Cheap Flights to Winchester

View AU$754 flight on Thu, 25 Sep. 2025Opens in a new window

Popular airlines to Winchester

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 35% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

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.

American Airlines
Wed, 13 Aug. - Sat, 30 Aug.
SYD
Sydney
BOS
Boston
AU$1,254 Return, found 5 days ago
AU$1,254
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug. from Sydney to Boston, returning Sat, 30 Aug., priced at AU$1,254 found 5 days ago
United
Thu, 11 Sep. - Mon, 13 Oct.
MEL
Melbourne
BOS
Boston
AU$1,271 Return, found 3 days ago
AU$1,271
Return
found 3 days ago
Select United flight, departing Thu, 11 Sep. from Melbourne to Boston, returning Mon, 13 Oct., priced at AU$1,271 found 3 days ago
Air Canada
Sun, 21 Sep. - Tue, 21 Oct.
SYD
Sydney
BOS
Boston
AU$1,274 Return, found 1 day ago
AU$1,274
Return
found 1 day ago
Select Air Canada flight, departing Sun, 21 Sep. from Sydney to Boston, returning Tue, 21 Oct., priced at AU$1,274 found 1 day ago
Jetstar
Mon, 18 Aug. - Thu, 20 Nov.
AVV
Melbourne
BOS
Boston
AU$1,280 Return, found 11 hours ago
AU$1,280
Return
found 11 hours ago
Select Jetstar flight, departing Mon, 18 Aug. from Melbourne to Boston, returning Thu, 20 Nov., priced at AU$1,280 found 11 hours ago
Delta
Wed, 8 Oct. - Sun, 26 Oct.
SYD
Sydney
BOS
Boston
AU$1,281 Return, found 4 days ago
AU$1,281
Return
found 4 days ago
Select Delta flight, departing Wed, 8 Oct. from Sydney to Boston, returning Sun, 26 Oct., priced at AU$1,281 found 4 days ago

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

November is typically the cheapest month to fly

From AU$135 - AU$518 per traveller.

Graph displaying average flight prices per month

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$1,254. 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?
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
AU$1,254

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
Wed, 13 Aug. - Sat, 30 Aug.
SYD
Sydney
BOS
Boston
AU$1,254 Return, found 5 days ago
AU$1,254
Return
found 5 days ago
Select American Airlines flight, departing Wed, 13 Aug. from Sydney to Boston, returning Sat, 30 Aug., priced at AU$1,254 found 5 days ago
*Available to Expedia members.