$90 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 7/4. 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

Sat, Aug 16 - Tue, Aug 19
United Airlines Logo
12:40 pm - 2:16 pmIAD-DAY
1h 36mnonstop
United Airlines Logo
10:25 am - 12:02 pmDAY-IAD
1h 37mnonstop
$189United Airlines
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Sat, Jul 19 - Tue, Jul 22
American Airlines Logo
5:19 pm - 7:01 pmDCA-DAY
1h 42mnonstop
American Airlines Logo
7:25 pm - 8:59 pmDAY-DCA
1h 34mnonstop
$189American Airlines
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Sat, Aug 9 - Sat, Aug 16
American Airlines Logo
4:21 pm - 10:00 pmRDU-DAY
5h 39m1 stop
American Airlines Logo
6:38 am - 10:25 amDAY-RDU
3h 47m1 stop
$191American Airlines
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Sat, Jul 12 - Mon, Jul 14
United Airlines Logo
8:15 am - 9:51 amIAD-DAY
1h 36mnonstop
United Airlines Logo
7:48 pm - 9:25 pmDAY-IAD
1h 37mnonstop
$192United Airlines
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Tue, Aug 5 - Tue, Aug 12
American Airlines Logo
3:45 pm - 8:37 pmRDU-DAY
4h 52m1 stop
American Airlines Logo
6:07 am - 12:44 pmDAY-RDU
6h 37m1 stop
$192American Airlines
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Tue, Jul 8 - Tue, Jul 15
American Airlines Logo
10:09 pm - 11:43 pmDCA-DAY
1h 34mnonstop
American Airlines Logo
6:02 am - 7:38 amDAY-DCA
1h 36mnonstop
$194American Airlines
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Thu, Aug 7 - Tue, Aug 12
Delta Logo
1:40 pm - 8:16 pmDCA-DAY
6h 36m1 stop
Delta Logo
2:30 pm - 7:35 pmDAY-DCA
5h 05m1 stop
$209Delta
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Sat, Aug 9 - Sat, Aug 16
Delta Logo
11:07 am - 4:48 pmRDU-DAY
5h 41m1 stop
Delta Logo
4:30 pm - 8:37 pmDAY-RDU
4h 07m1 stop
$213Delta
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Thu, Jul 24 - Sun, Jul 27
Alaska Airlines Logo
6:30 pm - 8:37 pmLGA-DAY
2h 07mnonstop
Alaska Airlines Logo
9:27 am - 3:10 pmDAY-LGA
5h 43m1 stop
$471Alaska Airlines
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Sat, Jul 5 - Wed, Jul 9
Alaska Airlines Logo
6:00 am - 5:08 pmSEA-DAY
8h 08m1 stop
Alaska Airlines Logo
7:27 am - 3:17 pmDAY-SEA
10h 50m1 stop
$617Alaska Airlines
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Good to know - Book Cheap Winchester Plane Tickets

Low seasonFebruary
High seasonMay
Cheapest flight$90
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Washington Dulles Airport to Dayton

FAQs - booking Winchester flights

  • How long is the flight to Winchester?

    Flights from Chicago1h 26m
    Flights from Washington, D.C.1h 34m
    Flights from New York2h 02m
    Flights from Denver2h 59m
    Flights from Atlanta1h 40m
  • What is the cheapest flight to Dayton?

    In the last 3 days, the cheapest flight deal to Dayton was found on the route from Washington, D.C., at $189 return. The most popular connection is from Washington, D.C. to Dayton and KAYAK users have found round-trip deals for as low as $189 in the last 3 days.

  • Which airlines fly to Dayton?

    Many airlines fly to Dayton, the most common ones being American Airlines, United Airlines, and Delta. See the amount of flights per week for popular airlines flying to Dayton.

  • How to fly to Winchester?

    You cannot fly directly to Winchester. KAYAK recommends you fly to Dayton (DAY) (44.25 miles from Winchester). From there you can rent a car or get a taxi.

  • What airports are near Winchester?

    The closest airport is Dayton (DAY) (44.25 mi). Other nearby airports are Fort Wayne (FWA) (57.26 mi), Lima Allen County (AOH) (62.37 mi), Indianapolis (IND) (76.49 mi) or Cincinnati Cinci./N. Kentucky (CVG) (79.57 mi). KAYAK recommends you fly to Dayton.

  • How far is Dayton Airport from central Dayton?

    There are 10 miles between Dayton city center and Dayton Airport.

  • What is the name of Dayton’s airport?

    There is only 1 airport in Dayton, called Dayton Airport (DAY). It can also be referred to as Dayton, Dayton Intl, or James M Cox Dayton Intl.

  • 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 Dayton Airport.
  • Looking for cheap airfare to Winchester? 25% of our users found round-trip tickets to Winchester for the following prices or less: From Denver $359
  • 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

Same crew flew with us from Palm Springs to Bellingham, so they were great! Friendly and kind from start to finish. Great experience!

10.0 ExcellentMichelle, Jun 2025SEA - BLI
Read more Alaska Airlines reviews

Same crew flew with us from Palm Springs to Bellingham, so they were great! Friendly and kind from start to finish. Great experience!

Eddie, our flight attendant in the back was excellent. He was very kind and concerned for our happiness and comfort before and during our flight. He made the experience great. We had to deplane due to a ground delay and he made sure we had snacks and water to keep us comfortable while we waited. Overall, it was a great experience!

One of the stewardess, Tre, went above and beyond to ensure my comfort!

Alaska app and website had numerous problems so couldn’t get boarding passes or check seats

Flight was very warm. It felt like there was no working AC.

I liked the food. The WiFi was out and the flight was late.

Flight was delayed which caused us to have to change our connecting flight. Grilled cheese sandwich was served very hot.

Big delay of over 7 hours on next leg of trip with Alaska. Would have been nice to have food or something

Very good. Gate personnel were excellent flight attendants were also able to change my seat at the last minute everyone, courteous, polite, and.

I was so cold. I am so glad I brought a short sleeve shirt and a long sleeve shirt and a jacket. Also knee high socks and slippers

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Boarding was organised and relaxed. Crew were fantastic! Seats were lacking padding causing butt pain and stiffness.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

Gate agent did not hold flight for connection, provided no assistance to get new flight

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

United airlines, mediocre at best. No issues , nothing great . Worked for me

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

Tight! Seats are not designed for those of us who wear extra-large clothes.

The non-stop flight from Grand Rapids was excellent. I neither expected or needed a budget flight and Allegiant made the trip easy and for an affordable price, Arriving at the Mesa Airport (AZA) is a delight compared to the international airport. For our return flight, we were able to arrive 75 minutes before the flight, return the rental car, check our bag and make it to the gate in plenty of time. That would never happen at most airports.

Easiest flights I’ve ever taken. Plane was comfortable without overly crowded seating.

Terrible. Still have not received the refund from them. They sent it to some account that I don't even know. Spoke with costumer service and they are unable to help.

I didn’t like it at all. I miss my second flight because of the delay on Allegiant Air now I m stuck in MCO.

Good, but a bit late on take off after loading. Don't like charging for carry ons!

First time flying with them and will definitely fly again in the future. Crew was so nice and friendly, fought was seamless. They are simple planes, no entertainment, but it’s fine for a short flight or if you have personal devices Rates are competitive, and they did so well with keeping the flight on time after a tropical storm, where other airlines had delays and cancellations.

They boarded passengers that sat in the back of the plane first, making boarding very efficient.

I didn't even take this flight. My plans changed and I couldn't get ahold of customer service and the website kept breaking down during the attempt to change the flight. I wound up taking another airline entirely and eating the cost.

The worst flying experience ever 3 delays. No accommodations. Had to deboard the plane after being delayed.

Pretty bad gate mgmt upon arrival. No open gates and we had to wait at midnight. Shouldn’t be a surprise that an aircraft is coming in.

We started with trouble checking in 24 hours early. Then my husband did not get his TSA precheck. Finally flight delayed due to no crew. I know things happen

Boarding was very efficient. Everyone got on board and we got on our way very quickly. It was frustrating that the entertainment app was not functioning properly. I was not able to activate some of the movies offered. The crew on this flight appears to be pretty grumpy. They had no smile on their faces. I felt like they were doing us a favor for being there.

Mechanical delay and no compensation. Missed connection as a result of their delay. Mediocre performance and service. Horrible airline currently with horrible culture.

Comfortable plane ride however on delays disappointment no real details as to why the delays when other flights are leaving the airport

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

They changed our Gate 5 times, and concourse twice. Changed our seats twice.

Delayed because of weather in Nashville. I think God or some higher power generally has cursed me when it comes to flying out of Charlotte on American. I'm delayed pretty much everytime. We need Team Cobra Kai types to come in and "sweep the leg(s)" of the Charlotte ops people on principle. Don't let the sweet southern rocking chairs fool you, Charlotte is a sinkhole

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

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