Cheap Flights from Boston (BOS) to Winchester (WGO)

Flights from Boston (BOS) to Winchester (WGO)
Origin airport
Logan Intl.
Destination airport
Winchester Regional
Distance
434 mi

Boston to Winchester Flights

The cheapest times to fly from Boston to Winchester

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Boston to Winchester are during the month of . You can find some of the cheapest flights from Boston to Winchester with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Boston to Winchester

Sunday is one of the best days to book for cheap flights from Boston to Winchester: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Boston to Winchester

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Boston to Winchester in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Boston to Winchester flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Boston to Winchester airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional) cost?
Lock in a cheap one-way flight or cheap return flight from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional)?
The cheapest month to fly from BOS to WGO is , when demand is low. Off-peak months are typically when airlines offer lower prices between these airports.
What is the cheapest airline that flies from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional)?
Use the filters on Expedia to compare airlines and find the cheapest carrier that'll take you from BOS to WGO. Then, sort your results by "Price (lowest to highest)" to score a good deal.
How many flights per day from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional)?
There are no daily nonstop flights departing from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be soaring above the clouds in no time at all.
What day of the week has the most flights from BOS to WGO?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can vary depending on a range of factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional)?
Book a flight from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Winchester from Logan Intl. Airport (BOS)?
If you're on a direct flight from Logan Intl. Airport (BOS) to Winchester, Washington Dulles Intl. Airport (IAD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional) last-minute?
Booking your flight from BOS to WGO shortly before your journey is typically more expensive. However, if there's some wiggle room with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a BOS to WGO flight and hotel package?
You'll typically save money by booking a BOS to WGO flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one convenient place. After choosing your ideal accommodations and flights, you can add extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Logan Intl. Airport (BOS) to Winchester, VA (WGO-Winchester Regional)?
If you booked your BOS to WGO flight in the last 24 hours, you may be able to cancel or modify it without fees. Depending on the airline and the type of fare you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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Winchester nearby Airports

Washington

Boston to Washington Dulles Intl.
$109.96
*Available to One Key members.