Cheap flights To Winchester (DCA) from $28

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

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.

Thu, Apr 30 - Sat, May 2
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Washington Dulles Intl., returning Sat, May 2, priced at $56 found 2 hours ago
Fri, May 8 - Sun, May 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 6 hours ago
$56
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 10, priced at $56 found 6 hours ago
Thu, May 7 - Fri, May 8
ORD
O'Hare Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$81 Roundtrip, found 3 days ago
$81
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 7 from O'Hare Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, May 8, priced at $81 found 3 days ago
Tue, Mar 10 - Tue, Mar 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 5 days ago
$87
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Mar 10 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Mar 10, priced at $87 found 5 days ago
Mon, Mar 30 - Mon, Apr 6
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$97 Roundtrip, found 6 hours ago
$97
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Mon, Mar 30 from Orlando Intl. to Washington Dulles Intl., returning Mon, Apr 6, priced at $97 found 6 hours ago
Wed, Apr 15 - Fri, Apr 17
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$104 Roundtrip, found 4 days ago
$104
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Apr 15 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Fri, Apr 17, priced at $104 found 4 days ago
Tue, Apr 7 - Tue, Apr 7
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Apr 7, priced at $114 found 6 days ago
Wed, May 6 - Tue, May 12
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, May 6 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, May 12, priced at $117 found 4 days ago
Wed, May 6 - Tue, May 12
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 6 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, May 12, priced at $117 found 4 days ago
Fri, May 8 - Mon, May 11
DEN
Denver Intl.
DCA
Ronald Reagan Washington National
$118 Roundtrip, found 4 hours ago
$118
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, May 8 from Denver Intl. to Ronald Reagan Washington National, returning Mon, May 11, priced at $118 found 4 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, Spirit Airlines, Southwest Airlines, JetBlue Airways, American 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.
The Churchill Hotel near Embassy Row
4.0-star property

The Churchill Hotel near Embassy Row

Apr 1 - Apr 5

4 night stay

Atlanta (ATL) to Washington (DCA)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $561, price is now $389 per person
$389
per person
found 1 day ago
Beacon Hotel & Corporate Quarters
3.5-star property

Beacon Hotel & Corporate Quarters

Apr 10 - Apr 12

2 night stay

Atlanta (ATL) to Washington (DCA)

Delta • Coach

Washington (DCA) to Atlanta (ATL)

Frontier Airlines • Coach
Price was $568, price is now $407 per person
$407
per person
found 1 day ago
Briar Patch Bed & Breakfast Inn
3.0-star property

Briar Patch Bed & Breakfast Inn

Apr 2 - Apr 8

6 night stay

Indianapolis (IND) to Washington (IAD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,381, price is now $1,002 per person
$1,002
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Atlanta to Winchester
View all trips

Winchester first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Place Arlington/Courthouse Plaza
3.0-star property

Hyatt Place Arlington/Courthouse Plaza

9.2/10 Wonderful! (1,004 reviews)

Apr 7 - Apr 10

3 night stay

Atlanta (ATL) to Washington (DCA)

American Airlines • Roundtrip • FirstClass
Price was $1,097, price is now $887 per person
$887
per person
found 1 day ago
Clean, wonderful staff and best location

Reviewed on Dec 28, 2025

Hotel Washington
5.0-star property

Hotel Washington

9/10 Wonderful! (2,375 reviews)

Apr 7 - Apr 10

3 night stay

Atlanta (ATL) to Washington (DCA)

American Airlines • Roundtrip • FirstClass
Price was $1,288, price is now $1,013 per person
$1,013
per person
found 1 day ago
Staff was great. Rooms were meh. Stayed overnight for a Christmas party- girls night out. First room had no doors to the bath. Second room had a view of a wall (dark) and the furniture was odd. Coffee maker was broken and only one pod. The rooftop is still one of the best in the city. Lobby bar was nice, but I miss the old one in the front which was classic and cozy. It’s a historic building and too bad it got “over modernized). Still it’s nice for DC.

Reviewed on Dec 21, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center
3.5-star property

Embassy Suites by Hilton Washington D.C. – Convention Center

9.2/10 Wonderful! (2,031 reviews)

Apr 7 - Apr 10

3 night stay

Atlanta (ATL) to Washington (DCA)

American Airlines • Roundtrip • FirstClass
Price was $1,272, price is now $1,021 per person
$1,021
per person
found 1 day ago
Great location, friendly service, and fantastic breakfast.

Reviewed on Jan 6, 2026

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

Winchester

Orbitz uses cutting edge mobile technology to help get you the best deals on Winchester flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

Find Cheap Winchester Flights And Hotel Rooms Using Our Mobile App

Orbitz not only guarantees low prices for flights to Winchester, we also offer Mobile Steals on our Orbitz on the Go mobile app where you can find great mobile-only deals on hotel rooms in the area.

Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Winchester can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Winchester. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Winchester to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

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 $118. But it was travelers flying in from Orlando (MCO) 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.