Cheap flights To Winchester (DCA) from $32

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Cheap Flights to Winchester from $32 One Way, $64 Round Trip

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

Thu, Jul 31 - Sat, Aug 9
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$64 Roundtrip, found 6 days ago
$64
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Thu, Jul 31 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Aug 9, priced at $64 found 6 days ago
Mon, Nov 3 - Wed, Nov 5
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Nov 3 from Orlando Intl. to Ronald Reagan Washington National, returning Wed, Nov 5, priced at $85 found 1 day ago
Mon, Sep 22 - Mon, Sep 22
FLL
Fort Lauderdale - Hollywood Intl.
DCA
Ronald Reagan Washington National
$86 Roundtrip, found 10 hours ago
$86
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Mon, Sep 22 from Fort Lauderdale - Hollywood Intl. to Ronald Reagan Washington National, returning Mon, Sep 22, priced at $86 found 10 hours ago
Sat, Aug 23 - Sat, Aug 23
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$86 Roundtrip, found 19 hours ago
$86
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Sat, Aug 23 from Orlando Intl. to Ronald Reagan Washington National, returning Sat, Aug 23, priced at $86 found 19 hours ago
Fri, Jul 25 - Sun, Jul 27
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jul 25 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jul 27, priced at $87 just found
Thu, Nov 13 - Mon, Nov 17
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$88 Roundtrip, found 5 days ago
$88
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Nov 13 from Orlando Intl. to Washington Dulles Intl., returning Mon, Nov 17, priced at $88 found 5 days ago
Mon, Sep 29 - Thu, Oct 2
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$89 Roundtrip, found 23 hours ago
$89
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Mon, Sep 29 from Orlando Intl. to Ronald Reagan Washington National, returning Thu, Oct 2, priced at $89 found 23 hours ago
Tue, Sep 23 - Tue, Oct 21
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$91 Roundtrip, found 16 hours ago
$91
Roundtrip
found 16 hours ago
Select United flight, departing Tue, Sep 23 from Orlando Intl. to Washington Dulles Intl., returning Tue, Oct 21, priced at $91 found 16 hours ago
Fri, Oct 17 - Mon, Oct 20
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$91 Roundtrip, found 13 hours ago
$91
Roundtrip
found 13 hours ago
Select Delta flight, departing Fri, Oct 17 from Orlando Intl. to Ronald Reagan Washington National, returning Mon, Oct 20, priced at $91 found 13 hours ago
Sat, Aug 23 - Tue, Aug 26
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 23 from Orlando Intl. to Ronald Reagan Washington National, returning Tue, Aug 26, priced at $91 found 1 day ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Spirit Airlines, Southwest Airlines, JetBlue Airways, United, Delta, American Airlines, Frontier Airlines
Flight Price
$64
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.
Element Arundel Mills BWI Airport
3.0-star property

Element Arundel Mills BWI Airport

Aug 9 - Aug 16

7 night stay

Boston (BOS) to Baltimore (BWI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
DoubleTree Hotel Baltimore - BWI Airport
4.0-star property

DoubleTree Hotel Baltimore - BWI Airport

Aug 9 - Aug 16

7 night stay

Boston (BOS) to Baltimore (BWI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Pier 5 Hotel Baltimore
3.5-star property

Pier 5 Hotel Baltimore

Aug 9 - Aug 16

7 night stay

Boston (BOS) to Baltimore (BWI)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
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Winchester first class flight packages

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

Riggs Washington DC

9.4/10 Exceptional! (1,446 reviews)

Aug 12 - Aug 15

3 night stay

Boston (BOS) to Washington (DCA)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Rooms poorly lit. No drawers. Odd and inconvenient shower attachments. Great Riggs bar and coffee room. Staff very friendly and helpful.

Reviewed on Nov 23, 2024

Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

9/10 Wonderful! (1,006 reviews)

Aug 12 - Aug 15

3 night stay

Boston (BOS) to Washington (DCA)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Always love staying at this property when I'm in DC. It's convenient location to other points around the city, easy access via car or rail from the airport, super-friendly staff and comfy, clean rooms are a bonus.

Reviewed on Mar 28, 2025

Hotel Washington
5.0-star property

Hotel Washington

9/10 Wonderful! (2,257 reviews)

Aug 12 - Aug 15

3 night stay

Boston (BOS) to Washington (DCA)

Delta • Roundtrip • FirstClass
per person
found 1 day ago
Central location to major monuments.

Reviewed on Jul 6, 2025

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See all available trips from Boston to Winchester
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Winchester

End your search for discount fares on flights to Winchester. Orbitz has all the best prices on Winchester flights. With Orbitz, you can expect:

Cheap Deals on Flights to Winchester

We offer big discounts and last-minute savings on Winchester flights. We make it easy for you to research, plan, and book your flight to Winchester — all while offering great low fares. With guaranteed low prices and cutting-edge mobile tools, the perfect trip begins on Orbitz.

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Get alerts, updates, or book your Winchester flight or other flights wherever you are. Download our free apps for iPhone, Android, and iPad or visit our mobile site at m.orbitz.com to conveniently review or change your air travel plans. We can also send free alerts about your Winchester flight to your email or mobile phone, so you get advance warning about potential disruptions and flight delays. Need to book a hotel with your Winchester flight? Access exclusive, mobile-only deals via our mobile site and free apps – even on the same day.

Great Customer Care

We want to make your travel booking experience smooth and easy, from planning and researching Winchester flights to the actual booking. If you want to cancel your flight to Winchester, many tickets can be conveniently cancelled online. Contact our Customer Service to make changes to your air ticket.

Miles or Points Toward Frequent Flyer Programs

Much like booking with an airline directly, you can earn frequent flyer miles or points on qualified flights to Winchester with Orbitz. When completing your booking, just fill in your frequent flyer number for the airline you are flying with or for one of its available partner airlines.

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 $64 to $91. But it was travelers flying in from Boston (BOS) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $32.
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.