Cheap flights To Winchester (DCA) from $28

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Cheap Flights to Winchester from $28 One Way, $56 Round Trip

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

Tue, Oct 20 - Wed, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 12 hours ago
$56
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 21, priced at $56 found 12 hours ago
Mon, Oct 26 - Wed, Nov 4
FLL
Fort Lauderdale - Hollywood Intl.
IAD
Washington Dulles Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Oct 26 from Fort Lauderdale - Hollywood Intl. to Washington Dulles Intl., returning Wed, Nov 4, priced at $68 found 1 hour ago
Wed, Aug 12 - Wed, Aug 19
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$77 Roundtrip, found 6 days ago
$77
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 19, priced at $77 found 6 days ago
Tue, Aug 4 - Tue, Aug 11
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$78 Roundtrip, found 3 days ago
$78
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Aug 11, priced at $78 found 3 days ago
Tue, Sep 22 - Wed, Sep 23
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 4 days ago
$82
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 23, priced at $82 found 4 days ago
Wed, Aug 5 - Mon, Aug 10
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$87 Roundtrip, found 3 days ago
$87
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 5 from Orlando Intl. to Washington Dulles Intl., returning Mon, Aug 10, priced at $87 found 3 days ago
Wed, Oct 14 - Sat, Oct 17
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$92 Roundtrip, found 8 hours ago
$92
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Sat, Oct 17, priced at $92 found 8 hours ago
Tue, Oct 20 - Wed, Oct 21
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 20 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Oct 21, priced at $92 found 3 days ago
Mon, Aug 3 - Mon, Aug 3
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$115 Roundtrip, found 16 hours ago
$115
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 3 from Orlando Intl. to Washington Dulles Intl., returning Mon, Aug 3, priced at $115 found 16 hours ago
Tue, Sep 29 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$169 Roundtrip, found 17 hours ago
$169
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Sep 29 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Tue, Oct 6, priced at $169 found 17 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, JetBlue Airways, United
Flight Price
$56
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.
Historic Inns of Annapolis
3.5-star property

Historic Inns of Annapolis

Jul 17 - Jul 20

3 night stay

Charlotte (CLT) to Baltimore (BWI)

Frontier Airlines • Roundtrip • Coach
Price was $543, price is now $380 per person
$380
per person
found 3 hours ago
Salamander Washington DC
5.0-star property

Salamander Washington DC

Aug 1 - Aug 4

3 night stay

Atlanta (ATL) to Baltimore (BWI)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $875, price is now $611 per person
$611
per person
found 1 day ago
Eurostars Saint Gregory Dupont Circle Georgetown
4.0-star property

Eurostars Saint Gregory Dupont Circle Georgetown

Jul 20 - Jul 23

3 night stay

Atlanta (ATL) to Baltimore (BWI)

Delta • Coach

Baltimore (BWI) to Atlanta (ATL)

Frontier Airlines • Coach
Save 100% on your flight
Price was $786, price is now $570 per person
$570
per person
found 1 day ago
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See all available trips from Charlotte to Winchester
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Winchester business class flight packages

Price found within the past 48 hours. Click for updated prices.
Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

9/10 Wonderful! (1,189 reviews)

Jul 16 - Jul 19

3 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,256, price is now $1,113 per person
$1,113
per person
found 1 day ago
Very good location where you can walk to all the tourist areas and enjoy fine restaurants nearby.

Reviewed on May 26, 2026

Salamander Washington DC
5.0-star property

Salamander Washington DC

9.4/10 Exceptional! (1,099 reviews)

Jul 16 - Jul 19

3 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,565, price is now $1,347 per person
$1,347
per person
found 1 day ago
I should have been warned that the entire view from my window would be a tear-down of a building. Even a brick wall would have been better. Not the tranquil view I wanted for my birthday. So I kept the curtains closed. The “in room dining” line just rang. No answer,

Reviewed on Nov 16, 2025

Placemakr Buzzard Point
4.0-star property

Placemakr Buzzard Point

9.2/10 Wonderful! (187 reviews)

Jul 16 - Jul 19

3 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,406, price is now $1,233 per person
$1,233
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Los Angeles to Winchester
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Winchester

Snag some “suite” deals when you add cheap hotel rooms to Winchester flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

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Fun for All

While shopping Orbitz sales on Winchester flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Winchester flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Winchester. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $56 to $169. But it was travelers flying in from Atlanta (ATL) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $28.
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.