Cheap flights To Winchester (DCA) from $25

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Cheap Flights to Winchester from $25 One Way, $54 Round Trip

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

Fri, Oct 24 - Sun, Oct 26
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$54 Roundtrip, just found
$54
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Oct 24 from Orlando Intl. to Washington Dulles Intl., returning Sun, Oct 26, priced at $54 just found
Thu, Sep 4 - Wed, Sep 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 4 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 10, priced at $68 just found
Sat, Sep 13 - Sat, Sep 13
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 2 days ago
$69
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Sep 13 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Sep 13, priced at $69 found 2 days ago
Thu, Sep 11 - Wed, Sep 17
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$89 Roundtrip, found 22 hours ago
$89
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Thu, Sep 11 from Los Angeles Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 17, priced at $89 found 22 hours ago
Thu, Sep 4 - Thu, Sep 4
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Sep 4 from Orlando Intl. to Ronald Reagan Washington National, returning Thu, Sep 4, priced at $124 found 1 day ago
Wed, Sep 3 - Tue, Sep 9
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$125 Roundtrip, found 4 days ago
$125
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Wed, Sep 3 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Sep 9, priced at $125 found 4 days ago
Wed, Oct 29 - Tue, Nov 4
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $137 found 4 hours ago
Wed, Oct 29 - Tue, Nov 4
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Oct 29 from Orlando Intl. to Washington Dulles Intl., returning Tue, Nov 4, priced at $137 found 4 hours ago
Wed, Oct 29 - Tue, Nov 4
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Oct 29 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $137 found 4 hours ago
Wed, Oct 29 - Tue, Nov 4
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$137 Roundtrip, found 4 hours ago
$137
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Wed, Oct 29 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Nov 4, priced at $137 found 4 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, JetBlue Airways, United, Southwest Airlines, American Airlines, Delta
Flight Price
$54
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.
DoubleTree by Hilton Hotel Laurel
4.0-star property

DoubleTree by Hilton Hotel Laurel

Oct 11 - Oct 18

7 night stay

Charlotte (CLT) to Baltimore (BWI)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $791, price is now $427 per person
$427
per person
found 1 day ago
Hotel Arboretum
2.0-star property

Hotel Arboretum

Oct 11 - Oct 18

7 night stay

Charlotte (CLT) to Washington (WAS)

Southwest Airlines • Roundtrip • Coach
Price was $896, price is now $432 per person
$432
per person
found 1 day ago
Kellogg Conference Hotel at Gallaudet University
3.0-star property

Kellogg Conference Hotel at Gallaudet University

Oct 13 - Oct 18

5 night stay

Charlotte (CLT) to Washington (WAS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,320, price is now $763 per person
$763
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.
YOTEL Washington DC
4.0-star property

YOTEL Washington DC

8.2/10 Very Good! (2,052 reviews)

Oct 14 - Oct 19

5 night stay

Orlando (MCO) to Washington (WAS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,237, price is now $820 per person
$820
per person
found 14 hours ago
Stayed here with my whole family , the hotel was clean and in good condition , friendly and accommodating staff , great location , 8min walking distance to Union Station ( lots of restaurants to eat) and 15 mins walk to National mall . The only thing is the hotel has weird policy like coffee done serving after 10 am ( coffee machine is at the hotels hallway each floor and can’t have it after that ) and swimming pool closes at 9pm . When you want to relax after your long day at the museum/ national mall - you can’t access the pool since it closes early . Hope they change their hours , except for those it’s really a nice place to stay at.

Reviewed on Jul 15, 2025

Pendry Washington DC - The Wharf
5.0-star property

Pendry Washington DC - The Wharf

9.2/10 Wonderful! (333 reviews)

Oct 14 - Oct 19

5 night stay

Orlando (MCO) to Washington (WAS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,318, price is now $2,159 per person
$2,159
per person
found 13 hours ago
Great spot on the Wharf near many restaurants and offices. Not far from downtown.

Reviewed on Jul 4, 2025

Hilton Washington DC Capitol Hill
4.0-star property

Hilton Washington DC Capitol Hill

9/10 Wonderful! (1,001 reviews)

Oct 14 - Oct 19

5 night stay

Orlando (MCO) to Washington (WAS)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,442, price is now $966 per person
$966
per person
found 14 hours ago
The staff was very courteous and helpful! The location is great!!

Reviewed on Jan 1, 2025

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Winchester

If you are looking for affordable flights to Winchester, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Winchester now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Winchester flights. With Orbitz, booking flights to Winchester is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Winchester flights by visiting the Orbitz site or mobile application.

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Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Winchester flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Winchester flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings 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 $54 to $137. But it was travelers flying in from Fort Lauderdale (FLL) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $25.
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.

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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.