Cheap Flights to Winchester

View AU$593 flight on Mon, 9 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.

Air Canada
Tue, 27 Jan - Tue, 3 Feb
SYD
Sydney
BOS
Boston
AU$1,261 Return, found 1 hour ago
AU$1,261
Return
found 1 hour ago
Select Air Canada flight, departing Tue, 27 Jan from Sydney to Boston, returning Tue, 3 Feb, priced at AU$1,261 found 1 hour ago
American Airlines
Mon, 11 May - Sun, 24 May
MEL
Melbourne
BOS
Boston
AU$1,291 Return, found 13 hours ago
AU$1,291
Return
found 13 hours ago
Select American Airlines flight, departing Mon, 11 May from Melbourne to Boston, returning Sun, 24 May, priced at AU$1,291 found 13 hours ago
Delta
Sun, 19 Apr - Sun, 26 Apr
MEL
Melbourne
BOS
Boston
AU$1,332 Return, found 6 days ago
AU$1,332
Return
found 6 days ago
Select Delta flight, departing Sun, 19 Apr from Melbourne to Boston, returning Sun, 26 Apr, priced at AU$1,332 found 6 days ago
United
Fri, 16 Jan - Sun, 1 Feb
MEL
Melbourne
BOS
Boston
AU$1,422 Return, just found
AU$1,422
Return
just found
Select United flight, departing Fri, 16 Jan from Melbourne to Boston, returning Sun, 1 Feb, priced at AU$1,422 just found
Qantas Airways
Tue, 8 Sept - Wed, 23 Sept
SYD
Sydney
BOS
Boston
AU$1,471 Return, found 11 hours ago
AU$1,471
Return
found 11 hours ago
Select Qantas Airways flight, departing Tue, 8 Sept from Sydney to Boston, returning Wed, 23 Sept, priced at AU$1,471 found 11 hours ago

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

September is typically the cheapest month to fly

From AU$154 - AU$443 per traveller.

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Winchester Flights

Have the time of your life in Winchester

Flying to Winchester is now easier than ever when you use Expedia to book your trip. We’ve got an extensive catalogue of Winchester flight deals, giving you the greatest number of options to choose from. Whether you prefer to fly on weekdays or weekends, in the morning or at night, a quick search on Expedia.com.au will help you find cheap tickets to Winchester in seconds. We even make it simple for you to stick with a certain airline if you’re trying to rack up frequent flyer points.

Tips for flying and packing light

If it’s been a while since you’ve travelled, you might be due for a refresher when it comes to flying. That’s where our helpful blog, Out There Starts Here, comes in. Wondering whether to pack for fine dining or more casual eats? Or whether you really need to bring a jacket? Written by seasoned travel experts, the articles on our blog provide you with the latest details about certain destinations, so you know just what to expect. Check out some of our recent articles for the smartest ways to see the sights.

Fly for less when you bundle airfare and accommodation

Our already low airfares are even more affordable when you bundle your flights with a stay at one of the hotels in Winchester. By booking all of your travel plans with us, you’ll save time and money, and enjoy the convenience of having all of your arrangements in one place.

Get the power of planning in the palm of your hand

Booking your trip to Winchester, Boston has never been easier than when you use our mobile app to plan your dream getaway. The Expedia App is available on both Android and iOS, allowing you to reserve flights and hotels at any time of day, no matter what kind of phone you use. You’ll also get exclusive offers, receive flight updates, and can earn extra points. Wherever you are, the Expedia App helps you get where you want to be.

Join the Expedia Rewards Program

If you enjoy the finer things in life, sign up for our rewards program to receive exclusive benefits when you book with us. Expedia Rewards opens the door to member-only deals, +VIP Access hotel benefits, and earning Expedia Rewards points, that you can redeem your way. You’ll also get access to Unreal Deals that could save you the price of a plane ticket to Winchester when bundled with your accommodation.

What are you waiting for?

Expedia.com.au helps you find cheap flights to Winchester AU$989. So why wait another second to begin planning your trip? Start your search right now, and you could be boarding the next Winchester-bound flight. Bon voyage!

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.

Flights to Winchester information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Return price
AU$988

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.

American Airlines
Sat, 7 Feb - Sat, 4 Apr
BNE
Brisbane
BOS
Boston
AU$989 Return, found 11 hours ago
AU$989
Return
found 11 hours ago
Select American Airlines flight, departing Sat, 7 Feb from Brisbane to Boston, returning Sat, 4 Apr, priced at AU$989 found 11 hours ago

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