Cheap Flights to Winchester from $269

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How Much Does it Cost To Fly To Winchester?

The cheapest prices found with in the last 7 days for return flights were $530 and $269 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Mon, Oct 20 - Mon, Nov 3
JFK
John F. Kennedy Intl.
SOU
Southampton
$535 Roundtrip, found 5 days ago
$535
Roundtrip
found 5 days ago
Select Aer Lingus flight, departing Mon, Oct 20 from John F. Kennedy Intl. to Southampton, returning Mon, Nov 3, priced at $535 found 5 days ago
OriginDestinationTravel DatesFlights From*
BOSSouthamptonOctober 20 to November 4$530
JFKSouthamptonOctober 20 to November 4$531
FCOSouthamptonDecember 18 to December 26$610
LAXSouthamptonNovember 3 to November 19$663
YYZSouthamptonNovember 10 to November 24$721
SFOSouthamptonNovember 3 to November 10$736
SYDSouthamptonSeptember 29 to October 3$2,674
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
JFKSouthamptonSeptember 21 to October 7$671
LAXSouthamptonSeptember 21 to October 2$881
BOSSouthamptonSeptember 19 to September 21$1,076
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$530
Number of Airlines Serving
Airlines Serving
Aer Lingus
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Winchester Accommodation Deals

Days Inn by Wyndham Winchester M3

Days Inn by Wyndham Winchester M3

2.5 out of 5
Moto Motorway Service Area, Shroner Wood, Winchester, England
$45 nightly
The price is $54 total per night from Sep 21 to Sep 22
$54 total
Sep 21 - Sep 22
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
7.2/10 Good! (811 reviews)
Nice hotel , nice staff
"Our family was traveling internationally and couldn’t make local phone calls when our rental car had a puncture issue, the hotel owner was very nice and helpful to call rental company to arrange road side assistance. Much appreciated!"

Reviewed on Sep 9, 2025

Opens in a new windowDays Inn by Wyndham Winchester M3
Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane, Winchester, England
$51 nightly
The price is $61 total per night from Oct 12 to Oct 13
$61 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this 3-star hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,006 reviews)
"Unusual property, perfect location next to Marwell zoo. Staff very attentive & helpful, especially the receptionist who checked us in. Swimming pool area a little dated, with dangerously slippery floor. Used restaurant for evening meal, food overpriced for what we had, also hot offerings at breakfast ..."

Reviewed on Sep 13, 2025

Opens in a new window Marwell Hotel Winchester South
Winchester Royal Hotel

Winchester Royal Hotel

4 out of 5
St Peter Street, Winchester, England
$124 nightly
The price is $149 total per night from Oct 5 to Oct 6
$149 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this hotel in Winchester. Enjoy breakfast (surcharge), 24-hour room service, and parking (surcharge). Our guests praise the breakfast and the bar in ...
8.2/10 Very Good! (1,004 reviews)
Great hotel with the attractions right on the door
"The review i gave for the first night still stands hotel was clean room with garden view was excellent and the bar plus staff was excellent. Centrally the hotel was next to all the minster and gallerys. Would highly recommend. Our experience was great."

Reviewed on Sep 11, 2025

Opens in a new windowWinchester Royal Hotel
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The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,006 reviews)
"Super friendly staff great comfy and clean room"

Reviewed on Sep 15, 2025

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Opens in a new windowThe Winchester Hotel & Spa
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.

Luxury Hotels in Winchester

Lainston House Hotel

Lainston House Hotel

3.5 out of 5
Woodman Lane, Sparsholt, Winchester, England
Stay at this 3.5-star boutique hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the room service in our reviews. ...
Stately home from home
"Very nice stay in a stately home. Staff are extremely friendly and helpful, and the food is high quality"

Reviewed on Feb 12, 2022

Get rates
Opens in a new windowLainston House Hotel
Hotel du Vin & Bistro Winchester

Hotel du Vin & Bistro Winchester

4 out of 5
Southgate Street, Winchester, England
$150 nightly
The price is $180 total per night from Oct 5 to Oct 6
$180 total
Oct 5 - Oct 6
Total with taxes and fees
Stay at this 4-star eco-certified hotel in Winchester. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
8.8/10 Excellent! (534 reviews)
Excellent staff
"The staff at the hotel couldn’t have been nicer or more helpful, particularly Anka. I’d fallen and cracked my ribs and they immediately brought an ice pack and changed my room so I wouldn’t have as many stairs and did everything possible to help me. The hotel is charming with a beautiful garden and ..."

Reviewed on Sep 13, 2025

Opens in a new windowHotel du Vin & Bistro Winchester
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,006 reviews)
"Super friendly staff great comfy and clean room"

Reviewed on Sep 15, 2025

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Opens in a new windowThe Winchester Hotel & Spa
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voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way Morn Hill, Winchester, England
$93 nightly
The price is $112 total per night from Oct 16 to Oct 17
$112 total
Oct 16 - Oct 17
Total with taxes and fees
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (889 reviews)
"REALLY NICE HOTEL CLEAN CONVENIENT"

Reviewed on Sep 2, 2025

Opens in a new windowvoco Winchester Hotel & Spa by IHG
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.

Family Friendly Hotels in Winchester

Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane, Winchester, England
$51 nightly
The price is $61 total per night from Oct 12 to Oct 13
$61 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this 3-star hotel in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
7.6/10 Good! (1,006 reviews)
"Unusual property, perfect location next to Marwell zoo. Staff very attentive & helpful, especially the receptionist who checked us in. Swimming pool area a little dated, with dangerously slippery floor. Used restaurant for evening meal, food overpriced for what we had, also hot offerings at breakfast ..."

Reviewed on Sep 13, 2025

Opens in a new window Marwell Hotel Winchester South
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way Morn Hill, Winchester, England
$93 nightly
The price is $112 total per night from Oct 16 to Oct 17
$112 total
Oct 16 - Oct 17
Total with taxes and fees
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (889 reviews)
"REALLY NICE HOTEL CLEAN CONVENIENT"

Reviewed on Sep 2, 2025

Opens in a new windowvoco Winchester Hotel & Spa by IHG
The Running Horse

The Running Horse

4 out of 5
88 Main Road, Littleton, Winchester, England
$79 nightly
The price is $95 total per night from Oct 12 to Oct 13
$95 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this 4-star business-friendly inn in Winchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
9/10 Wonderful! (299 reviews)
"Running Horse is very quaint and cozy. The dini g options are very nice and the service natural and friendly. My husband and my inlaws stayed for only one night and were very happy with the accommodations. The countryside is beautiful."

Reviewed on Sep 9, 2025

Opens in a new windowThe Running Horse
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The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane, Winchester, England
Stay at this 4-star spa hotel in Winchester. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,006 reviews)
"Super friendly staff great comfy and clean room"

Reviewed on Sep 15, 2025

Get rates
Opens in a new windowThe Winchester Hotel & Spa
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.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was $1,245, price is now $1,196 per person
$1,196
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Southampton (SOU)
Hampshire Court Hotel & Spa

Hampshire Court Hotel & Spa

4 out of 5
Price was $1,270, price is now $1,247 per person
$1,247
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Southampton (SOU)
Don't see what you're looking for?
See all available trips from Chicago to Winchester
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Winchester?
Packed and ready to travel around the world? Hoping to begin in Winchester? A few of the 20 airlines that fly here include:

  • British Airways
  • Virgin Atlantic
  • Aer Lingus

What airport is best to fly into Winchester?
Before locking in your flight to Winchester, remember it has two airports. LHR is 45 mi from the city center, while Southampton Airport is 8 mi from the downtown area.
Where to stay in Winchester
Whether you're in Winchester on a family vacation, a solo adventure or something else entirely, you'll find the ideal place to lay your head. Book with Travelocity and pick from 203 properties within easy reach of the downtown area.If you're after somewhere fancy to spend your nights, slide between the silky smooth sheets at the Winchester Royal Hotel. Alternatively, look into the Days Inn by Wyndham Winchester M3. It's an attractive choice if you're vacationing on a smaller budget.
Places to visit in Winchester
If you want to check out a couple of the fabulous attractions here, add Great Hall, and Winchester Cathedral to your travel schedule.Winchester Christmas Market is a great place to buy yourself a gift or stroll among the stalls. Want some more options? Inject some culture into your stay by purchasing tickets to a play at Theatre Royal Winchester. And that's not all there is. You'll feel like you've stepped back in time with an excursion to Hospital of St Cross, a historically significant building.
How to get through airport security fast when traveling to Winchester
These useful tips and hints about airport security procedures will save you a lot of time and energy on your way to Winchester:

  • Be sure you know the whereabouts of your boarding pass and passport. You don't want to hold up the queue when you're asked to produce them.
  • Take off your belt, jewellery and shoes before approaching security. Items like these are not permitted to pass through the body scanner.
  • Laptops must be taken out of their protective cases and placed in a tub before being X-rayed.
  • Flying with a new cologne? As long as it contains no more than 3.4 ounces (100 milliliters) and it's stored in a clear resealable plastic bag, you can keep it with you in your hand luggage.
  • Steel-cap footwear and other heavy shoes are usually X-rayed at the security checkpoint. Consider wearing lightweight sneakers instead.
  • Some places have strict quarantine laws. Think about where you're headed to and whether or not you can travel with unpackaged foods.

Plane Tickets To Winchester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winchester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.