$30 Find Cheap Flights to Winchester

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Winchester departing on 10/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights to Winchester

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Winchester that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals to Winchester

Fri, Oct 24 - Mon, Oct 27
Frontier Logo
10:20 pm - 12:06 amATL-IAD
1h 46mnonstop
Frontier Logo
6:00 am - 7:58 amIAD-ATL
1h 58mnonstop
$48Frontier
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Fri, Oct 24 - Sun, Oct 26
Frontier Logo
6:24 pm - 8:38 pmTPA-IAD
2h 14mnonstop
Frontier Logo
9:33 pm - 11:56 pmIAD-TPA
2h 23mnonstop
$58Frontier
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Tue, Sep 23 - Tue, Sep 23
United Airlines Logo
12:10 pm - 4:12 pmDFW-IAD
3h 02mnonstop
United Airlines Logo
5:20 pm - 7:36 pmIAD-DFW
3h 16mnonstop
$134United Airlines
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Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
12:38 pm - 4:47 pmDFW-IAD
3h 09mnonstop
American Airlines Logo
11:47 am - 2:00 pmIAD-DFW
3h 13mnonstop
$139American Airlines
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Wed, Sep 3 - Wed, Sep 10
American Airlines Logo
6:49 pm - 10:48 pmDFW-IAD
2h 59mnonstop
American Airlines Logo
11:47 am - 2:00 pmIAD-DFW
3h 13mnonstop
$142American Airlines
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Sat, Aug 30 - Wed, Sep 3
United Airlines Logo
5:30 am - 7:10 amBOS-IAD
1h 40mnonstop
United Airlines Logo
3:55 pm - 5:34 pmIAD-BOS
1h 39mnonstop
$144United Airlines
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Sat, Aug 30 - Sat, Sep 6
Delta Logo
7:15 am - 11:26 pmORD-IAD
15h 11m1 stop
Delta Logo
5:25 pm - 9:35 pmIAD-ORD
5h 10m1 stop
$227Delta
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Tue, Aug 26 - Tue, Sep 2
Delta Logo
11:05 am - 5:34 pmORD-IAD
5h 29m1 stop
Delta Logo
6:00 am - 10:20 amIAD-ORD
5h 20m1 stop
$237Delta
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Sat, Sep 13 - Sat, Sep 20
Alaska Airlines Logo
4:20 pm - 12:23 amSEA-IAD
5h 03mnonstop
Alaska Airlines Logo
7:00 am - 9:38 amIAD-SEA
5h 38mnonstop
$251Alaska Airlines
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Sat, Sep 13 - Sat, Sep 20
Alaska Airlines Logo
11:30 pm - 7:33 amSEA-IAD
5h 03mnonstop
Alaska Airlines Logo
6:09 pm - 8:56 pmIAD-SEA
5h 47mnonstop
$252Alaska Airlines
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Good to know - Book Cheap Winchester Plane Tickets

Low seasonFebruary
Cheapest flight$30
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Tampa to Washington Dulles Airport

Flights to Winchester: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew to Winchester 
SuzetteFlew with Alaska AirlinesSEA-IADMay 2025
Take a shower before arriving at airport and don't wear perfume at all! Pack bags tight, so boarding is smooth and quick.
DanielFlew with Alaska AirlinesSEA-IADMay 2025
Seatac has gnarly traffic right now, took 35min to get from highway exit to the terminal
Verified travelerFlew with United AirlinesBDL-IADDec 2024
small overheads on small planes, sometimes delayed, don't make tight connection at Dulles
JasonFlew with United AirlinesDEN-IADNov 2024
DIA is a large airport. Get there early.
Verified travelerFlew with United AirlinesRIC-IADJul 2024
Know where your connecting gate. You can use the airline app to bring up a map and it can give you directions and time from landing gate to departure gate.
karenFlew with Alaska AirlinesLAX-IADJun 2024
Personal tips are bring your own food if you're hungry; keep foot space as open as possible for leg room; pack your patience
Verified travelerFlew with Alaska AirlinesLAX-IADJun 2024
Get to the airport on time because traffic in LA is unexpected
BindulFlew with United AirlinesDEN-IADFeb 2024
There are multiple flights between DEN and IAD everyday, including some wide bodies. Try and get on one of the wide bodies whenever possible.
PatriciaFlew with United AirlinesPBI-IADJan 2024
Take DCA instead of IAD to avoid those stupid overpacked people movers

FAQs - booking Winchester flights

  • How long is the flight to Winchester?

    Flights from Dallas3h 09m
    Flights from Tampa2h 30m
    Flights from Orlando2h 25m
    Flights from Atlanta1h 58m
    Flights from Los Angeles5h 15m
  • What is the cheapest flight to Washington Dulles Airport?

    In the last 3 days, the cheapest flight deal to Washington Dulles Airport was found on the route from Tampa, at $48 return. The most popular connection is from Atlanta to Washington Dulles Airport and KAYAK users have found round-trip deals for as low as $48 in the last 3 days.

  • Which airlines fly to Washington Dulles Airport?

    Many airlines fly to Washington Dulles Airport, the most common ones being United Airlines, Delta, and Southern / Mokulele. See the amount of flights per week for popular airlines flying to Washington Dulles Airport.

  • How to fly to Winchester?

    You cannot fly directly to Winchester. KAYAK recommends you fly to Washington, D.C. Dulles Intl (IAD) (41.63 miles from Winchester). From there you can rent a car or get a taxi.

  • What airports are near Winchester?

    The closest airport is Washington, D.C. Dulles Intl (IAD) (41.64 mi). Other nearby airports are Frederick (FDK) (45.1 mi), Washington, D.C. All airports (WAS) (63.67 mi) or Washington, D.C. Reagan-National (DCA) (64.64 mi). KAYAK recommends you fly to Washington, D.C. Dulles Intl.

  • How far is Washington, D.C. Dulles Intl Airport from central Washington, D.C.?

    Washington, D.C. Dulles Intl Airport is 22 miles from the center of Washington, D.C..

  • How does KAYAK find such low prices on flights to Winchester?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Winchester.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Winchester?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Winchester is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Winchester?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Winchester with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Winchester?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Winchester up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Winchester

  • There is no major airport in Winchester. It is instead served by Washington, D.C. Dulles Intl Airport.
  • Looking for cheap airfare to Winchester? 25% of our users found round-trip tickets to Winchester for the following prices or less: From Los Angeles $1,026, from Boston $1,031, from Miami $1,066
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winchester flight deals.

Reviews of the top 5 airlines flying to Winchester

 
Need help choosing which airline to fly with from the United States to Winchester? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Alaska AirlinesOverall score based on 10000 reviews
8.1Boarding
7.1Food
7.1Entertainment
7.8Comfort
8.5Crew
Airline reviews

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

8.0 ExcellentAnonymous, Jul 2025ORD - PDX
Read more Alaska Airlines reviews

Checking in very confusing compared to Hawaiian Airlines - much simpler! Front checking in at airport can improve. Hawaiian service always gives the extra mile, with a smile. Alaska can use and spread the Aloha Spirit. Mahalo nui loa Thank you 🤙

I was in the middle seat in the last row but that wasn’t their fault. It is why I rated the flight as mediocre, also the landing was a little rough. The good was really good. The self service luggage belt at SEATAC stopped working right when I reached it. I was literally placing my bag on the small belt when the main belt stopped. I understand that it wasn’t just Alaska but the entire side of the terminal. It took the agents about 20 minutes to arrive at a game plan and it certainly wasn’t flawless but they arranged for our luggage to be taken to the plane the old fashioned way by hand. Understandably, the plane was late in leaving. The flight took the proper amount of time and instead of arriving at OAK at 1:45, we got there at 2:30. I took my time getting to baggage claim because I knew it would be late if it was there at all. Sure enough it wasn’t but there was an agent there to greet me and inform me about my luggage. Long story longer, they delivered my luggage to where I was staying which was an hour away from the airport. Alaska has instituted a delivery type tracking system through my email that kept me informed of where my luggage was the whole time. WELL DONE!!

The flight was very smooth. The crew was very friendly.

Very nice as always. Not that it’s anyone’s fault really but for some reason the seat (16C) was really hard…. Not typical for your planes… dunno what or why… maybe it was just me ?, The flight was great otherwise

Flight attendant was rude when I advised her that the bathroom had no paper towels or tissue paper.

Crew was very friendly. Our bags showed up at the carousel within 20 minutes of arrival.

Flight was delayed and hour due to tire issue. First flight of the day, this issue should have been discovered prior to boarding.

Both legs of the trip were delayed about an hour. Planes were new, liked the WiFi availability and entertainment available. Crew was very good. People were happy and helpful. Liked the pilots - they provided updates throughout the flights. Snacks were underwhelming. Drinks were good! Like the smaller sodas and they actually came through the cabin 2x which was great. In Seattle airport the construction caused much confusion for Alaska. Process of printing own tags, etc was chaotic for people who didn’t check in online prior to arrival which in turn caused issues for those who did. Plus airport gates were too small for the number of people flying.

Plane was delayed getting boarded and then again delayed in take-off order. Alaska Airlines must have very little clout at JFK so they don't get priority treatment. All the delays meant we missed the last flight from Portland to Eugene. Alaska did give us hotel voucher for the night...but sent us to a downtown Portland hotel rather than to a nearby airport motel which made for a longer ride at night and then again in the morning. Just made an already long, late night even longer. Hotel was an old outdated Hilton in a slightly seedy part of town. Alaska gave us Lyft vouchers for getting to the hotel, but the return voucher for getting back to the airport in the morning didn't work.

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Food was surprisingly good but the WiFi was not great

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

Severe turbulence. Captain never came on to reassure passengers after things settled down.

My first flight was delayed 5 hours. The 2nd flight was canceled til the next day and the never even tried to compensate for it. Worse I was delayed again on the flight the rebooked me on.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

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