$76 Cheap flight deals from Boston (BOS) to Winchester (CHA)
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This Weekend's Flight Deals from Boston to Winchester
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $76 One Way, $120 Round Trip from Boston to Winchester
Prices starting at $120 for return flights and $76 for one-way flights to Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Winchester economy flight packages
Caption by Hyatt Downtown Nashville
Mar 1 - Mar 4
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Jan 26, 2026
The Hermitage Hotel
Mar 3 - Mar 10
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Jun 28, 2025
1 Hotel Nashville
Mar 1 - Mar 5
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Oct 20, 2024
More About Flying To Winchester from Boston
Route Information for Flights from Boston to Winchester
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | CHA |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Winchester
Whether you want to book cheap flights from Boston to Winchester or are looking for the perfect package holiday, Orbitz is your one-stop source. Taking the stress and expense out of travel, Orbitz helps you find the best fares for Boston to Winchester flights.
Make the Most of Your Vacation
Not only does Orbitz have cheap deals for Boston to Winchester flights, we can also help you plan your vacation in advance. Why wait in lengthy lines for tickets to shows, amusement parks, and other attractions when you could be making the most of your holiday? Add activities to your flight booking for fewer hassles once you arrive in Winchester.
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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.