Cheap flights To Winchester (EEN) from $59

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Cheap Flights to Winchester from $59 One Way, $117 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Dec 5 - Mon, Dec 7
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Dec 5 from Ronald Reagan Washington National to Logan Intl., returning Mon, Dec 7, priced at $117 found 5 hours ago
Sat, Nov 14 - Mon, Nov 16
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$119 Roundtrip, found 8 hours ago
$119
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 14 from Ronald Reagan Washington National to Logan Intl., returning Mon, Nov 16, priced at $119 found 8 hours ago
Fri, Dec 11 - Sun, Dec 13
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$144 Roundtrip, found 1 day ago
$144
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Dec 11 from Ronald Reagan Washington National to Logan Intl., returning Sun, Dec 13, priced at $144 found 1 day ago
Sat, Nov 14 - Mon, Nov 16
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$149 Roundtrip, found 8 hours ago
$149
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 14 from Ronald Reagan Washington National to Logan Intl., returning Mon, Nov 16, priced at $149 found 8 hours ago
Sat, Nov 14 - Mon, Nov 16
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$154 Roundtrip, found 8 hours ago
$154
Roundtrip
found 8 hours ago
Select JetBlue Airways flight, departing Sat, Nov 14 from Ronald Reagan Washington National to Logan Intl., returning Mon, Nov 16, priced at $154 found 8 hours ago
Sat, Nov 14 - Mon, Nov 16
DCA
Ronald Reagan Washington National
BOS
Logan Intl.
$159 Roundtrip, found 8 hours ago
$159
Roundtrip
found 8 hours ago
Select Delta flight, departing Sat, Nov 14 from Ronald Reagan Washington National to Logan Intl., returning Mon, Nov 16, priced at $159 found 8 hours ago
Tue, Oct 27 - Sat, Oct 31
DCA
Ronald Reagan Washington National
PVD
T.F. Green
$163 Roundtrip, found 3 days ago
$163
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Oct 27 from Ronald Reagan Washington National to T.F. Green, returning Sat, Oct 31, priced at $163 found 3 days ago
Tue, Oct 27 - Sat, Oct 31
DCA
Ronald Reagan Washington National
PVD
T.F. Green
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 27 from Ronald Reagan Washington National to T.F. Green, returning Sat, Oct 31, priced at $164 found 3 days ago
Thu, Oct 29 - Mon, Nov 2
DCA
Ronald Reagan Washington National
PVD
T.F. Green
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Thu, Oct 29 from Ronald Reagan Washington National to T.F. Green, returning Mon, Nov 2, priced at $167 found 2 days ago
Sat, Nov 14 - Mon, Nov 16
DCA
Ronald Reagan Washington National
PVD
T.F. Green
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Nov 14 from Ronald Reagan Washington National to T.F. Green, returning Mon, Nov 16, priced at $170 found 5 days ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
EEN
Number of Airlines Serving
Airlines
JetBlue Airways, American Airlines, Southwest Airlines, Delta
Flight Price
$117
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
2.0-star property

Deerfield Valley Inn

Oct 23 - Oct 25

2 night stay

Dallas (DFW) to Springfield (VSF)

American Airlines • Non-stop • Coach

Springfield (VSF) to Dallas (DFW)

Southwest Airlines • Non-stop • Coach
Price was $684, price is now $629 per person
$629
per person
found 6 hours ago
Sinclair Inn Bed and Breakfast
4.0-star property

Sinclair Inn Bed and Breakfast

Oct 26 - Oct 29

3 night stay

Austin (AUS) to Springfield (VSF)

Delta • Non-stop roundtrip • Coach
Price was $1,371, price is now $1,166 per person
$1,166
per person
found 19 hours ago
Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5-star property

Holiday Inn Express Hotel & Suites Brattleboro by IHG

Oct 22 - Oct 26

4 night stay

Ontario Intl. Airport (ONT) to Springfield (VSF)

Delta • Coach

Springfield (VSF) to Ontario Intl. Airport (ONT)

Southwest Airlines • Coach
Price was $1,033, price is now $944 per person
$944
per person
found 11 hours ago
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Winchester

End your search for discount fares on flights to Winchester. Orbitz has all the best prices on Winchester flights. With Orbitz, you can expect:

Cheap Deals on Flights to Winchester

We offer big discounts and last-minute savings on Winchester flights. We make it easy for you to research, plan, and book your flight to Winchester — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

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Get alerts, updates, or book your Winchester flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Winchester flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Winchester flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Winchester flights to the actual booking. If you want to cancel your flight to Winchester, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Winchester with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

Frequently asked questions

Which airlines fly to Winchester?
With 20 airlines to take your pick of, finding the right flight that matches your budget and plans will be easy. Logan Intl. Airport (BOS) is the entrance point to Winchester and where you'll likely be landing. These leading international airlines are ready and waiting to take you there:

  • JetBlue - 175 flights to Winchester per month
  • Delta - 158 flights to Winchester per month
  • Air Canada - 151 flights to Winchester per month

How much is a flight to Winchester?
Last week, prices hovered between $117 and $170 for a return trip to Winchester. Tickets one-way originating from Washington (DCA) dipped as low as $59 during the same time period.
How to book the cheapest flight to Winchester?
Snapping up cheap flights to Winchester is as easy as booking with Orbitz. But if you're eager to make sure you're nabbing the best flight deals around, here are some suggestions your wallet will love:

  • Departing from or arriving at nearby airports can often save you money. Enter your preferred departure and arrival airports. Next, click on the 'Nearby airports' function below the form fields to see what your options are.
  • If your plans aren't etched in stone, click on the 'Show flexible dates' option to view the flight deals across different departure dates. You may find a cheaper fare.
  • Select 'Show options' to fine tune your search results. You can choose your preferred airline and seating class here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • Reserve your airfare as soon as you've worked out your travel dates. While you can get lucky once in a while, flights rarely get more affordable as your date of departure nears.
  • Make greater savings on your adventure by bundling your flights, hotels and car rentals into one handy package. Your bank account will thank you for it.
  • If possible, don't travel in high seasons. Airfares surge during summer, school breaks and around other vacation times like Easter and Thanksgiving.

What is the best time to book a flight to Winchester?
If you can, purchase your flights to Winchester in January. This is the best month to get low airfares, closely followed by February and August. With a bit of patience and planning, you're sure to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Winchester?
To score a rewarding flight deal, book on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days of the week to purchase airfares to Winchester.
What is the cheapest day of the week to fly to Winchester?
Look into departing early in the week to get cheap flights to Winchester. Orbitz data from 2020 indicates Monday is normally the cheapest day to take off, followed by Tuesday. Saturday was found to have the most expensive airfares. This is probably because most passengers prefer to start their trip on a weekend.
What is the cheapest month to fly to Winchester?
To land cheap flights to Winchester, you should leave in August. If saving money on your ticket is your main concern, Orbitz data has found that this is generally the best month to travel. June is when airfares are the least affordable.
Which airlines allow free cancellation?
If you suspect your travel plans could change, Orbitz can help you find a flexible fare. All you have to do is select "Filter by flexible change policies" when searching for your flights. We'll show you all the airlines that include free cancellation within 24 hours and no change fees — along with our famous low prices.
What do I need for the flight to Winchester?
There's nothing more enjoyable than jetting to a new destination, but it's good to be prepared. The following practical tips will help get your journey off to a great start:

  • Your travel documents are the most important things you'll need to carry with you on your flight. To avoid any delays at the time of check-in, make sure that the information displayed on your ticket is the same as on your government-issued photo ID.
  • Take some activities to keep you entertained on your trip to Winchester. Magazines, books and electronic gadgets like e-readers and tablets should do the trick. Make sure you take a bottle of water as well. Even on a short flight, it's important to remain well-hydrated.
  • It can get chilly on the plane. If you don't like the thought of shivering your way through the flight, dress in layers.

How do I get cheap first-class/business deals to Winchester?
Experienced travelers have a talent for finding business or first-class fares to Winchester without the sky-high price tag. Follow their example with these useful tips:

  • Be flexible with your travel dates and wait for sales on business or first-class airfares.
  • Search for a budget airline that offers seats in business class. They often come with more space and a glass of bubbly — but at a more affordable price.
  • Take advantage of your airline's loyalty scheme and use points to upgrade your seat. You can also bid for an upgrade in online auctions.

What is the best time to go to Winchester?
You'll have fun whatever time of year you visit Winchester, but January, June and September are the most popular months. Like to fill up your itinerary with warm-weather activities? Plan your trip around June 20. This is when the summer season kicks off in the Northern Hemisphere. Expect the mercury to drift between 55 ºF and 80 ºF during this time of year.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.