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.

Fri, Jun 5 - Mon, Jun 8
ATL
Hartsfield-Jackson Atlanta Intl.
IAD
Washington Dulles Intl.
$56 Roundtrip, found 6 hours ago
$56
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, Jun 5 from Hartsfield-Jackson Atlanta Intl. to Washington Dulles Intl., returning Mon, Jun 8, priced at $56 found 6 hours ago
Wed, May 27 - Thu, May 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, May 27 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, May 28, priced at $56 just found
Wed, Aug 12 - Tue, Aug 18
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, found 1 day ago
$68
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 18, priced at $68 found 1 day ago
Mon, Jun 8 - Mon, Jun 8
DFW
Dallas-Fort Worth Intl.
IAD
Washington Dulles Intl.
$92 Roundtrip, found 4 days ago
$92
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Mon, Jun 8 from Dallas-Fort Worth Intl. to Washington Dulles Intl., returning Mon, Jun 8, priced at $92 found 4 days ago
Fri, Aug 21 - Mon, Aug 24
ATL
Hartsfield-Jackson Atlanta Intl.
DCA
Ronald Reagan Washington National
$169 Roundtrip, found 2 hours ago
$169
Roundtrip
found 2 hours ago
Select Delta flight, departing Fri, Aug 21 from Hartsfield-Jackson Atlanta Intl. to Ronald Reagan Washington National, returning Mon, Aug 24, priced at $169 found 2 hours ago
Sat, May 23 - Wed, May 27
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, May 23 from Los Angeles Intl. to Ronald Reagan Washington National, returning Wed, May 27, priced at $190 found 1 day ago
Sat, May 23 - Tue, Jun 9
SFO
San Francisco Intl.
IAD
Washington Dulles Intl.
$190 Roundtrip, found 5 days ago
$190
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 23 from San Francisco Intl. to Washington Dulles Intl., returning Tue, Jun 9, priced at $190 found 5 days ago
Wed, May 20 - Wed, May 27
LAX
Los Angeles Intl.
IAD
Washington Dulles Intl.
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, May 20 from Los Angeles Intl. to Washington Dulles Intl., returning Wed, May 27, priced at $190 found 2 days ago
Tue, Sep 15 - Tue, Sep 22
SEA
Seattle - Tacoma Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$197 Roundtrip, found 17 hours ago
$197
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Tue, Sep 15 from Seattle - Tacoma Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 22, priced at $197 found 17 hours ago
Tue, Aug 18 - Tue, Aug 25
DAL
Love Field
DCA
Ronald Reagan Washington National
$199 Roundtrip, found 11 hours ago
$199
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Tue, Aug 18 from Love Field to Ronald Reagan Washington National, returning Tue, Aug 25, priced at $199 found 11 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, American Airlines, Southwest Airlines, Delta
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.
Kellogg Conference Hotel at Gallaudet University
3.0-star property

Kellogg Conference Hotel at Gallaudet University

Jun 24 - Jun 29

5 night stay

Boston (BOS) to Baltimore (BWI)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $848, price is now $515 per person
$515
per person
found 1 day ago
DoubleTree by Hilton Washington DC - Crystal City
4.0-star property

DoubleTree by Hilton Washington DC - Crystal City

Jun 9 - Jun 16

7 night stay

Boston (BOS) to Baltimore (BWI)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,344, price is now $895 per person
$895
per person
found 24 hours ago
Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

Jun 8 - Jun 12

4 night stay

Boston (BOS) to Baltimore (BWI)

JetBlue Airways • Coach

Baltimore (BWI) to Boston (BOS)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,572, price is now $1,087 per person
$1,087
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.
Residence Inn by Marriott Alexandria Old Town South at Carlyle
3.0-star property

Residence Inn by Marriott Alexandria Old Town South at Carlyle

8.8/10 Excellent! (1,001 reviews)

Jun 10 - Jun 16

6 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,338, price is now $959 per person
$959
per person
found 7 hours ago
staff was friendly and helpful, good healthy choices for free breakfast

Reviewed on Jan 15, 2026

Riggs Washington DC
5.0-star property

Riggs Washington DC

9.4/10 Exceptional! (1,441 reviews)

Jun 10 - Jun 16

6 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,482, price is now $1,872 per person
$1,872
per person
found 7 hours ago
great location - near multiple metro stations to get anywhere; very clean

Reviewed on Jul 22, 2025

The Westin Alexandria Old Town
4.0-star property

The Westin Alexandria Old Town

9.2/10 Wonderful! (1,008 reviews)

Jun 10 - Jun 16

6 night stay

Los Angeles (LAX) to Baltimore (BWI)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Price was $1,479, price is now $1,150 per person
$1,150
per person
found 7 hours ago
I have stayed at many Westin hotels and I have always considered them excellent in every regard. Super value for your travel dollars! Gotta say, I was disappointed in the Westin Alexandria -- it was not up to Westin standards. If you order room service, it comes in to-go boxes, in a bag, like Food-to-Go. Plastic wear. And the menu was not at all what it should be. I ordered a Heineken that never showed up. For breakfast my mushroom & onion omelette was peppers and onions. Now I like peppers, and so it was not a problem, but .... write the damn order down so people can read it. Seriously. The in-room dining set the tone. Then, throughout the night, the toilet kept bubbling. Not sure what was bubbling, but it was bubbling up. That's reassuring and helpful for a restful sleep. I had no issues with any of the people I met. Front desk was super, parking was fast and easy, food-delivery were extremely nice. So when corporate reads this, don't go yelling at any of them. They were wonderful. But fix the other stuff. You are better than this.

Reviewed on Jan 12, 2025

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Winchester

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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 $56 to $199. 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.