Cheap Flights to Winchester

View NZ$688 flight on Sun, 15 Feb 2026Opens in a new window

Popular airlines to Winchester

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Cheap Tickets to Winchester

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sun, 15 Feb - Sun, 22 Feb
CYS
Cheyenne
RUT
Rutland
NZ$1,433 Return, found 1 day ago
NZ$1,433
Return
found 1 day ago
Select United flight, departing Sun, 15 Feb from Cheyenne to Rutland, returning Sun, 22 Feb, priced at NZ$1,433 found 1 day ago

Winchester Flights

The Winchester experience you’ve always wanted

Catching a flight to Winchester is easier than it’s ever been when you use Expedia to plan your escape. A great holiday starts with great selection, and we have an amazing amount of Winchester flight deals. A quick search on Expedia.co.nz will show you cheap tickets to Winchester in mere moments, from overnight flights to weekend getaways. Trying to earn frequent flyer points? We even make it easy for you to stay loyal to your preferred airline.

Been a while since you’ve travelled?

If you haven’t flown recently, you might like some insider information. In fact, even seasoned travellers should check out our blog. Featuring hundreds of articles written by our very own experts, our blog keeps you informed about all the fantastic attractions and things to do in the world’s most popular destinations, so you know just what to pack. Get ready for great advice on trip preparation and seeing the sights—then get ready to fly!

Bundle your room and flight to travel for less

Package your flights with your hotel booking in Winchester, and your trip will become even cheaper. By making all of your reservations with us, you’ll save money and time, plus have the peace of mind that comes with booking all of your arrangements in one place. It may seem like magic, but it’s just the Expedia.co.nz way.

A holiday at the tips of your fingers

Take the high-tech road when you use our Expedia app to plan your holiday to Winchester. Our handy app allows you to reserve flights and hotels at any time of day, on any type of phone, because it’s available on both Android and iOS. You’ll also benefit from exclusive deals, have a chance to earn extra points, and can keep your itinerary at your fingertips. No matter where you are, count on our app to help you get where you’re going.

Register for Frequent Flyer Rewards

If you enjoy being pampered every once in a while, register with our Expedia Rewards program to get exclusive offers and discounts you won’t find anywhere else. Expedia Rewards grants you member-only benefits, plus price guarantees on your room rates. We can even help you rack up frequent flyer points more quickly. Plus, by signing up, you can book our Unreal Deals, which, when bundled with your room, could save you the cost of a whole plane ticket.

Start planning and start packing

Expedia.co.nz makes it easy to find cheap flights to Winchester NZ$1,433. With such amazing deals, why wait any longer to book your trip? Start searching today, and we’ll see you soon in Winchester.

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.

Flights to Winchester information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Return price
NZ$545

Trending flights to Winchester

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Tue, 20 Jan - Sat, 31 Jan
AKL
Auckland
BOS
Boston
NZ$1,864 Return, found 2 days ago
NZ$1,864
Return
found 2 days ago
Select Air Canada flight, departing Tue, 20 Jan from Auckland to Boston, returning Sat, 31 Jan, priced at NZ$1,864 found 2 days ago
*Available to Expedia members.