$96 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 7/29. 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 Flight Deals 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.

Recent round-trip flight deals to Winchester

KAYAK's recommended round-trip deals from the most popular airlines that fly to Winchester.
Discover the best prices for you by selecting your travel dates on KAYAK.
WestJet Logo
3:00 pm - 5:25 amLAX-YOW
11h 25m2 stops
WestJet Logo
6:10 am - 2:12 pmYOW-LAX
11h 02m2 stops
$225WestJet
Find Deal
Sun, Aug 3 - Sat, Aug 9
WestJet Logo
6:05 pm - 6:45 amLAX-YOW
9h 40m1 stop
WestJet Logo
12:20 pm - 9:47 pmYOW-LAX
12h 27m2 stops
$230WestJet
Find Deal
Sun, Aug 3 - Sat, Aug 9
Porter Airlines Logo
3:05 pm - 7:38 pmEWR-YOW
4h 33m1 stop
Porter Airlines Logo
3:25 pm - 6:45 pmYOW-EWR
3h 20m1 stop
$244Porter Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
Porter Airlines Logo
3:05 pm - 9:03 pmEWR-YOW
5h 58m1 stop
Porter Airlines Logo
4:10 pm - 5:40 pmYOW-EWR
1h 30mnonstop
$252Porter Airlines
Find Deal
Tue, May 27 - Tue, Jun 3
United Airlines Logo
11:37 pm - 5:06 pmLAX-YOW
14h 29m1 stop
United Airlines Logo
5:15 am - 10:30 amYOW-LAX
8h 15m1 stop
$292United Airlines
Find Deal
Fri, Jul 18 - Wed, Aug 6
Air Canada Logo
10:40 pm - 2:04 pmLAX-YOW
12h 24m1 stop
Air Canada Logo
2:25 pm - 9:35 pmYOW-LAX
10h 10m1 stop
$293Air Canada
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Sun, Jul 20 - Sat, Aug 9
United Airlines Logo
11:59 pm - 2:13 pmLAX-YOW
11h 14m1 stop
United Airlines Logo
7:29 pm - 9:25 amYOW-LAX
16h 56m1 stop
$296United Airlines
Find Deal
Mon, Jul 21 - Mon, Aug 4
Air Canada Logo
12:30 am - 2:04 pmLAX-YOW
10h 34m1 stop
Air Canada Logo
2:25 pm - 9:35 pmYOW-LAX
10h 10m1 stop
$313Air Canada
Find Deal
Wed, Jun 18 - Wed, Jun 25
Air Transat Logo
8:45 am - 10:13 amBOS-YOW
1h 28mnonstop
Air Transat Logo
4:40 pm - 6:08 pmYOW-BOS
1h 28mnonstop
$388Air Transat
Find Deal
Fri, Jul 25 - Fri, Jul 25
Air Transat Logo
3:50 pm - 5:18 pmBOS-YOW
1h 28mnonstop
Air Transat Logo
4:40 pm - 6:08 pmYOW-BOS
1h 28mnonstop
$825Air Transat
Find Deal
Wed, Jun 25 - Fri, Jun 27
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Good to know - Book Cheap Winchester Plane Tickets

Low seasonJanuary
High seasonJune
Cheapest flight$96
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Los Angeles to Ottawa

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

Insights shared by verified travelers who flew to Winchester 
Verified travelerFlew with Air CanadaORD-YOWNov 2024
Ottawa, as a small airport is easiest to navigate! Overhead baggage compartments seem to be smaller, and on every flight they seem to need travellers to volunteer to put carryons in checked luggage instead.
MarcFlew with United AirlinesORD-YOWMar 2024
United's fleet of smaller aircraft on this route is very comfortable.
Verified travelerFlew with United AirlinesORD-YOWJan 2024
I always expect issues with United but there doesn't seem to be another airline to use. Advice: Give yourself and extra day to get anywhere - don't be in a hurry to get home either.

FAQs - booking Winchester flights

  • How long is the flight to Winchester?

    Flights from Washington, D.C.1h 34m
    Flights from Fort Lauderdale3h 35m
    Flights from Newark1h 36m
    Flights from Boston1h 28m
    Flights from Orlando3h 18m
  • What is the cheapest flight to Ottawa?

    In the last 3 days, the cheapest flight deal to Ottawa was found on the route from Los Angeles, at $225 return. The most popular connection is from Newark to Ottawa and KAYAK users have found round-trip deals for as low as $244 in the last 3 days.

  • Which airlines fly to Ottawa?

    Many airlines fly to Ottawa, the most common ones being United Airlines, Porter Airlines, and Air Canada. See the amount of flights per week for popular airlines flying to Ottawa.

  • How to fly to Winchester?

    You cannot fly directly to Winchester. KAYAK recommends you fly to Ottawa (YOW) (22.13 miles from Winchester). From there you can rent a car or get a taxi.

  • What airports are near Winchester?

    The closest airport is Ottawa (YOW) (22.13 mi). Other nearby airports are Ogdensburg (OGS) (29.2 mi), Saranac Lake Adirondack (SLK) (74.74 mi) or Montreal Pierre Elliott Trudeau Intl (YUL) (81.92 mi). KAYAK recommends you fly to Ottawa.

  • How far is Ottawa Airport from central Ottawa?

    The city center of Ottawa is 7 miles from Ottawa Airport.

  • What is the name of Ottawa’s airport?

    There is only 1 airport in Ottawa, called Ottawa Airport (YOW). It can also be referred to as Macdonald–Cartier Intl, Ottawa, or Ottawa Macdonald-Cartier 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 Ottawa Airport.
  • Looking for cheap airfare to Winchester? 25% of our users found round-trip tickets to Winchester for the following prices or less: From Las Vegas $193, from Boston $231
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Winchester flight deals.

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
Porter AirlinesOverall score based on 285 reviews
7.6Food
8.2Boarding
8.8Crew
8.1Comfort
7.0Entertainment
Airline reviews

I love the 2 seats per row. More room. The crew were excellent.

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

I love the 2 seats per row. More room. The crew were excellent.

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

Over the wing seat at emergency exit only downside people using lavatory have no respect and wait in the space

Flight delayed any hour and couple of big gate changes

The pilot came out and chatted with the passengers. He explained why there was a slight delay. The crew was excellent. Very helpful. I had to buy meals for my whole family and they were in different seats, so the crew had to deal with that. They were very pleasant and accommodating and did a great job!

We were unable to land in Liberia. It was not the airline’s fault, but we had to be diverted to SJO.

We had things stolen from our luggage, we also were refused an upgrade on a flight that was not full.

When we left, it wasn't Great . People were drinking heavily, very disrespectful Extremely loud, the entire trip. I think the crew members, should have get their attention. Coming back was great.

I sat in the club. The seeds were fantastic. The meal was great and Entertainment was good. The crew was fantastic. I recommend it to everybody.

The food was small portions and not fresh. I was seated at the back of the plane so by the time the cart approached me most of the food options were sold out. The cabin crew was fantastic however.

Great flight and crew. Food isn't free and neither are headphones...

We were in economy class but paid for option Plus which offer you an extra snack after take off, free earplugs & blanket. The crew were very attentive. The comfort however wasn’t great, hard to be comfortable in such restraint place. Wasn’t able to sleep through out the 7hrs flight and was exhausted upon arrival.

Everything is good except the dinner and breakfast. The sandwich is very delicious. Toilet is clean, I only use one of them. Flight attendants are very nice. 👍👍

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Multiple delays and not straight answer from the United team

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Stewardess spilled orange juice on my clothes/seat no help no apology just threw napkins at me to clean the mess up. Not Happy.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

The plane pushed back from the gate on time. However, it stopped on the ramp, and we waited for over 20 minutes before the aircraft pulled back to the gate. Apparently, something of importance had to be removed from the aircraft by the gate agent. I found this to be odd. The delay was not significant, but I felt that whatever was on the aircraft that had to be taken off, should’ve been done before we pushed back from the gate.

I didn’t get on plane. Passport being processed by consulate with visa application. Tried to cancel through underpricer after purchasing cacelling for any reason. No dice, they are thieves.

Electric plugs didn't work. Entertainment system wasn't working

The staff were the friendliest I have encountered in years. Absolutely great!

Plane changed to one with no entertainment system or ability to serve hot meals

Flight was delayed 3 times. Then cancelled due to pilot being timed out. They refused hotel vouchers. Gate attendants were very rude and could not help you at all.

No access to any entertainment No food other than a cookie or pretzels even tho flight was over the supper hour Seats very close together and very little leg room Staff was very good

Good. Would be better if the carry on baggage was free.

Horrible. I checked out myself that it seems that I can have a free carry-on. But they ask me to pay $75 when we are nearly boarding. It was tricky during check out that make you mistake that you can have a carry-on beside your personal item. Also they ask $75 in the airport instead of $35 during checkout. So the whole process is designed to make you this mistake

Westjet is one of the worst airlines in the world. 100% guaranteed to have flight delays and flight cancellations. Will never book again with Westjet.

Plane should have entertainment, instead of people paying to use wifi

Westjet has been absolutely terrible! Flights continually cancelled. Took 4 days to get home. Would have been 5, but we booked last flight with another airline after our Westjet flight was cancelled. Even pilot on original flight looked frustrated! Funny how they say cancelation is weather related, but they still have more than 1 other flight leaving to same destination on same day, but of course those are all full. This happened more than once on this trip. Two weather related cancelations and 1 mechanical. Not sure if the last flight even went ahead. Felt so sorry for families with kids and babies, and the older travellers. Felt like we lived out of suitcases and airports for days - SO RIDICULOUS! Next to no help from Westjet staff at airports, but it appears there is nothing they can help you with. Westjet has made it that they are unreachable when you need them! People were getting extremely frustrated, and rightfully so. Additional costs to us really added up, but Westjet literally DOESN'T CARE! Final straw was when we had to pay $1280 on a different airline (economy) trying to get home after another cancelled flight. Westjet will be refunding us a whole $140! Can't believe how this airline operates. We will never, ever use them again!

The only thing I didn’t like was how far away the gate was. I would have requested a wheelchair had I known.

2.5 hour delay sitting in the plane on the tarmac, you tell me how the experience was

I hope these comments will find their way to AC customer experience team. Me and my spouse 50 years of aged coming back from 7 days perfect vacation... While boarding in FLL flight AC1621, one of the boarding agents (tall aged african american) man literelly yeld at my wife during the picture talking process. MAM ! STEP !! BACK !!! We are not illegal immegrants beying deported, nor are we in the millitary. We are customers returning home. This was unacceptable. While boarding in YYZ flight AC1154, one of the boarding agents (tall aged caucasian) man criticied with several complesant remarks my passport condition saying that I could not travel intl with it due to stain, decoloration, and BLOOD. My passport does not have blood on it! Yes it might be in less than perfect condition, but their are ways to talk to customer that does not imply not allow a boarding agent to be angry fathery like, or a custom agent looking at a suspicious individual. Both experience were less than acceptable for might I remind you a paying CUSTOMER returning home.

This flight didn't happen for me because of overbooking.

Terrible experience, flight was delayed both ways. Limited compensation for the 5+ hour delay. Will not be flying Air Canada Rouge, and don’t recommend you do either.

The boarding was relatively quick, the crew welcoming and flight uneventful. The omission of meals on all airlines is unacceptable especially when the flight is during a mealtime such as this one, (lunchtime), is unacceptable.

Everything was simple and easy. The lady at the gate was super friendly, I wish I had her name to share. She's a little older, dark-haired. You can tell she likes her job and would be a great influence on any young people training with her.

No Charging ports for personal electronics, which were required to use wifi entertainment.

Rushed, the boarding was a great deal like a Chinese fire drill.

it was red eye flight, it was ok, there was beverage service, thats it i didnt care much as i wanted to sleep

Everything went smoothly. I appreciate the selection of free movies.

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