$75 Cheap flight deals from San Jose (SJC) to Winchester (DCA)

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This Weekend's Flight Deals from San Jose 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.

Sat, Jan 10 - Sat, Jan 17
SFO
San Francisco Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 10 from San Francisco Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jan 17, priced at $254 found 1 day ago
Sun, Jan 11 - Tue, Jan 13
SFO
San Francisco Intl.
DCA
Ronald Reagan Washington National
$260 Roundtrip, found 14 hours ago
$260
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sun, Jan 11 from San Francisco Intl. to Ronald Reagan Washington National, returning Tue, Jan 13, priced at $260 found 14 hours ago
Sat, Jan 10 - Sat, Jan 17
SJC
Norman Y. Mineta San Jose Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$451 Roundtrip, found 2 days ago
$451
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jan 10 from Norman Y. Mineta San Jose Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jan 17, priced at $451 found 2 days ago
Sun, Jan 11 - Sun, Jan 18
SJC
Norman Y. Mineta San Jose Intl.
DCA
Ronald Reagan Washington National
$460 Roundtrip, found 3 hours ago
$460
Roundtrip
found 3 hours ago
Select Alaska Airlines flight, departing Sun, Jan 11 from Norman Y. Mineta San Jose Intl. to Ronald Reagan Washington National, returning Sun, Jan 18, priced at $460 found 3 hours ago

Airfares from $75 One Way, $148 Round Trip from San Jose to Winchester

Prices starting at $148 for return flights and $75 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.

Sat, Feb 7 - Tue, Feb 10
SFO
San Francisco
DCA
Washington
$148 Roundtrip, found 3 hours ago
$148
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Feb 7 from San Francisco to Washington, returning Tue, Feb 10, priced at $148 found 3 hours ago
Wed, Feb 25 - Sat, Feb 28
SFO
San Francisco
IAD
Washington
$151 Roundtrip, found 2 days ago
$151
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Feb 25 from San Francisco to Washington, returning Sat, Feb 28, priced at $151 found 2 days ago
Thu, Apr 9 - Mon, Apr 13
SFO
San Francisco
BWI
Baltimore
$201 Roundtrip, just found
$201
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Apr 9 from San Francisco to Baltimore, returning Mon, Apr 13, priced at $201 just found
Tue, Jan 27 - Wed, Feb 4
SJC
San Jose
IAD
Washington
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Jan 27 from San Jose to Washington, returning Wed, Feb 4, priced at $251 found 1 day ago
Wed, Jan 28 - Tue, Feb 10
SJC
San Jose
DCA
Washington
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select Hawaiian Airlines flight, departing Wed, Jan 28 from San Jose to Washington, returning Tue, Feb 10, priced at $251 found 1 hour ago

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Arlo Washington DC
4.0-star property

Arlo Washington DC

9.2/10 Wonderful! (1,093 reviews)

Feb 13 - Feb 16

3 night stay

San Jose (SJC) to Baltimore (BWI)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $740, price is now $623 per person
$623
per person
just found
Great room, great location. Friendly helpful staff.

Reviewed on Dec 29, 2025

Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

9/10 Wonderful! (1,084 reviews)

Feb 13 - Feb 16

3 night stay

San Jose (SJC) to Baltimore (BWI)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $863, price is now $722 per person
$722
per person
just found
Hotel was decent but was definitely not a 5 star hotel.upon arrival no door man around to help with luggage. In fact throughout our 3 day stay there was never any staff at the front entry way! We had 4 outlets all near the bed that didn’t work. They sent someone to check it out immediately but they were never fixed. Food was decent and location excellent for seeing all the attractions in DC.

Reviewed on Sep 23, 2025

Riggs Washington DC
5.0-star property

Riggs Washington DC

9.2/10 Wonderful! (1,438 reviews)

Feb 13 - Feb 16

3 night stay

San Jose (SJC) to Baltimore (BWI)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $914, price is now $777 per person
$777
per person
just found
great location - near multiple metro stations to get anywhere; very clean

Reviewed on Jul 22, 2025

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More About Flying To Winchester from San Jose

Route Information for Flights from San Jose to Winchester

Origin Airport IATA Code
SJC
Destination Airport IATA Code
DCA
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

San Jose 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.