Find flights
When to book
FAQs & Tips
Airlines
Deals

Find cheap flights to Winchester from $69

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 6/30. 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.
1 adult
0 bags
Mon 7/1
Mon 7/8

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

In the last 7 days travelers have searched 42,787,818 times on KAYAK, and here is why:

Save 21% 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.

Good to know

Low season

February

High season

June

Cheapest flight

$69
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 3% 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 09m
    Flights from New York1h 10m
    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 $192.

  • 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 10419 reviews
8.0Entertainment
7.4Food
8.2Boarding
7.9Comfort
8.6Crew
Airline reviews

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

10.0 ExcellentBarb, Jun 2024MSP - JFK
Read more about Delta reviews

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!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

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.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Nothing, terrible travel experience due to weather and maintenance delays and was left stranded in Austin.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Book Cheap Winchester Plane Tickets

Recent round-trip flight deals

6/21Fri
nonstopDelta
1h 16mLGA-ORH
6/25Tue
nonstopDelta
1h 12mORH-LGA
$133
8/1Thu
nonstopJetBlue
3h 04mFLL-ORH
8/5Mon
nonstopJetBlue
3h 12mORH-FLL
$142
6/12Wed
nonstopJetBlue
3h 04mFLL-ORH
6/15Sat
nonstopJetBlue
3h 14mORH-FLL
$172
8/10Sat
2 stopsAmerican Airlines
19h 32mFLL-ORH
8/12Mon
2 stopsAmerican Airlines
22h 45mORH-FLL
$173
8/10Sat
nonstopJetBlue
3h 04mFLL-ORH
8/12Mon
nonstopJetBlue
3h 12mORH-FLL
$183
6/17Mon
1 stopDelta
6h 45mMCO-ORH
6/20Thu
1 stopDelta
7h 09mORH-MCO
$192
8/7Wed
2 stopsAmerican Airlines
21h 32mMCO-ORH
8/16Fri
2 stopsAmerican Airlines
21h 11mORH-MCO
$193
8/14Wed
1 stopAmerican Airlines
7h 27mRDU-ORH
8/19Mon
1 stopAmerican Airlines
5h 38mORH-RDU
$194
7/16Tue
2 stopsAmerican Airlines
23h 18mMCO-ORH
7/20Sat
2 stopsAmerican Airlines
23h 29mORH-MCO
$195
6/14Fri
nonstopJetBlue
3h 07mFLL-ORH
6/19Wed
nonstopJetBlue
3h 14mORH-FLL
$198

Search by stops

Search by airline

Search by price

Recent one-way flight deals

6/30Sun
nonstopDelta
1h 16mLGA-ORH
$69
7/23Tue
nonstopJetBlue
3h 04mFLL-ORH
$74
6/12Wed
nonstopJetBlue
2h 53mMCO-ORH
$84
7/23Tue
2 stopsAmerican Airlines
17h 40mFLL-ORH
$93
7/3Wed
1 stopDelta
6h 45mMCO-ORH
$98
6/27Thu
nonstopJetBlue
3h 07mFLL-ORH
$99
7/31Wed
1 stopDelta
5h 14mRDU-ORH
$99
7/1Mon
1 stopDelta
6h 45mFLL-ORH
$108
8/15Thu
2 stopsAmerican Airlines
20h 51mRDU-ORH
$109
6/8Sat
1 stopAmerican Airlines
17h 31mORD-ORH
$160

Search by stops

Search by airline

Search by price

Last minute flights to Winchester

Last minute flight, train and bus deals

6/6Thu
multi-stopAmerican Airlines
7h 36mMCO-ORH
6/7Fri
multi-stopAmerican Airlines
10h 18mORH-MCO
$225
6/6Thu
nonstopDelta
1h 11mLGA-ORH
6/9Sun
nonstopDelta
1h 12mORH-LGA
$263
6/6Thu
multi-stopDelta
5h 43mRDU-ORH
6/10Mon
multi-stopDelta
6h 26mORH-RDU
$292
6/5Wed
nonstopJetBlue
2h 50mMCO-ORH
6/10Mon
nonstopJetBlue
3h 14mORH-MCO
$298
6/5Wed
multi-stopDelta
7h 01mMCO-ORH
6/10Mon
multi-stopDelta
7h 09mORH-MCO
$312
6/3Mon
multi-stopAmerican Airlines
20h 53mMCO-ORH
6/7Fri
multi-stopAmerican Airlines
19h 10mORH-MCO
$318
6/5Wed
multi-stopAmerican Airlines
20h 59mMCO-ORH
6/10Mon
multi-stopAmerican Airlines
23h 35mORH-MCO
$320
6/6Thu
nonstopJetBlue
2h 53mMCO-ORH
6/7Fri
nonstopJetBlue
3h 14mORH-MCO
$328
6/5Wed
multi-stopJetBlue
8h 45mTPA-ORH
6/12Wed
multi-stopJetBlue
5h 50mORH-TPA
$487
6/6Thu
multi-stopJetBlue
9h 45mLGA-ORH
6/9Sun
multi-stopJetBlue
8h 40mORH-LGA
$783

Search by stops

Search by airline

Search by price

Flights to Winchester