$32 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 $32 One Way, $63 Round Trip from Boston to Winchester
Prices starting at $63 for return flights and $32 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
Hutton Hotel
Dec 1 - Dec 5
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Jul 31, 2025
1 Hotel Nashville
Dec 1 - Dec 5
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Oct 20, 2024
The Nomad 8BR Buyout 32 Guests in Hillsboro
Nov 13 - Nov 16
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Winchester packages with premium economy flights
Hilton Garden Inn Nashville Vanderbilt
Nov 16 - Nov 20
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Aug 18, 2025
Dream Nashville, by Hyatt
Nov 16 - Nov 20
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Dec 31, 2024
Bluegreen Downtown Nashville
Nov 16 - Nov 20
Boston (BOS) to Nashville (BNA)
Nashville (BNA) to Boston (BOS)
Reviewed on Jul 13, 2025
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 | 939 mi |
Direct Flight Airlines | KLM, Icelandair, Etihad Airways, JetBlue, Southwest Airlines, SAS, Delta Air Lines, Hawaiian Airlines, Korean Air, TAP Air Portugal, Virgin Atlantic |
Earliest Flight Arrival | 10:45AM UTC |
Latest Flight Arrival | 1:44AM UTC |
Boston to 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.