S$359 Cheap Flights to Winchester

View S$359 flight on Sat, 21 Jun, 2025Opens in a new window

Popular airlines to Winchester

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Cheap round-trip 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
Thu, 26 Jun - Thu, 3 Jul
MEX
Mexico City
PVD
Providence
S$1,012 Return, found 22 hours ago
S$1,012
Return
found 22 hours ago
Select American Airlines flight, departing Thu, 26 Jun from Mexico City to Providence, returning Thu, 3 Jul, priced at S$1,012 found 22 hours ago
United
Thu, 26 Jun - Thu, 3 Jul
MEX
Mexico City
PVD
Providence
S$1,012 Return, found 22 hours ago
S$1,012
Return
found 22 hours ago
Select United flight, departing Thu, 26 Jun from Mexico City to Providence, returning Thu, 3 Jul, priced at S$1,012 found 22 hours ago
Delta
Thu, 26 Jun - Thu, 3 Jul
MEX
Mexico City
PVD
Providence
S$1,169 Return, found 22 hours ago
S$1,169
Return
found 22 hours ago
Select Delta flight, departing Thu, 26 Jun from Mexico City to Providence, returning Thu, 3 Jul, priced at S$1,169 found 22 hours ago
Air Canada
Tue, 22 Jul - Tue, 29 Jul
MEX
Mexico City
LEB
Lebanon
S$1,268 Return, found 5 days ago
S$1,268
Return
found 5 days ago
Select Air Canada flight, departing Tue, 22 Jul from Mexico City to Lebanon, returning Tue, 29 Jul, priced at S$1,268 found 5 days ago
Cathay Pacific
Sun, 22 Jun - Sun, 13 Jul
SIN
Singapore
BOS
Boston
S$1,330 Return, found 13 hours ago
S$1,330
Return
found 13 hours ago
Select Cathay Pacific flight, departing Sun, 22 Jun from Singapore to Boston, returning Sun, 13 Jul, priced at S$1,330 found 13 hours ago

Find Your Flights to Winchester EEN

Cheap flights to Winchester (EEN)

Get started finding a cheap flight to Winchester on Expedia by either choosing a deal on this page or using the search bar to enter your travel dates, origin airport and whether you want a return or one-way airfare. You can filter for flexibility, number of stops, airline and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Winchester.

Return prices range from S$1,012 - S$1,330 and one-ways Winchester start as low as S$359.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

 

Airlines that fly to Winchester (EEN)

You have several options for which airline you choose to travel with to Winchester. There are 10 airlines flying into EEN: Air Canada, Delta, Aeromexico, United, American Airlines, Cathay Pacific. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check in a bag or bring hand baggage, it's worth checking whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked in/hand baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programmes may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel on one online platform.

 

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at optimal times. Airfare to Winchester (EEN) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to EEN in June and in June for one-ways.

 

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24 hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

What is the name of Winchester's airport?
Winchester is served by a single airport, Logan Intl. Airport (BOS).
How many airlines fly to Winchester?
There are 39 airlines that jet into Winchester from 119 airports around the world.
Which airlines fly to Winchester?
Most often, travellers opt to fly with JetBlue Airways, American Airlines and Delta Air Lines when going to Winchester. The largest number of these flights come from Washington, with JetBlue Airways flying this route the most frequently.
How many nonstop flights are there to Winchester?
Flying to somewhere new is much simpler when there aren't any annoying stopovers to slow you down. If you're jetting off to Winchester, the great news is that there are around 3,836 direct flights operating every week.
Where are the most popular flights to Winchester departing from?
Flights to Winchester from Chicago, Atlanta and New York airports are very popular.
How long is the flight to Winchester Airport?
Which airport you depart from determines how much of the in-flight entertainment you'll get to enjoy. From Washington to Winchester, the average flight time is 1 hour and 27 minutes. From Queens Village it's more or less 1 hour and 13 minutes, and from Chicago it's 2 hours and 9 minutes.
How to book the cheapest flight to Winchester?
Don't leave locking in your flight to Winchester until the very last minute. That's one move seasoned jet-setters use to get the best deals. Booking well in advance means more choices and less expensive flights. Don't stop there, though. Do some research and see if there are multiple airports at your destination. Prices often differ depending on which airport you pick. Make sure you compare prices across air carriers too. Last of all, another simple way to save a few dollars is be ready to book fast. If you stumble on a terrific deal, don't hold off --- grab it while you've got the chance.
How to survive the flight to Winchester?
Wherever you're jetting in from, flying can be a pleasant experience if you've planned ahead. Follow these top travel tips that will help get your Winchester holiday started on the right note.What to pack in your hand luggage:
  • Travelling on a plane can be a great experience if you bring the right stuff. First of all you'll need toiletry items, such as deodorant, toothpaste and a toothbrush, a clean pair of socks and a magazine or two. Next, find room in your bag for your laptop, a charger, your medications and maybe a cosy neck pillow as well. Last, but definitely not least, remember to take your passport, travel docs and your credit cards.

Do not pack the following items in your hand luggage:
  • While the list of prohibited items can differ between airlines, the general rule of thumb is nothing sharp, flammable or explosive. This includes screwdrivers, knives, fireworks and fuel. Sporting equipment like ski poles, and items that could injure passengers, such as pepper spray and guns, aren't allowed in the cabin either.

What to wear on a flight:
  • Comfort should be your highest priority when choosing what to wear on your flight. Consider your footwear choice with care too, as swollen feet are quite common. Shoes which are flat and slightly roomy are always a sensible way to go.
  • The condition known as DVT (deep vein thrombosis) is a potential risk on long-haul flights. It's the result of blood clotting due to poor circulation. Walking up and down the aisle and doing foot and leg exercises while seated is a great way to prevent this from occurring. Wearing a quality pair of compression tights or socks is also recommended.

How to get through airport security fast when flying to Winchester?
A little pre-planning before you arrive at the airport will make your getaway to Winchester a breeze. Here are some useful tips for a stress-free journey past security:
  • Airport security personnel first need to see that you have a valid passport and travel documents before you can proceed any further. Keep them close by.
  • After that, both you and your carry-on luggage must be X-rayed. To speed things up, take off anything that is likely to set the alarm off. Items like your coat, belt and earphones will be required to go through the machine.
  • All your electronic devices, including your tablet and phone, will also need to be scanned.
  • Travelling with a new hand and nail cream? Not a problem. As long as the volume is no greater than 3.4 ounces (100 milliliters) and it's stored in a zip-lock bag, you're allowed to bring it with you in your carry-on.
  • There's a chance you'll be asked to take your shoes off for scanning, so wearing slip-on shoes is always a wise idea.
  • Airlines won't allow any pocket knives or other sharp items in your carry-on baggage. If you need to bring these kinds of items, pack them safely in your checked luggage.

Flights to Winchester information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Destination city name
Boston
Return price
S$200

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.

United
Sat, 21 Jun - Sat, 12 Jul
SIN
Singapore
BOS
Boston
S$1,226 Return, found 1 hour ago
S$1,226
Return
found 1 hour ago
Select United flight, departing Sat, 21 Jun from Singapore to Boston, returning Sat, 12 Jul, priced at S$1,226 found 1 hour ago
*Available to Expedia members.