Cheap flights To Winchester (EEN) from $30

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Cheap Flights to Winchester from $30 One Way, $49 Round Trip

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

Wed, Dec 10 - Sat, Dec 13
MCO
Orlando Intl.
BOS
Logan Intl.
$49 Roundtrip, found 4 hours ago
$49
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Dec 10 from Orlando Intl. to Logan Intl., returning Sat, Dec 13, priced at $49 found 4 hours ago
Fri, Jan 9 - Fri, Jan 9
TPA
Tampa Intl.
BOS
Logan Intl.
$63 Roundtrip, found 7 hours ago
$63
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Fri, Jan 9 from Tampa Intl. to Logan Intl., returning Fri, Jan 9, priced at $63 found 7 hours ago
Sat, Jan 10 - Sat, Jan 10
MCO
Orlando Intl.
BDL
Bradley Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Orlando Intl. to Bradley Intl., returning Sat, Jan 10, priced at $63 found 1 day ago
Sun, Jan 18 - Sun, Jan 18
MCO
Orlando Intl.
BOS
Logan Intl.
$63 Roundtrip, found 5 hours ago
$63
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jan 18 from Orlando Intl. to Logan Intl., returning Sun, Jan 18, priced at $63 found 5 hours ago
Wed, Dec 10 - Thu, Dec 11
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$92 Roundtrip, found 2 hours ago
$92
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Dec 10 from Orlando Intl. to Portsmouth Intl., returning Thu, Dec 11, priced at $92 found 2 hours ago
Fri, Jan 9 - Mon, Jan 12
TPA
Tampa Intl.
PVD
T.F. Green
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jan 9 from Tampa Intl. to T.F. Green, returning Mon, Jan 12, priced at $102 found 1 day ago
Wed, Feb 4 - Sat, Feb 7
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Wed, Feb 4 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Feb 7, priced at $102 found 5 hours ago
Tue, Dec 9 - Tue, Dec 9
TPA
Tampa Intl.
BOS
Logan Intl.
$103 Roundtrip, found 2 days ago
$103
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Dec 9 from Tampa Intl. to Logan Intl., returning Tue, Dec 9, priced at $103 found 2 days ago
Fri, Jan 16 - Tue, Jan 20
MCO
Orlando Intl.
PVD
T.F. Green
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 16 from Orlando Intl. to T.F. Green, returning Tue, Jan 20, priced at $112 found 2 days ago
Mon, Jan 12 - Mon, Jan 12
TPA
Tampa Intl.
BDL
Bradley Intl.
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Jan 12 from Tampa Intl. to Bradley Intl., returning Mon, Jan 12, priced at $115 found 2 days ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
EEN
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, Breeze Airways, JetBlue Airways
Flight Price
$49
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 Covered Bridge Inn
2.5-star property

The Covered Bridge Inn

Dec 19 - Dec 26

7 night stay

New York (JFK) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Price was $1,062, price is now $853 per person
$853
per person
found 1 day ago
Deerfield Valley Inn
3.0-star property

Deerfield Valley Inn

Dec 26 - Dec 29

3 night stay

Sacramento (SMF) to Springfield (VSF)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $988, price is now $888 per person
$888
per person
found 15 hours ago
Mount Snow Grand Summit Resort
3.0-star property

Mount Snow Grand Summit Resort

Dec 19 - Dec 26

7 night stay

New York (JFK) to Springfield (VSF)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $2,406, price is now $1,888 per person
$1,888
per person
found 1 day ago
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Winchester

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Traveler profile updates

When flying with Orbitz, take advantage of frequent updates on your flights to Winchester. Details and updates are sent to up to six contact numbers to ensure that you are kept abreast of the latest information on Winchester flights. Frequent flyer and loyalty membership numbers may be updated within your Orbitz account profile.

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 $49 and $115 for a return trip to Winchester. Tickets one-way originating from Orlando (MCO) dipped as low as $30 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.