$79 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 8/14. 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.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Winchester

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

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

Thu, Aug 7 - Mon, Aug 11
Delta Logo
1:55 pm - 3:04 pmLGA-ORH
1h 09mnonstop
Delta Logo
3:55 pm - 5:06 pmORH-LGA
1h 11mnonstop
$153Delta
Find Deal
Wed, Jul 30 - Wed, Aug 6
Delta Logo
1:55 pm - 3:04 pmLGA-ORH
1h 09mnonstop
Delta Logo
3:48 pm - 4:59 pmORH-LGA
1h 11mnonstop
$173Delta
Find Deal
Thu, Aug 28 - Tue, Sep 2
JetBlue Logo
9:45 am - 12:39 pmMCO-ORH
2h 54mnonstop
JetBlue Logo
1:34 pm - 4:40 pmORH-MCO
3h 06mnonstop
$183JetBlue
Find Deal
Thu, Aug 14 - Sun, Aug 17
JetBlue Logo
12:05 pm - 3:03 pmFLL-ORH
2h 58mnonstop
JetBlue Logo
3:59 pm - 7:21 pmORH-FLL
3h 22mnonstop
$193JetBlue
Find Deal
Fri, Jul 25 - Sun, Jul 27
Delta Logo
1:55 pm - 3:04 pmLGA-ORH
1h 09mnonstop
Delta Logo
3:48 pm - 4:59 pmORH-LGA
1h 11mnonstop
$193Delta
Find Deal
Fri, Aug 15 - Wed, Aug 20
American Airlines Logo
6:10 am - 2:55 pmMCO-ORH
8h 45m1 stop
American Airlines Logo
3:20 pm - 9:31 amORH-MCO
18h 11m1 stop
$202American Airlines
Find Deal
Fri, Aug 1 - Fri, Aug 8
American Airlines Logo
7:00 am - 3:04 pmTPA-ORH
8h 04m1 stop
American Airlines Logo
3:20 pm - 9:05 amORH-TPA
17h 45m1 stop
$202American Airlines
Find Deal
Fri, Aug 15 - Wed, Aug 20
American Airlines Logo
6:10 am - 2:55 pmMCO-ORH
8h 45m2 stops
American Airlines Logo
3:20 pm - 9:31 amORH-MCO
18h 11m1 stop
$212American Airlines
Find Deal
Thu, Aug 14 - Thu, Aug 21
JetBlue Logo
6:45 am - 3:03 pmRDU-ORH
8h 18m1 stop
JetBlue Logo
3:59 pm - 11:59 pmORH-RDU
8h 00m1 stop
$220JetBlue
Find Deal
Tue, Jul 29 - Wed, Aug 6
JetBlue Logo
9:45 am - 12:39 pmMCO-ORH
2h 54mnonstop
JetBlue Logo
1:34 pm - 4:40 pmORH-MCO
3h 06mnonstop
$233JetBlue
Find Deal
Useful Info

Good to know - Book Cheap Winchester Plane Tickets

Low seasonFebruary
High seasonAugust
Cheapest flight$79
Best time to beat the crowds but there is an average 5% increase in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from New York LaGuardia Airport to Worcester

FAQs - booking Winchester flights

  • How long is the flight to Winchester?

    Flights from Fort Lauderdale3h 08m
    Flights from New York1h 10m
    Flights from Philadelphia1h 24m
    Flights from Orlando2h 59m
  • What is the cheapest flight to Worcester?

    In the last 3 days, the cheapest flight deal to Worcester was found on the route from New York, at $153 return. The most popular connection is from Orlando to Worcester and KAYAK users have found round-trip deals for as low as $183 in the last 3 days.

  • Which airlines fly to Worcester?

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

  • How to fly to Winchester?

    You cannot fly directly to Winchester. KAYAK recommends you fly to Worcester (ORH) (43.47 miles from Winchester). From there you can rent a car or get a taxi.

  • What airports are near Winchester?

    The closest airport is Worcester (ORH) (43.47 mi). Other nearby airports are Manchester (MHT) (49.06 mi), Lebanon Municipal (LEB) (59.12 mi) or Rutland (RUT) (59.25 mi). KAYAK recommends you fly to Worcester.

  • How far is Worcester Airport from central Worcester?

    Central Worcester is 4 miles away from Worcester Airport.

  • What is the name of Worcester’s airport?

    Worcester is served by Worcester Airport, also commonly referred to as Worcester. The airport code is ORH.

  • 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 Worcester Airport.
  • Looking for a cheap flight? 25% of our users found flights on this route for $104 or less one-way and $207 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winchester flight deals.

Reviews of the top 3 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
DeltaOverall score based on 7974 reviews
8.5Crew
7.9Comfort
7.9Entertainment
8.2Boarding
7.3Food
Airline reviews

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

2.0 Mediocrepuravi, Jul 2025STL - LGA
Read more Delta reviews

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

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.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

Above and beyond effort from this crew in a tough situation. So helpful and understanding. Thank you!

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

Everything you need to know for your flight to Winchester

Complete your trip to Winchester with a hotel stay or car rental

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.