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$69 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 8/27. 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
0 bags
Fri 7/12
Fri 7/19

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Low season

February

High season

July

Cheapest flight

$69
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from New York John F Kennedy Airport to Worcester

FAQs - booking Winchester flights

  • How long is the flight to Winchester?

    Flights from Fort Lauderdale3h 09m
    Flights from New York1h 11m
    Flights from Orlando3h 02m
  • What is the cheapest flight to Worcester?

    Based on KAYAK searches from the last 72 hours, if you fly from New York, you should have a good chance of getting the best deal to Worcester as it was the cheapest place to fly from. Prices were found for as low as $69 one-way and $133 for a round-trip flight. Also in the last 72 hours, the most popular connection to Worcester was from Orlando and the lowest price for a round-trip flight was $162.

  • Which airlines fly to Worcester?

    JetBlue, American Airlines and Delta are the most frequent flyers to Worcester from United States. 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 from central Worcester?

    Central Worcester is 4 miles away from Worcester.

  • What is the name of Worcester’s airport?

    Worcester is served by Worcester, 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.

See more FAQs

Top tips for finding cheap flights to Winchester

  • There is no major airport in Winchester. It is instead served by Worcester Airport.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winchester flight deals.

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 10000 reviews
7.9Comfort
7.4Food
8.0Entertainment
8.2Boarding
8.6Crew
Airline reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

2.0 MediocreCraig, Jun 2024CVG - LGA
Read more about Delta reviews

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Paid for premium economy had no tv the whole time the crew tried to reset/reboot but would not work they said they would put a trouble ticket in for it. We had 3 seats my tv was the only one that didn't work. They cancelled our flight re worked us on another that left us at airport over night on the floor I have a ten year old and a 78 diabetic mother which also had shingles and suffers from nerve pain in legs and back. Requested wheelchair service at all airports after the re route NO wheelchair service was there to help. WORST experience we have ever had. Went to American airlines assistance it was closed. I AM FURIOUS!!! I expect some sort of compensation from this traumatic experience and no need for flying points we don't plan on using American airlines again!!!!

This is by far the worst experience I have had with American Airlines. The start of this trip was a complete disaster. I purposely planned my trip so that I would weather any delays so that I could make very important meeting at the Pentagon. My flight was cancelled because of maintenance and I was put on the first flight the next day but I was late to the meeting. After a long week at the Pentagon I just wanted to go home and my flight home which was early in the day was delayed. Eventually the flight was delayed until the next day. I was not authorized a hotel room because DCA was my point of origin. So I paid for a hotel out of pocket. The flight this morning was boarded then deplaned because the aircraft was hot. The flow of information was not happening in DCA and made it worse when the news was bad. I am going to take a break from American for my next few military flights. Hopefully whatever has been going on with American Airlines will be resolved.

We had a 2 hour delay. The seats were smaller than most other airlines. The person in front of us wanted to lay back and we had to stop her because she was pressing against my girlfriend’s legs. We had to ask her to sit up and not lay back due to the lack of room.

Everything was fine once we actually got on our flight. It was more then annoying they canceled (delayed) our flight. We lost out on a day of our trip along with money on our stay. Plus we had to book another hotel. So expensive.

This flight was canceled and delayed several times without explanation. The plane was freezing cold and no wifi for messaging. Getting off the plane was terribly unorganized and felt like it took forever….

The flight was delayed several times without explanation. The seats were terribly uncomfortable and wifi isn’t included. All these make for a less than ideal flight.

The flights was delayed by hours and it was the firmest landing I have experienced in my life. My back is still sore.

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Terrible. I didn’t fly and I had an important meeting the next day.

Equipment swap led to 2+ hour delay on international flight. And to top it off, boarding took forever.

Book Cheap Winchester Plane Tickets

Recent round-trip flight deals

6/23Sun
nonstopAmerican Airlines
1h 07mJFK-ORH
6/30Sun
nonstopAmerican Airlines
1h 18mORH-JFK
$133
7/13Sat
nonstopJetBlue
3h 04mFLL-ORH
7/16Tue
nonstopJetBlue
3h 12mORH-FLL
$142
6/22Sat
nonstopAmerican Airlines
1h 07mJFK-ORH
6/23Sun
nonstopAmerican Airlines
1h 18mORH-JFK
$153
8/29Thu
nonstopJetBlue
2h 55mMCO-ORH
9/2Mon
nonstopJetBlue
3h 09mORH-MCO
$162
7/13Sat
2 stopsAmerican Airlines
17h 40mFLL-ORH
7/16Tue
2 stopsAmerican Airlines
22h 35mORH-FLL
$176
7/11Thu
nonstopJetBlue
3h 04mFLL-ORH
7/18Thu
nonstopJetBlue
3h 12mORH-FLL
$183
7/31Wed
nonstopJetBlue
2h 55mMCO-ORH
8/23Fri
nonstopJetBlue
3h 09mORH-MCO
$188
7/30Tue
1 stopDelta
4h 57mMCO-ORH
8/23Fri
1 stopDelta
6h 18mORH-MCO
$192
7/30Tue
1 stopDelta
4h 49mORD-ORH
8/13Tue
1 stopDelta
7h 02mORH-ORD
$198
7/9Tue
1 stopDelta
6h 29mORD-ORH
7/15Mon
1 stopDelta
6h 58mORH-ORD
$204

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Recent one-way flight deals

8/27Tue
nonstopAmerican Airlines
1h 10mJFK-ORH
$69
7/23Tue
nonstopJetBlue
3h 04mFLL-ORH
$74
6/18Tue
nonstopAmerican Airlines
1h 07mJFK-ORH
$79
7/18Thu
nonstopJetBlue
2h 55mMCO-ORH
$84
7/3Wed
nonstopJetBlue
3h 07mFLL-ORH
$89
10/20Sun
nonstopAmerican Airlines
1h 11mJFK-ORH
$89
7/23Tue
2 stopsAmerican Airlines
22h 25mFLL-ORH
$94
8/13Tue
1 stopDelta
4h 49mORD-ORH
$98
7/23Tue
1 stopDelta
4h 57mMCO-ORH
$98
7/2Tue
1 stopDelta
6h 45mORD-ORH
$99

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Last minute flights to Winchester

Last minute flight, train and bus deals

6/14Fri
nonstopJetBlue
3h 07mFLL-ORH
6/22Sat
nonstopJetBlue
3h 14mORH-FLL
$273
6/14Fri
nonstopJetBlue
3h 07mFLL-ORH
6/21Fri
nonstopJetBlue
3h 14mORH-FLL
$283
6/15Sat
nonstopAmerican Airlines
1h 07mJFK-ORH
6/20Thu
nonstopAmerican Airlines
1h 18mORH-JFK
$293
6/17Mon
nonstopJetBlue
3h 07mFLL-ORH
7/19Fri
nonstopJetBlue
3h 12mORH-FLL
$299
6/17Mon
multi-stopAmerican Airlines
16h 56mFLL-ORH
6/20Thu
multi-stopAmerican Airlines
19h 29mORH-FLL
$306
6/14Fri
multi-stopDelta
6h 45mFLL-ORH
6/18Tue
multi-stopDelta
7h 25mORH-FLL
$322
6/16Sun
multi-stopDelta
7h 00mFLL-ORH
6/20Thu
multi-stopDelta
7h 25mORH-FLL
$331
6/17Mon
multi-stopDelta
6h 45mORD-ORH
6/20Thu
multi-stopDelta
7h 56mORH-ORD
$333
6/13Thu
nonstopAmerican Airlines
1h 07mJFK-ORH
6/16Sun
nonstopAmerican Airlines
1h 18mORH-JFK
$358
6/14Fri
nonstopJetBlue
3h 07mFLL-ORH
6/15Sat
nonstopJetBlue
3h 14mORH-FLL
$374

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Flights to Winchester