S$93 Cheap Flights 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 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards

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.

Delta
American Airlines
Delta
Japan Airlines
Air Canada
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Find Your Flights to Winchester CHA

Cheap flights to Winchester (CHA)

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$186 - S$1,458 and one-ways Winchester start as low as S$93.

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 (CHA)

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

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 (CHA) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to CHA in February and in February 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 has several airports, but most visitors touch down at Hartsfield-Jackson Atlanta Intl. Airport (ATL).
How many airlines fly to Winchester?
Winchester is serviced by 27 air carriers from 215 airports around the world.
Which airlines fly to Winchester?
Winchester receives the largest number of flights from Delta Air Lines, United Airlines and American Airlines with Delta Air Lines being the number one choice of carrier. Chicago is the most popular city for travellers to depart from.
How many nonstop flights are there to Winchester?
Planning an awesome Winchester getaway is a walk in the park when there are 8,781 direct flights each week to choose from.
Where are the most popular flights to Winchester departing from?
The most popular flights to Winchester set off from Dallas, Chicago and Houston airports.
How long is the flight to Winchester Airport?
If you’re heading to Winchester from Chicago, you’ll have a flight time of 1 hour and 45 minutes. Those departing from Washington should expect to be airborne for around 2 hours and 2 minutes. From Dallas it’s 1 hour and 54 minutes away.
How to book the cheapest flight to Winchester?
Don’t leave locking in your flight to Winchester until the last minute. That’s one trick well-versed jet-setters use to get the best deals. Booking ahead means more options and more affordable flights. Don’t stop there, however. Do some research and see if there are multiple airports at your destination. Ticket prices often differ depending on the airport you pick. Remember to compare fares across airlines as well. Last but not least, another easy way to save some money is be ready to book fast. If you see an irresistible bargain, don’t think twice — snap it up while you’ve got the chance.
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 insider tips and you’ll be cruising through airport security and exploring Winchester in no time flat.What to pack in your hand luggage:

  • Flying can be a great experience if you’ve got all the right gear. Firstly, you’ll want a few basic toiletry items, such as a toothbrush and hairbrush, a spare pair of socks and a few magazines. Secondly, find a spot in your carry-on bag for your electronic gadgets, chargers, any vital medications and perhaps a proper neck pillow as well. Last, but definitely not least, don’t forget to bring your passport, travel documents and your bank cards.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between airlines, the general rule to follow is nothing flammable, sharp or explosive. This includes things like screwdrivers, knives, spray paint and flares. Sports equipment like bows and arrows, and items that could harm passengers, such as swords and guns, can’t come on board with you either.

What to wear on a flight:

  • Comfort really should be your number one priority when picking what to wear on your flight. Consider your footwear carefully too, as swollen feet can be a side effect of flying. Slightly roomy, flat shoes are always a sensible way to go.
  • A condition known as DVT (deep vein thrombosis) is a risk on long-haul flights. It’s the result of blood clotting due to poor circulation. Walking around the cabin and doing regular foot and leg exercises in your seat is a great way to prevent this happening. Wearing a good pair of compression socks or tights may also help.

How to get through airport security fast when flying to Winchester?
It’s simple — be prepared. We’ve pulled together some useful tips for a hassle-free trip through airport security. Look out Winchester, here you come:

  • Airport security personnel first need to verify that you have a valid passport and matching travel documents before anything else. Have them close by, ready for inspection.
  • After that, both you and your hand luggage will be X-rayed. To speed things up, take off anything that is likely to set the alarm off. Personal belongings such as your belt, coat and headphones will be required to go through the machine.
  • Your electronic devices like laptops and phones will also need to go on a tray for inspection. No need to worry though, you’ll be back online soon enough.
  • Don’t forget to remove liquids and gels from your hand luggage. They usually need to be sent through the X-ray machine separately. Each product should be in a container no larger than 3.4 ounces (100 milliliters) and everything must fit inside a quart-size (one litre), clear zip-close bag.
  • The right choice of footwear can save you several valuable minutes. Hiking boots are often required to be removed and X-rayed separately. Lightweight sneakers are usually not.
  • Airlines won’t allow any sharp or pointed objects in the cabin. If you need to bring these kinds of items, put them in your checked luggage.

Flights to Winchester information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Destination city name
Nashville
Return price
S$185

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.

Japan Airlines
*Available to Expedia members.