Cheap flights To Winchester (DCA) from $30

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Cheap Flights to Winchester from $30 One Way, $66 Round Trip

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

Thu, Aug 27 - Mon, Aug 31
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Orlando Intl. to Washington Dulles Intl., returning Mon, Aug 31, priced at $66 found 2 days ago
Thu, Sep 10 - Wed, Sep 16
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Sep 16, priced at $66 found 2 days ago
Mon, Aug 24 - Fri, Aug 28
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
Select Breeze Airways flight, departing Mon, Aug 24 from Orlando Intl. to Washington Dulles Intl., returning Fri, Aug 28, priced at $90 just found
Fri, Sep 11 - Mon, Sep 14
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$109 Roundtrip, found 3 days ago
$109
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Sep 11 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Sep 14, priced at $109 found 3 days ago
Tue, Oct 6 - Tue, Oct 13
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 2 hours ago
$117
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Logan Intl. to Ronald Reagan Washington National, returning Tue, Oct 13, priced at $117 found 2 hours ago
Thu, Sep 24 - Sat, Sep 26
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Sep 24 from Logan Intl. to Washington Dulles Intl., returning Sat, Sep 26, priced at $117 found 3 hours ago
Thu, Oct 8 - Mon, Oct 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$117 Roundtrip, found 3 hours ago
$117
Roundtrip
found 3 hours ago
Select Delta flight, departing Thu, Oct 8 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Oct 12, priced at $117 found 3 hours ago
Tue, Aug 4 - Tue, Aug 4
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Aug 4, priced at $157 found 5 days ago
Tue, Oct 6 - Wed, Oct 14
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Los Angeles Intl. to Ronald Reagan Washington National, returning Wed, Oct 14, priced at $168 found 3 days ago
Tue, Nov 10 - Sun, Nov 15
SEA
Seattle - Tacoma Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Tue, Nov 10 from Seattle - Tacoma Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Nov 15, priced at $197 found 2 hours ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, Breeze Airways, Southwest Airlines, Delta, JetBlue Airways, United
Flight Price
$66
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

Aug 30 - Sep 4

5 night stay

Cincinnati (CVG) to Baltimore (BWI)

American Airlines • Coach

Baltimore (BWI) to Cincinnati (CVG)

Frontier Airlines • Coach
Price was $794, price is now $532 per person
$532
per person
found 8 hours ago
InterContinental Washington D.C. - The Wharf by IHG
5.0-star property

InterContinental Washington D.C. - The Wharf by IHG

Aug 30 - Sep 4

5 night stay

Cincinnati (CVG) to Baltimore (BWI)

American Airlines • Coach

Baltimore (BWI) to Cincinnati (CVG)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,253, price is now $793 per person
$793
per person
found 8 hours ago
Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

Aug 30 - Sep 4

5 night stay

Cincinnati (CVG) to Baltimore (BWI)

American Airlines • Coach

Baltimore (BWI) to Cincinnati (CVG)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,025, price is now $688 per person
$688
per person
found 8 hours ago
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Winchester premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Hive
3.5-star property

Hotel Hive

9.2/10 Wonderful! (1,514 reviews)

Sep 3 - Sep 8

5 night stay

Dallas (DFW) to Baltimore (BWI)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $825, price is now $533 per person
$533
per person
just found
Perfect boutique hotel for business travel. This property made me want to stay for an extra day! From the rooftop bar to the brick-lined lobby space, it was perfect for my travel needs. Yes, extra clean. Affordable. Small, intimate rooms. And La Colombe Coffee! Like I said, ideal for quick business travel. (Will stay again.)

Reviewed on Jul 12, 2026

Club Quarters Hotel in Washington DC
3.0-star property

Club Quarters Hotel in Washington DC

8.8/10 Excellent! (1,902 reviews)

Sep 3 - Sep 8

5 night stay

Dallas (DFW) to Baltimore (BWI)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,050, price is now $675 per person
$675
per person
just found
Yes

Reviewed on Jul 13, 2026

InterContinental Washington D.C. - The Wharf by IHG
5.0-star property

InterContinental Washington D.C. - The Wharf by IHG

9.4/10 Exceptional! (1,196 reviews)

Sep 3 - Sep 8

5 night stay

Dallas (DFW) to Baltimore (BWI)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,173, price is now $762 per person
$762
per person
just found
This hotel is located in very safe neighborhood and a close proximity to every tourist attractions. Highly recommend it to family or solo guest visiting the DC area.

Reviewed on Jul 14, 2026

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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 $66 to $197. But it was travelers flying in from Orlando (MCO) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $30.
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.