$69 Cheap flight deals from San Jose (SJC) to Winchester (DCA)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Sun, Jul 13 - Mon, Jul 28
SJC
Norman Y. Mineta San Jose Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$305 Roundtrip, found 1 hour ago
$305
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Sun, Jul 13 from Norman Y. Mineta San Jose Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jul 28, priced at $305 found 1 hour ago
Sun, Jul 13 - Sat, Jul 19
SFO
San Francisco Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$345 Roundtrip, just found
$345
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Jul 13 from San Francisco Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jul 19, priced at $345 just found
Sun, Jul 13 - Thu, Jul 17
SJC
Norman Y. Mineta San Jose Intl.
DCA
Ronald Reagan Washington National
$384 Roundtrip, found 21 hours ago
$384
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Sun, Jul 13 from Norman Y. Mineta San Jose Intl. to Ronald Reagan Washington National, returning Thu, Jul 17, priced at $384 found 21 hours ago
Fri, Jul 11 - Sat, Jul 12
SFO
San Francisco Intl.
IAD
Washington Dulles Intl.
$391 Roundtrip, found 1 hour ago
$391
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Jul 11 from San Francisco Intl. to Washington Dulles Intl., returning Sat, Jul 12, priced at $391 found 1 hour ago

Airfares from $69 One Way, $162 Round Trip from San Jose to Winchester

Prices starting at $162 for return flights and $69 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.

Thu, Sep 4 - Sat, Sep 6
SJC
San Jose
IAD
Washington
$162 Roundtrip, found 1 day ago
$162
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 4 from San Jose to Washington, returning Sat, Sep 6, priced at $162 found 1 day ago
Tue, Aug 5 - Wed, Aug 13
SJC
San Jose
BWI
Baltimore
$162 Roundtrip, just found
$162
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Aug 5 from San Jose to Baltimore, returning Wed, Aug 13, priced at $162 just found
Wed, Oct 1 - Tue, Oct 7
SFO
San Francisco
IAD
Washington
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Oct 1 from San Francisco to Washington, returning Tue, Oct 7, priced at $174 found 1 day ago
Mon, Aug 25 - Sat, Aug 30
SFO
San Francisco
DCA
Washington
$175 Roundtrip, found 2 hours ago
$175
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Mon, Aug 25 from San Francisco to Washington, returning Sat, Aug 30, priced at $175 found 2 hours ago
Wed, Aug 20 - Mon, Aug 25
SFO
San Francisco
BWI
Baltimore
$177 Roundtrip, found 14 hours ago
$177
Roundtrip
found 14 hours ago
Select United flight, departing Wed, Aug 20 from San Francisco to Baltimore, returning Mon, Aug 25, priced at $177 found 14 hours ago

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
2.0-star property

Hotel Arboretum

8/10 Very Good! (792 reviews)

Aug 9 - Aug 12

3 night stay

San Jose (SJC) to Washington (DCA)

Southwest Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
parking so expensive !! Rooms are not clean !! bathroom tub is so bad

Reviewed on Jul 1, 2025

Sheraton Pentagon City Hotel
3.5-star property

Sheraton Pentagon City Hotel

8.4/10 Very Good! (2,282 reviews)

Aug 9 - Aug 12

3 night stay

San Jose (SJC) to Washington (DCA)

Southwest Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Staff was ALL helpful and courteous...superb! Food was exceptional! One of our best stays ever!

Reviewed on Jun 22, 2025

Omni Shoreham Hotel
4.0-star property

Omni Shoreham Hotel

8.8/10 Excellent! (1,941 reviews)

Aug 9 - Aug 12

3 night stay

San Jose (SJC) to Washington (DCA)

Southwest Airlines • Non-stop roundtrip • Coach
per person
found 1 day ago
Beautiful lobby, and gardens. Only issue was our bathroom was very small. We expected a larger bath like their other resorts we have stayed with.

Reviewed on Jul 6, 2025

Don't see what you're looking for?
See all available trips from San Jose to Winchester
View all trips

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
2436 mi
Direct Flight Airlines
Alaska Airlines, Fiji Airways, Qantas, Hawaiian Airlines, Virgin Australia, Air New Zealand, United Airlines
Earliest Flight Arrival
6:46PM UTC
Latest Flight Arrival
4:27AM UTC

San Jose to Winchester

If you have been putting off a well-deserved vacation due to a tight budget, now is the time to visit Orbitz.com. We offer you huge savings on San Jose to Winchester flights, great hotel rooms, and stellar vacation packages. Let Orbitz show you how to cheaply plan the perfect trip.

Guaranteed low prices on flights from San Jose to Winchester

Low fares, discounted rates, great deals, and special promotions—all of these can be found through Orbitz. Get cheap fares on San Jose to Winchester flights and amazing deals on luxury hotels. You can even accumulate loyalty or frequent flyer miles or points on qualifying flights from San Jose to Winchester so you can earn flight rewards on your favorite airlines.

Mobile planning for flights from San Jose to Winchester

Worried about unexpected flight delays or other travel disruptions on your San Jose to Winchester flights? You can opt to receive free alerts sent to you and six of your contacts via email, voicemail, or text. The Orbitz mobile app also lets you access up-to-date flight information from your iPhone, iPad, and mobile Android devices. Our mobile technology let you check baggage claim and gate details, view your itinerary for your flights from San Jose to Winchester, and book exclusive hotel deals—even on the same day.

Take advantage of low fares on San Jose to Winchester flights and vacation packages

Orbitz has the best prices available on flights from San Jose to Winchester. Take advantage of our low fare sales and discounts and begin to plan your next trip. We also give you great savings on hotels, car rentals, and vacation packages.

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.