$324 Cheap flights to City of Winchester

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Cheap flights to City of Winchester from $324 One Way, $690 Round Trip

$690 return flights and $324 one-way flights to City of Winchester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Oct 17 - Mon, Nov 2
BOS
Boston
SOU
Southampton
$690 Roundtrip, found 4 days ago
$690
Roundtrip
found 4 days ago
Select Aer Lingus flight, departing Sat, Oct 17 from Boston to Southampton, returning Mon, Nov 2, priced at $690 found 4 days ago
Wed, Nov 18 - Wed, Nov 25
EWR
New York
SOU
Southampton
$698 Roundtrip, found 12 hours ago
$698
Roundtrip
found 12 hours ago
Select Aer Lingus flight, departing Wed, Nov 18 from New York to Southampton, returning Wed, Nov 25, priced at $698 found 12 hours ago
Mon, Oct 26 - Sun, Nov 8
BOS
Boston
SOU
Southampton
$699 Roundtrip, found 6 days ago
$699
Roundtrip
found 6 days ago
Select Aer Lingus flight, departing Mon, Oct 26 from Boston to Southampton, returning Sun, Nov 8, priced at $699 found 6 days ago
Wed, Nov 18 - Wed, Nov 25
JFK
New York
SOU
Southampton
$703 Roundtrip, found 12 hours ago
$703
Roundtrip
found 12 hours ago
Select Aer Lingus flight, departing Wed, Nov 18 from New York to Southampton, returning Wed, Nov 25, priced at $703 found 12 hours ago
Wed, Nov 18 - Wed, Nov 25
EWR
New York
SOU
Southampton
$707 Roundtrip, found 12 hours ago
$707
Roundtrip
found 12 hours ago
Select Aer Lingus flight, departing Wed, Nov 18 from New York to Southampton, returning Wed, Nov 25, priced at $707 found 12 hours ago
Wed, Nov 18 - Wed, Nov 25
EWR
New York
SOU
Southampton
$711 Roundtrip, found 12 hours ago
$711
Roundtrip
found 12 hours ago
Select Aer Lingus flight, departing Wed, Nov 18 from New York to Southampton, returning Wed, Nov 25, priced at $711 found 12 hours ago
Mon, Sep 21 - Tue, Oct 13
SFO
San Francisco
SOU
Southampton
$806 Roundtrip, found 1 day ago
$806
Roundtrip
found 1 day ago
Select Aer Lingus flight, departing Mon, Sep 21 from San Francisco to Southampton, returning Tue, Oct 13, priced at $806 found 1 day ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
YYZSouthamptonSeptember 19 to September 26$1,157
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic City of Winchester Accommodation Deals

Meon Valley Hotel, Spa & Golf

Meon Valley Hotel, Spa & Golf

4 out of 5
Sandy Lane Southampton England
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $80 total per night from Sep 20 to Sep 21
$80 total
Sep 20 - Sep 21
Total with taxes and fees
Book a stay at this spa hotel in Southampton. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms and the overall value ...
Opens in a new windowMeon Valley Hotel, Spa & Golf
New Place

New Place

4 out of 5
Shirrell Heath Southampton England
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $71 total per night from Oct 15 to Oct 16
$71 total
Oct 15 - Oct 16
Total with taxes and fees
Book a stay at this business-friendly hotel in Southampton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,004 reviews)
"The mansion house was beautiful and the woodland walk was great for walking our dog. Room was clean, but very small, and felt a bit like Butlins. The room was very warm and only one window opened a small amount. We would not want to stay in winter as there was a big gap under the door (which opened ..."

Reviewed on Sep 14, 2026

Opens in a new windowNew Place
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $121 total per night from Oct 11 to Oct 12
$121 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
Opens in a new windowThe Winchester Hotel & Spa
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Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney Winchester England
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $100 total per night from Oct 11 to Oct 12
$100 total
Oct 11 - Oct 12
Total with taxes and fees
Book a stay at this spa hotel in Winchester. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowNorton Park Hotel, Spa & Manor House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

City of Winchester

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Be sure to check our cruise page for free shore excursions, onboard spending, balcony upgrades and other perks. Orbitz offers last-minute, luxury, weekend and summer cruises. You can even designate which port you want to sail from and pre-book on-shore activities. Get there on the cheap with discounts on flights to City of Winchester and City of Winchester flights. Get more bang for your travel buck at Orbitz.

Frequently asked questions

Which airlines fly to City of Winchester?
Look up the deals from the 13 airlines that offer flights to City of Winchester. Whether you'd like to get comfortable in the pointy end of the plane or save cash in economy, they'll have a seat for you. Head for Southampton Airport (SOU) with one of these reputable carriers:

  • Loganair - 107 flights to City of Winchester per month
  • Eastern Airways - 43 flights to City of Winchester per month
  • Aer Lingus - 20 flights to City of Winchester per month

What is the best airport to fly to in City of Winchester?
Touch down at Southampton Airport (SOU), the main entry point to City of Winchester. Organizing your flight to this region doesn't get much easier than that.
How much is a flight to City of Winchester?
If you're looking for flights back and forth, airfares ranged from $690 to $1,157 this past week. The best prices for one-way tickets were $324, coming from Boston (BOS).
How to book the cheapest flight to City of Winchester?
With some of the most amazing flight deals around, you'll always bag a bargain with Orbitz. The following hints and tips will help you land cheap flights to City of Winchester — and leave you with more cash to play with:

  • Taking off from or arriving at other airports may be more affordable. Type in your preferred departure and arrival points. Next, select the 'Nearby airports' function below the form fields to compare your options.
  • If you're flexible with your plans, click on the 'Show flexible dates' option. It'll bring up flight deals for the days either side of your selected departure. Fares often vary depending on what day it is.
  • Select 'Show options' to narrow down your search results. You can choose your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • The early bird gets the biggest savings, so book your tickets the moment you know your travel dates. The most affordable airfares get snapped up first and prices normally increase as the departure date nears.
  • Consider bundling your flights, hotels and car rental into an Orbitz package to save cash.
  • Flying during the busy season can mean pricey airfares. If possible, plan your trip outside of popular dates, such as Easter, Thanksgiving and school breaks.

What is the best time to book a flight to City of Winchester?
Generally speaking, January is the best month to purchase your airfare. This is followed by February and August. Keep this in mind while you browse for a cheap flight to City of Winchester.
What day of the week is the cheapest to book a flight to City of Winchester?
When it comes to cheap flights to City of Winchester, the best days to make a booking are generally Tuesdays, Wednesdays and Saturdays. A rewarding flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to City of Winchester?
If you're on the hunt for cheap flights to City of Winchester, depart earlier in the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday is the most expensive, so avoid flying on this day and do your wallet a favor.
What is the cheapest month to fly to City of Winchester?
We won't keep you guessing — according to Orbitz data, August is generally the most affordable month to fly. Perfect for those who want a weekend getaway or just an escape from it all before the weather turns. The costliest time to fly is in the middle of summer, with airfares at their highest in June.
Which airlines allow free cancellation?
Flexibility is more important than ever, that's why Orbitz lets you search for carriers that won't penalize you for amending your reservation. Enter your departure and arrival points, then select "Filter by flexible change policies." We'll show you options that include free cancellation within 24 hours of booking and no change fees.
What do I need for the flight to City of Winchester?
It's always good to be prepared for anything when going on a trip. Keep in mind the following pointers for a smooth, stress-free flight:

  • In all cases you'll have to show proof of identification. How much? This depends on where you're flying from. When booking your tickets, we suggest to use the same name, birth date and gender as listed on your government-issued ID.
  • Pack some extra entertainment for your long trip to City of Winchester. When you're done watching movies, give your eyes a much-needed break from all that screen time and get stuck into a book.
  • Cabin temperatures can make you shiver. Bring a sweater even if you're vacationing during the height of City of Winchester summer.

How many direct flights are there to City of Winchester?
There are 65 direct flights to City of Winchester every month, so you won't have to deal with any boring stopovers. Book a fare with Loganair or Blue Islands and then sit back and enjoy the flight. Eastern Airways, Aurigny Air Services, Aer Lingus and Flybe also operate nonstop services to City of Winchester.
How do I get cheap first-class/business deals to City of Winchester?
There are ways of booking business or first-class fares to City of Winchester that won't burn a hole through your wallet. Grab a seat at the front of the plane for less with these handy tips:

  • Flexibility is essential. By being open to different travel dates, you'll have more chances of picking up a great deal on your airfares.
  • Find a low-cost airline that has seats in business class. They often come with more legroom and a glass of bubbly — but at a more affordable price.
  • Take advantage of your airline's customer loyalty program and upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

What is the best time to go to City of Winchester?
City of Winchester is a wonderful vacation destination year-round, but the most popular months are January, March and September. If you prefer warm weather, consider heading there in summertime. Like most destinations in the Northern Hemisphere, the summer season kicks off June 20. During this time, temperatures generally drift between 55 ºF and 70 ºF during the day.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.