Cheap flights To Winchester (DCA) from $29

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Cheap Flights to Winchester from $29 One Way, $85 Round Trip

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

Fri, Mar 27 - Sat, Apr 4
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 4 days ago
$85
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Mar 27 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Apr 4, priced at $85 found 4 days ago
Thu, Apr 30 - Fri, May 8
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$91 Roundtrip, found 2 hours ago
$91
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Washington Dulles Intl., returning Fri, May 8, priced at $91 found 2 hours ago
Sat, Apr 25 - Tue, Apr 28
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$97 Roundtrip, just found
$97
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Apr 25 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Apr 28, priced at $97 just found
Fri, May 1 - Fri, May 8
MCO
Orlando Intl.
IAD
Washington Dulles Intl.
$112 Roundtrip, found 2 days ago
$112
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, May 1 from Orlando Intl. to Washington Dulles Intl., returning Fri, May 8, priced at $112 found 2 days ago
Fri, Apr 17 - Sun, Apr 19
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$144 Roundtrip, just found
$144
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Apr 17 from Orlando Intl. to Ronald Reagan Washington National, returning Sun, Apr 19, priced at $144 just found
Fri, May 15 - Mon, May 18
BOS
Logan Intl.
IAD
Washington Dulles Intl.
$144 Roundtrip, found 11 hours ago
$144
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Fri, May 15 from Logan Intl. to Washington Dulles Intl., returning Mon, May 18, priced at $144 found 11 hours ago
Tue, May 5 - Wed, May 6
LAX
Los Angeles Intl.
DCA
Ronald Reagan Washington National
$150 Roundtrip, found 1 hour ago
$150
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, May 5 from Los Angeles Intl. to Ronald Reagan Washington National, returning Wed, May 6, priced at $150 found 1 hour ago
Fri, May 1 - Tue, May 5
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, May 1 from Logan Intl. to Ronald Reagan Washington National, returning Tue, May 5, priced at $154 found 2 days ago
Sat, Apr 11 - Thu, Apr 16
MSP
Minneapolis - St. Paul Intl.
IAD
Washington Dulles Intl.
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Apr 11 from Minneapolis - St. Paul Intl. to Washington Dulles Intl., returning Thu, Apr 16, priced at $158 found 1 day ago
Mon, Apr 27 - Sat, May 2
MSP
Minneapolis - St. Paul Intl.
DCA
Ronald Reagan Washington National
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Apr 27 from Minneapolis - St. Paul Intl. to Ronald Reagan Washington National, returning Sat, May 2, priced at $160 found 2 days ago

Winchester Flight Information

Traveling To
Winchester
Destination Airport IATA Code
DCA
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Breeze Airways, Southwest Airlines, JetBlue Airways
Flight Price
$85
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.
Hyatt Place Arlington/Courthouse Plaza
3.0-star property

Hyatt Place Arlington/Courthouse Plaza

May 13 - May 17

4 night stay

Boston (BOS) to Washington (DCA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,237, price is now $868 per person
$868
per person
found 1 day ago
The Dupont Circle Hotel
4.5-star property

The Dupont Circle Hotel

Apr 29 - May 4

5 night stay

Boston (BOS) to Washington (DCA)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,252, price is now $887 per person
$887
per person
found 1 day ago
Eurostars Saint Gregory Dupont Circle Georgetown
4.0-star property

Eurostars Saint Gregory Dupont Circle Georgetown

May 13 - May 17

4 night stay

Boston (BOS) to Washington (DCA)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,694, price is now $1,228 per person
$1,228
per person
found 1 day ago
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See all available trips from Boston to Winchester
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Winchester first class flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Hotel Baltimore - BWI Airport
4.0-star property

DoubleTree Hotel Baltimore - BWI Airport

8.4/10 Very Good! (1,248 reviews)

May 8 - May 10

2 night stay

Boston (BOS) to Baltimore (BWI)

Delta • Roundtrip • FirstClass
Price was $647, price is now $592 per person
$592
per person
found 12 hours ago
always clean, dining room offers some nice choices.

Reviewed on Jan 30, 2026

Hyatt Place Baltimore Inner Harbor
3.5-star property

Hyatt Place Baltimore Inner Harbor

8.4/10 Very Good! (2,459 reviews)

May 8 - May 10

2 night stay

Boston (BOS) to Baltimore (BWI)

Delta • Roundtrip • FirstClass
Price was $714, price is now $654 per person
$654
per person
found 12 hours ago
We had a good time there! The room was really clean and spaced out but we had hard time sleeping due to the heat being too loud at night and noisy neighbors but overall had a good time! It was nice to have valet parking but I wish the breakfast was a bit flavorful and slightly more hot!

Reviewed on Feb 1, 2026

The Inn at Henderson's Wharf, an Ascend Collection Hotel
3.0-star property

The Inn at Henderson's Wharf, an Ascend Collection Hotel

9.2/10 Wonderful! (770 reviews)

May 8 - May 10

2 night stay

Boston (BOS) to Baltimore (BWI)

Delta • Roundtrip • FirstClass
Price was $783, price is now $738 per person
$738
per person
found 12 hours ago
Everything was fantastic! A perfect holiday treat.

Reviewed on Dec 25, 2025

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Winchester

Save more on flights to Winchester while making top-quality travel arrangements. At Orbitz we provide access to low cost flights, hotel lodgings and other discounts, along with superior customer service and an unbeatable satisfaction guarantee.

Compare And Book Discount Flights to Winchester

Now it is easier than ever to find a discount Winchester flight. Orbitz users can compare airfares for both international and domestic flights and can quickly determine the best hotels and car rental companies to use. You may also check out hotel and other reviews along with a number of travel tips, making your visit to an unfamiliar destination enjoyable and hassle-free.

Use Your Mobile Phone To Secure A Low Cost Flight To Winchester

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Boost Your Frequent Flyer Rewards

You even retain your ability to earn frequent flier points and rewards when purchasing your tickets with Orbitz for Winchester flights. Enter your frequent flyer information into your Orbitz profile to start earning rewards.

You will find that Orbitz is a very low cost, yet very effective travel planner. Free updates via your mobile phone device will help to keep you and all relevant parties informed of important flight updates. With access to unbeatable sales on all travel essentials, Orbitz makes booking an affordable flight to Winchester a breeze.

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 $85 to $160. But it was travelers flying in from Orlando (MCO) who snapped up the biggest bargains. One-way flights to Winchester fell to a low $29.
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.