Boston to Chesapeake Bay Flights (BOS-WAS) from $39
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Selected fares from Boston to Chesapeake Bay
The cheapest prices found with in the last 7 days for return flights were $68 and $39 for one-way flights to Chesapeake Bay for the period specified. Prices and availability are subject to change. Additional terms apply.
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Tips for booking flights from Boston to Chesapeake Bay on Travelocity
Make booking your trip from Boston to Chesapeake Bay a breeze with Travelocity's handy filters. Select whether you'd like a direct, one-stop, or multi-stop flight, only show specific airlines, and much more: It's never been so easy to tailor your journey to your preferences. Traveling with kids often means lots of luggage—so think about what baggage allowance you might need, and use the handy check-box filter to restrict your results to those with free carry-on luggage, for instance. Little ones can struggle with late-night departures or early-morning arrivals as well, so consider narrowing down your preferred arrival and departure times (yes, there's a filter for that, too) to align your travel with your family's schedule.
Flying from Boston to Chesapeake Bay: What you need to know
How to get cheap flights from Boston to Chesapeake Bay?
Booking well in advance is one of the easiest ways to cut the cost of your journey from Boston to Chesapeake Bay. In most cases, the further ahead you book, the cheaper flights tend to be. Consider traveling in the off-season, too, when prices are often lower across the board. For flights to Chesapeake Bay, the cheapest month is usually May.* Great value flights can be had on this route departing from Boston—and Travelocity's wide range of options is sure to include one that works for your family.
When is the cheapest time to travel from Boston to Chesapeake Bay?
Generally speaking, flights from Boston to Chesapeake Bay are usually cheapest in May.* In other words, that's the month to travel if you're looking to save on your adventure. Don't forget that flights are often cheaper if you book them in advance, too: Planning your travel well ahead of time is a great way to keep the cost of your family vacation low.
How far in advance can I book a flight from Boston to Chesapeake Bay?
Bookings for flights from Boston to Chesapeake Bay generally open 12 months in advance. If you're an early bird and book as soon as your date opens, that means you have a full year to sort out all the reservations for your hotel, hire car, and family-friendly vacation activities. Sometimes time's a bit tighter—but rest assured that you'll often still be able to find last-minute flights from Boston to Chesapeake Bay right up to the day that your plane is due to take off.
Is it better to book return or one-way flights from Boston to Chesapeake Bay?
Whether you book one-way or return flights is a question of personal preference. Often, booking return flights can be a cheaper option. For instance, round-trip flights from Boston to Chesapeake Bay in 2025 are available from as little as from $68, while one-way journeys start at from $39.* However, one-way flights give you the freedom to travel back from a different city or book your return leg at a later point in time, so you can shape your trip to suit you and your family.
Why should I use Travelocity to book flights from Boston to Chesapeake Bay?
When you book with Travelocity, you can choose from a large selection of airlines for your trip from Boston to Chesapeake Bay. With such an array to choose from, you're sure to find one that works for the whole family. Plus, many Travelocity flight bookings come with free cancellation—and should you need a helping hand, the customer service team is available 24/7 to assist you.
*Prices reflect current offers and availability is subject to change. Additional terms may apply.