Cheap flights To Winchester (EEN) from $76

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Cheap Flights to Winchester from $76 One Way, $155 Round Trip

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

Mon, Jan 26 - Tue, Feb 3
BOS
Logan Intl.
LEB
Lebanon Municipal
$155 Roundtrip, found 4 days ago
$155
Roundtrip
found 4 days ago
Select Cape Air flight, departing Mon, Jan 26 from Logan Intl. to Lebanon Municipal, returning Tue, Feb 3, priced at $155 found 4 days ago
Wed, Dec 24 - Sun, Dec 28
BOS
Logan Intl.
LEB
Lebanon Municipal
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Cape Air flight, departing Wed, Dec 24 from Logan Intl. to Lebanon Municipal, returning Sun, Dec 28, priced at $157 found 1 day ago
Tue, Jan 6 - Sat, Jan 10
BOS
Logan Intl.
LEB
Lebanon Municipal
$157 Roundtrip, found 2 hours ago
$157
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Tue, Jan 6 from Logan Intl. to Lebanon Municipal, returning Sat, Jan 10, priced at $157 found 2 hours ago
Thu, Dec 25 - Fri, Dec 26
BOS
Logan Intl.
LEB
Lebanon Municipal
$159 Roundtrip, found 10 hours ago
$159
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Thu, Dec 25 from Logan Intl. to Lebanon Municipal, returning Fri, Dec 26, priced at $159 found 10 hours ago
Sat, Jan 17 - Sun, Jan 18
BOS
Logan Intl.
LEB
Lebanon Municipal
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Cape Air flight, departing Sat, Jan 17 from Logan Intl. to Lebanon Municipal, returning Sun, Jan 18, priced at $159 found 5 days ago
Fri, Jan 16 - Sun, Jan 18
BOS
Logan Intl.
LEB
Lebanon Municipal
$165 Roundtrip, found 17 hours ago
$165
Roundtrip
found 17 hours ago
Select Cape Air flight, departing Fri, Jan 16 from Logan Intl. to Lebanon Municipal, returning Sun, Jan 18, priced at $165 found 17 hours ago
Tue, Jan 6 - Sat, Jan 10
BOS
Logan Intl.
LEB
Lebanon Municipal
$168 Roundtrip, found 2 hours ago
$168
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Tue, Jan 6 from Logan Intl. to Lebanon Municipal, returning Sat, Jan 10, priced at $168 found 2 hours ago
Tue, Jan 6 - Wed, Jan 7
BOS
Logan Intl.
LEB
Lebanon Municipal
$169 Roundtrip, found 5 days ago
$169
Roundtrip
found 5 days ago
Select Cape Air flight, departing Tue, Jan 6 from Logan Intl. to Lebanon Municipal, returning Wed, Jan 7, priced at $169 found 5 days ago
Mon, Jan 12 - Thu, Jan 22
BOS
Logan Intl.
BDL
Bradley Intl.
$184 Roundtrip, found 3 days ago
$184
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Mon, Jan 12 from Logan Intl. to Bradley Intl., returning Thu, Jan 22, priced at $184 found 3 days ago
Thu, Jan 8 - Fri, Jan 16
BOS
Logan Intl.
PVD
T.F. Green
$213 Roundtrip, found 12 hours ago
$213
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, Jan 8 from Logan Intl. to T.F. Green, returning Fri, Jan 16, priced at $213 found 12 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
EEN
Number of Airlines Serving
Airlines
Cape Air, JetBlue Airways
Flight Price
$155
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.
The Shire Woodstock
3.0-star property

The Shire Woodstock

Feb 13 - Feb 17

4 night stay

West Palm Beach (PBI) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to West Palm Beach (PBI)

Cape Air • Non-stop • Coach
Price was $816, price is now $816 per person
$816
per person
found 1 day ago
Jackson Gore Village
3.0-star property

Jackson Gore Village

Feb 13 - Feb 17

4 night stay

West Palm Beach (PBI) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to West Palm Beach (PBI)

Cape Air • Non-stop • Coach
Price was $2,887, price is now $2,593 per person
$2,593
per person
found 1 day ago
Lincoln Inn & Gallery
2.0-star property

Lincoln Inn & Gallery

Feb 13 - Feb 17

4 night stay

West Palm Beach (PBI) to Springfield (VSF)

JetBlue Airways • Non-stop • Coach

Springfield (VSF) to West Palm Beach (PBI)

Cape Air • Non-stop • Coach
Price was $1,017, price is now $972 per person
$972
per person
found 1 day ago
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Winchester

Reach your destination without breaking your budget by booking your flights to Winchester using Orbitz. We offer access to all of the best discounts on airfare, travel accommodations and even car rentals. Planning your trip and saving money are easier with Orbitz.

Get Discount Rates On Your Winchester Flight

Whether planning ahead or deciding to book your trip at the last minute, Orbitz will provide the lowest rates on Winchester flights. Using our free mobile phone apps will make you privy to a number of discounts that are unique to mobile phone users. These are perfect for harried travelers who want to find deals that they can qualify for on the same day.

Make Orbitz Your Official Travel Planner

Orbitz can be used for much more than comparing and booking a discount flight to Winchester. We also offer a variety of resources for securing the ideal travel accommodations while staying on budget. Travel tips, hotel reviews, customized suggestions and even detailed images can all be accessed through your mobile phone.

Build A Comprehensive Travel Itinerary

In addition to booking a low cost flight to Winchester, you can learn about the best places to visit, the best hotels to stay in and the preferred times for traveling. When you use Orbitz mobile phone apps you can also share your travel itineraries with friends and family members, all with just a few quick taps.

Using Orbitz to secure your Winchester flights can save you money and time. Perfect for both the early travel planner and the last minute journey: Orbitz offers phenomenal customer service and unbeatable convenience.

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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 $155 and $213 for a return trip to Winchester. Tickets one-way originating from Boston (BOS) dipped as low as $76 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.