Cheap flights To Winchester (EEN) from $99

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Winchester from $99 One Way, $197 Round Trip

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

Wed, Oct 22 - Tue, Oct 28
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Alaska Airlines flight, departing Wed, Oct 22 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Oct 28, priced at $197 just found
Tue, Sep 30 - Thu, Oct 2
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Alaska Airlines flight, departing Tue, Sep 30 from Seattle - Tacoma Intl. to Logan Intl., returning Thu, Oct 2, priced at $200 just found
Tue, Sep 16 - Tue, Sep 23
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$207 Roundtrip, found 3 hours ago
$207
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Sep 23, priced at $207 found 3 hours ago
Wed, Nov 5 - Wed, Nov 5
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$213 Roundtrip, found 10 hours ago
$213
Roundtrip
found 10 hours ago
Select Alaska Airlines flight, departing Wed, Nov 5 from Seattle - Tacoma Intl. to Logan Intl., returning Wed, Nov 5, priced at $213 found 10 hours ago
Fri, Sep 5 - Mon, Sep 8
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$217 Roundtrip, just found
$217
Roundtrip
just found
Select Alaska Airlines flight, departing Fri, Sep 5 from Seattle - Tacoma Intl. to Logan Intl., returning Mon, Sep 8, priced at $217 just found
Wed, Oct 1 - Tue, Oct 7
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$217 Roundtrip, found 13 hours ago
$217
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, Oct 1 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Oct 7, priced at $217 found 13 hours ago
Sat, Nov 8 - Sat, Nov 15
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$218 Roundtrip, found 16 hours ago
$218
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Sat, Nov 8 from Seattle - Tacoma Intl. to Logan Intl., returning Sat, Nov 15, priced at $218 found 16 hours ago
Wed, Sep 24 - Sat, Sep 27
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$221 Roundtrip, found 2 days ago
$221
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 24 from Seattle - Tacoma Intl. to Logan Intl., returning Sat, Sep 27, priced at $221 found 2 days ago
Wed, Oct 1 - Tue, Oct 7
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$237 Roundtrip, found 13 hours ago
$237
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Wed, Oct 1 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Oct 7, priced at $237 found 13 hours ago
Wed, Sep 10 - Tue, Sep 16
SEA
Seattle - Tacoma Intl.
BOS
Logan Intl.
$240 Roundtrip, found 1 day ago
$240
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 10 from Seattle - Tacoma Intl. to Logan Intl., returning Tue, Sep 16, priced at $240 found 1 day ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
EEN
Number of Airlines Serving
Airlines
Alaska Airlines, JetBlue Airways, Delta, United, American Airlines, Southwest Airlines, Sun Country Airlines
Flight Price
$197
Earliest Departing Flight
Latest Departing Flight

Winchester

Finding cheap flights to Winchester is easy when you have Orbitz at your fingertips. Not only does Orbitz offer great deals on Winchester flights, but we also include some special extras to make booking a breeze. Just check out our:

Mobile Site and Apps

With Orbitz’s mobile site, m.orbitz.com, you can book your flights to Winchester through your smartphone or tablet’s Web browser. Plus, our free downloadable apps for Android and iPhone mean it’s just a simple click to access your flight updates and alerts. You can even book exclusive mobile-only deals on hotels to go with your flights to Winchester—even on the same day.

Pick and Choose or Book Full Vacation Packages

Don’t just be satisfied with great deals on Winchester flights—go for the full package! With Orbitz, you can also find fantastic savings on the perfect hotel, car rental, cruise, and even activities, so you don’t waste your trip waiting in line but have the time to enjoy your trip. Pick and choose the add-ons you need, or book an entire vacation package for greater overall discounts.

Rewards That Are Miles Better

Booking directly with an airline earns you air miles or points, and you can get those same rewards with booking on Orbitz too. When you book qualifying flights to Winchester with Orbitz, just add in your frequent flyer number during your online booking and your details will be sent to your program.

Great Deals Every Day

Add in our extra savings on packages, free nights, and other discounts, and you know you are in good hands.

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 $197 and $240 for a return trip to Winchester. Tickets one-way originating from Seattle (SEA) dipped as low as $99 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.

Nearby

Flights To

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.