Cheap flights To Winchester (DCA) from $29

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Cheap Flights to Winchester from $29 One Way, $53 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 7 - Wed, Jan 7
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$53 Roundtrip, found 1 day ago
$53
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Jan 7 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Wed, Jan 7, priced at $53 found 1 day ago
Thu, Nov 6 - Sat, Nov 8
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 18 hours ago
$60
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Thu, Nov 6 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Nov 8, priced at $60 found 18 hours ago
Thu, Jan 22 - Wed, Jan 28
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 2 hours ago
$60
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Jan 22 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jan 28, priced at $60 found 2 hours ago
Thu, Jan 29 - Thu, Jan 29
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$63 Roundtrip, found 11 hours ago
$63
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Thu, Jan 29 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jan 29, priced at $63 found 11 hours ago
Thu, Feb 19 - Thu, Feb 19
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$63 Roundtrip, found 10 hours ago
$63
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Orlando Intl. to Washington Dulles Intl., returning Thu, Feb 19, priced at $63 found 10 hours ago
Fri, Feb 20 - Fri, Feb 27
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$99 Roundtrip, found 2 days ago
$99
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Feb 20 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Fri, Feb 27, priced at $99 found 2 days ago
Thu, Jan 8 - Wed, Jan 14
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$107 Roundtrip, found 4 hours ago
$107
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Thu, Jan 8 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, Jan 14, priced at $107 found 4 hours ago
Tue, Oct 28 - Sat, Nov 1
DFW
Dallas-Fort Worth Intl.
DCA
Ronald Reagan Washington National
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Oct 28 from Dallas-Fort Worth Intl. to Ronald Reagan Washington National, returning Sat, Nov 1, priced at $120 found 6 days ago
Thu, Jan 8 - Sun, Jan 11
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Jan 8 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jan 11, priced at $132 just found
Sun, Feb 15 - Fri, Feb 20
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Feb 15 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Fri, Feb 20, priced at $137 found 1 day ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, JetBlue Airways, Southwest Airlines, American Airlines
Flight Price
$53
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Winchester economy flight packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
5.0-star property

InterContinental Washington D.C. - The Wharf by IHG

Dec 12 - Dec 15

3 night stay

Los Angeles (LAX) to Washington (DCA)

Southwest Airlines • Non-stop • Coach

Washington (DCA) to Los Angeles (LAX)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $633, price is now $302 per person
$302
per person
found 1 day ago
Hotel Washington
5.0-star property

Hotel Washington

Dec 12 - Dec 15

3 night stay

Los Angeles (LAX) to Washington (DCA)

Southwest Airlines • Non-stop • Coach

Washington (DCA) to Los Angeles (LAX)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $700, price is now $484 per person
$484
per person
found 1 day ago
The Watergate Hotel
5.0-star property

The Watergate Hotel

Dec 12 - Dec 15

3 night stay

Los Angeles (LAX) to Washington (DCA)

Southwest Airlines • Non-stop • Coach

Washington (DCA) to Los Angeles (LAX)

Frontier Airlines • Non-stop • Coach
Price was $667, price is now $468 per person
$468
per person
found 1 day ago
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Winchester premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Watergate Hotel
5.0-star property

The Watergate Hotel

8.8/10 Excellent! (1,039 reviews)

Dec 12 - Dec 14

2 night stay

San Francisco (SFO) to Washington (DCA)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $858, price is now $785 per person
$785
per person
found 7 hours ago
the service the staff the location The View

Reviewed on May 16, 2025

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Winchester

Orbitz makes it easy for you to find cheap prices for flights to Winchester. When you search for your tickets on Orbitz, you don’t have to look any further for the best Winchester flights available ever again.

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Orbitz understands that your travel plans may change. That’s why we make it simple to cancel your ticket for Winchester flights if necessary. All you have to do is contact the Orbitz Customer Service department to adjust your travel plans after booking. When you’re ready book your trip, just do a fresh search for the perfect flights to Winchester again.

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Low Prices for Winchester Flights

Orbitz has the scoop on cheap tickets and bargain airfare for flights to Winchester. You can research the best flights for your trip and make your reservations all on our website with the confidence that you’re getting a great price.

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Frequently asked questions

Which airlines fly to Winchester?
With 20 airlines operating services to Washington Dulles Intl. Airport (IAD), the entryway to Winchester, the choice is all yours. Score an awesome deal among these renowned international airlines that'll get you to this city:

  • United Airlines - 442 flights to Winchester per month
  • Air Canada - 86 flights to Winchester per month
  • Avianca - 73 flights to Winchester per month

What is the best airport to fly to in Winchester?
Winchester, VA (WGO-Winchester Regional) is the main arrival point to the city, so your trickiest decision will be the window seat or the aisle seat. Downtown Winchester is around 3 miles away and where many travelers start their adventure.
How much is a flight to Winchester?
Lots of incredible deals were had this week, with return flights to Winchester fluctuating from $53 to $137. But it was travelers flying in from Atlanta (ATL) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $29.
How to book the cheapest flight to Winchester?
Landing cheap flights to Winchester is as simple as booking your ticket with Orbitz. But if you want to make sure you're getting the best flight deals around, here are a few tips your wallet will love:

  • Depending on where you're coming from, click on the 'Nearby airports' function (located under the departure and arrival form fields). In some cases, other departure points offer more competitive fares.
  • Also, click on the 'Show flexible dates' option to view the prices on days either side of your selected departure. It's possible to pick up cheaper flight deals if your travel dates are flexible.
  • To filter your results, click on 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
  • Book your airfare as soon as you've sorted your travel dates. While it does happen occasionally, flights rarely drop in price as your date of departure nears.
  • Bundle your flights, hotels and car rental into a package deal and score great discounts. Save your money for things you're really excited about, like exploring Winchester.
  • Where possible, avoid traveling during the busy season. Airfares soar during school breaks, summer and other vacation periods like Easter and Christmas.

What is the best time to book a flight to Winchester?
Pick up a bargain and book your seats to Winchester in January. If you've missed this month, don't stress. February and August often have low airfares as well. Just make sure you don't sleep on a sale though — cheap flights come and go in an instant!
What day of the week is the cheapest to book a flight to Winchester?
When it comes to cheap flights to Winchester, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just clicks away with Orbitz.
What is the cheapest day of the week to fly to Winchester?
If you're looking for cheap flights to Winchester, depart early in the week. Orbitz data from 2020 shows Monday is the most affordable day to fly out, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to Winchester?
To book cheap flights to Winchester, you should pack your bags and depart in August. Orbitz data has found that this is generally the best month to save a bundle on your airfare. If you want to jet to Winchester in June, it's worth remembering that this is the most expensive time of year to take a trip.
Which airlines allow free cancellation?
Orbitz makes it easy to find carriers that offer flexibility. Simply click on "Filter by flexible change policies" when searching for your flights and bingo! We'll show you options that include free cancellation, no change fees and of course, the very best price.
What do I need for the flight to Winchester?
The secret to a comfortable flight is preparation. Listed below are some useful tips that'll help get you ready for your journey:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any dramas at the time of check-in, make sure that the personal info on your ticket corresponds with your government-issued ID.
  • Take some activities to keep you amused on your journey to Winchester. Books, magazines and electronic gadgets like e-readers and tablets will do the trick. Don't forget to take a refillable water bottle with you as well. Even on short flights, it's important to stay hydrated.
  • Whatever the temperature is doing outside, plane cabins can get cold. Bring a hoodie on board to stop the goose bumps.

How do I get cheap first-class/business deals to Winchester?
If you think a first or business-class ticket is beyond your grasp, you may want to think again. Here are some terrific tips to help you nab a premium flight to Winchester for less:

  • Flexibility isn't confined to yoga. Leave some room to move around your travel dates so you can snap up cheaper airfares when they crop up.
  • Plenty of low-cost carriers nowadays have outstanding business or premium-class seating that doesn't cost an arm and a leg.
  • Make the most of your airline's loyalty program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

What is the best time to go to Winchester?
There's no good or bad time to experience Winchester, though July, August and October are the most popular months. Like most places in the Northern Hemisphere, the summer commences June 20. If you'd rather hang out in a short-sleeved top than a big winter jacket, this time of year may be ideal for you. Expect average daily highs of 85 ºF and nightly lows around 65 ºF.

More to Explore

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.