Cheap Flight Deals to Winchester VA from CA $192
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How to find cheap flights to Winchester?
The cheapest prices found with in the last 7 days for return flights were CA $219 and CA $192 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| BOS | Baltimore | June 30 to July 8 | CA $219 |
| BOS | Washington | September 10 to September 11 | CA $258 |
| FLL | Baltimore | July 29 to August 4 | CA $272 |
| ATL | Baltimore | September 7 to September 12 | CA $367 |
| BOS | Chantilly | July 24 to July 26 | CA $435 |
| LAX | Baltimore | August 6 to August 11 | CA $472 |
| LAX | Washington | September 11 to September 18 | CA $479 |
| ATL | Washington | July 2 to July 6 | CA $480 |
| FLL | Chantilly | August 9 to August 11 | CA $484 |
| CLT | Baltimore | August 6 to August 10 | CA $509 |
| SFO | Chantilly | September 2 to September 7 | CA $554 |
| DFW | Washington | July 30 to August 3 | CA $632 |
| LAX | Chantilly | July 23 to July 28 | CA $675 |
| DFW | Chantilly | August 13 to August 18 | CA $971 |
| FCO | Baltimore | August 27 to September 3 | CA $1,184 |
| Origin | Destination | Travel dates | Flights from* |
|---|---|---|---|
| FLL | Washington | June 13 to June 15 | CA $341 |
| BOS | Washington | June 12 to June 16 | CA $556 |
| MCO | Washington | June 13 to June 15 | CA $628 |
| LAX | Washington | June 13 to June 16 | CA $823 |
| BOS | Baltimore | June 13 to June 20 | CA $871 |
| DEN | Washington | June 12 to June 15 | CA $948 |
| SFO | Washington | June 13 to June 16 | CA $997 |
| LAX | Chantilly | June 13 to June 16 | CA $1,051 |
| DFW | Washington | June 14 to June 18 | CA $1,384 |
| DFW | Chantilly | June 12 to June 14 | CA $1,592 |
| LAX | Baltimore | June 14 to June 15 | CA $1,627 |
| ATL | Baltimore | June 13 to August 12 | CA $1,732 |
| SFO | Chantilly | June 13 to June 15 | CA $1,784 |
| DFW | Baltimore | June 14 to June 17 | CA $1,873 |
| ATL | Chantilly | June 13 to June 20 | CA $2,306 |
Your guide to flights to Winchester, VA
JetBlue Airways, Porter Airlines, Alaska Airlines fly to Winchester, so use Travelocity to search, find, and compare some truly tempting deals from the 4 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winchester VA currently costs between CA $219 and CA $2,306. Prices vary, but for the best fares, travel in September when prices are at their lowest.
Top tips for finding cheap flights to Winchester
The cheapest flight for a round trip to Winchester is currently CA $219. When you search for flights to Winchester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winchester for nearby days. The cheapest month to travel to Winchester is August from our list of deals available.
But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.
How to cancel flights to Winchester
We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.
Why you should book your flight to Winchester with Travelocity
We have top deals on plane tickets even for last minute flights to Winchester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winchester for less.
Find The Perfect Hotel For After Your Flight
Amazing Place to Stay After Flight to Winchester
Motel 6 Winchester, VA
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
"Was a nice stop no complaints. It was as expected at a good value"
Reviewed on Jun 7, 2026
Twi-Lite Inn
"Clean, quiet, good location."
Reviewed on May 25, 2026
Royal Inn Motel
"It’s a roadside motel. Extremely cheap. For the price- it was excellent. Beds comfortable enough. Not enough towels. No toiletries besides soap. NO COFFEE MAKER. That was strange. BUT the room was big and had fridge and microwave. Overall very happy."
Reviewed on Dec 23, 2020
Luxury Hotels in Winchester
Motel 6 Winchester, VA
"very pet friendly, large area for dogs, well lighted parking"
Reviewed on Jun 9, 2026
Travelodge by Wyndham Winchester
"Was a nice stop no complaints. It was as expected at a good value"
Reviewed on Jun 7, 2026
Wayside Inn
"Clean, well-maintained, delicious food, hot shower!"
Reviewed on Jun 7, 2026
Hotel Strasburg
"The place was closed and looks like it has been for quite sometime. The outside was run down and litter all over. We drove 5 hours to get there and even had a confirmation number from hotel. Com. Very disappointed!!!!!!"
Reviewed on Oct 5, 2020
Family Friendly Hotels in Winchester
Country Inn & Suites by Radisson, Winchester, VA
"Room very clean. Breakfast was nice. Please consider adding instant grits to menu."
Reviewed on Jun 10, 2026
Fairfield Inn & Suites Strasburg Shenandoah Valley
"Standard hotel. Neither excellent nor lacking."
Reviewed on Jun 7, 2026
Quality Inn Winchester
"Very nice affordable hotel right off 81."
Reviewed on Jun 10, 2026
Hampton Inn Front Royal
"Excellent swimming pool, a little cool. Room was very spacious and clean."
Reviewed on Jun 9, 2026
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Need a car after flight to Winchester?
Economy
Compact
Midsize
SUV
Frequently asked questions
Plane Tickets To Winchester
Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.
When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winchester today!
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