BOS
Boston
€166 Return, found 7 hours ago
€166
Return
found 7 hours ago
Select Delta flight, departing Thu, 6 Nov from Baltimore to Boston, returning Mon, 10 Nov, priced at €166 found 7 hours ago
American Airlines
Thu, 6 Nov - Mon, 10 Nov
BWI
Baltimore
BOS
Boston
€229 Return, found 7 hours ago
€229
Return
found 7 hours ago
Select American Airlines flight, departing Thu, 6 Nov from Baltimore to Boston, returning Mon, 10 Nov, priced at €229 found 7 hours ago
Aer Lingus
Fri, 30 Jan - Tue, 3 Feb
DUB
Dublin
BOS
Boston
€343 Return, found 2 days ago
€343
Return
found 2 days ago
Select Aer Lingus flight, departing Fri, 30 Jan from Dublin to Boston, returning Tue, 3 Feb, priced at €343 found 2 days ago
TAP Portugal
Fri, 6 Feb - Sun, 8 Feb
DUB
Dublin
BOS
Boston
€344 Return, found 1 day ago
€344
Return
found 1 day ago
Select TAP Portugal flight, departing Fri, 6 Feb from Dublin to Boston, returning Sun, 8 Feb, priced at €344 found 1 day ago
Icelandair
Wed, 21 Jan - Tue, 27 Jan
DUB
Dublin
BOS
Boston
€358 Return, just found
€358
Return
just found
Select Icelandair flight, departing Wed, 21 Jan from Dublin to Boston, returning Tue, 27 Jan, priced at €358 just found

Frequently asked questions

What is the name of Winchester's airport?
Most visitors like to fly into Logan Intl. Airport (BOS) when visiting Winchester.
What airport is best to fly into Winchester?
With just one major airport operating in Winchester, it won't take you too long to discover the best flight. You'll be taking off to Bradley International Airport, which is located around 97 kilometres from downtown.
How many airlines fly to Winchester?
Winchester is serviced by 45 airlines from at least 127 airports across the globe.
Which airlines fly to Winchester?
Typically, travellers choose to fly with American Airlines, JetBlue and Delta when going to Winchester. The majority of these flights come from Washington, with American Airlines flying this route the most frequently.
How many nonstop flights are there to Winchester?
With roughly 3,559 nonstop flights every week, you'll be touching down in Winchester before you can say, "Are we there yet?"
Where are the most popular flights to Winchester departing from?
A large number of flights to Winchester depart from Washington, New York and Chicago airports.
How long is the flight to Winchester Airport?
If you're flying to Winchester from Washington, you're looking at a flight duration of 1 hour and 31 minutes. Those setting off from New York can expect to be airborne for 1 hour and 19 minutes. From Chicago it's approximately 2 hours and 13 minutes away.
How to book the cheapest flight to Winchester?
If you want to save some cash on your trip to Winchester, then listen up! As any seasoned traveller knows, don't book at the very last minute. Fares are often highest just prior to the departure date. Another excellent way to nab the most competitive fare is to shop around. If your destination has a few airports, don't forget to look into the cost of flying into a smaller terminal. And finally, remember that the early bird catches the worm. Familiarise yourself with airfare costs and have your credit card ready to book your ticket as soon as you see a great bargain. The sweetest deals never last long.
Do you have any tips for my flight to Winchester?
We've pulled together all the info you need to make your flight a pleasant experience. Follow our tips and tricks and you'll be hightailing it through airport security and enjoying Winchester in no time at all. What to pack in your hand luggage:

  • It's simple — first, put in your passport, official ID, credit cards and daily medications. Next, you'll want some in-flight entertainment to while away the time. A juicy book and a laptop filled with your favourite movies are some wonderful options. If you intend to catch a few z's, a neck pillow and some noise-cancelling headphones will also be useful. Finally, find room for a few toiletry items so you'll step off the plane feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Double-check that you don't have a sharp object hiding in one of the compartments of your hand luggage. Other banned items include explosive or flammable goods, such as fuel and matches, and liquids and gels in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by wearing layers, and pick closed-toe, flat shoes like slip-ons.
  • Deep vein thrombosis (DVT) is a risk on long-haul flights. It's the result of blood clotting due to poor circulation and inactivity, so do some gentle leg and foot exercises in your seat and consider wearing compression tights or socks.

How to get through airport security fast when flying to Winchester?
As savvy travellers know, the secret is to be well prepared before you reach the security gate. That way, you'll be stepping onto that plane to Winchester in no time flat. Follow these tips and get your holiday off to a spectacular start:

  • Your travel documents and ID will need to be presented to security personnel. Have them close by so you don't hold up the queue.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other contents of your pockets, like your headphones, will be required to go through the X-ray machine. Make the whole process faster by removing them before your turn arrives.
  • All your electronic devices, including your phone and laptop, are also required to be separately scanned.
  • Want to bring along your favourite perfume? Not a problem. As long as the volume is no greater than 3.4 ounces (100 millilitres) and it's stored in a zip-lock bag, you're permitted to bring it with you in your carry-on luggage.
  • Lightweight sneakers are a good footwear choice as you're less likely to be asked to remove them when passing through security. Hiking boots and heavier-style shoes are often subjected to additional screening.
  • Airlines will not allow any sharp or pointed objects in your carry-on baggage. If you must bring these kinds of items, put them in your checked baggage.

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
€85

Trending flights to Winchester

Prices were available within the past 7 days and start at €82 for one-way flights and €166 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Aer Lingus
Fri, 30 Jan - Tue, 3 Feb
DUB
Dublin
BOS
Boston
€343 Return, found 2 days ago
€343
Return
found 2 days ago
Select Aer Lingus flight, departing Fri, 30 Jan from Dublin to Boston, returning Tue, 3 Feb, priced at €343 found 2 days ago

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