$41 Cheap Flights to Winchester, CA

View $41 flight on Fri, Oct 10, 2025Opens in a new window

Popular airlines to Winchester

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • one key icon

    Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Winchester?

Prices were available within the past 7 days and start at $41 for one-way flights and $82 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Aug 29 - Sun, Aug 31
SFO
San Francisco
SBD
San Bernardino
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Aug 29 from San Francisco to San Bernardino, returning Sun, Aug 31, priced at $82 just found
Frontier Airlines
Sun, Oct 12 - Tue, Oct 14
SFO
San Francisco
PSP
Palm Springs
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Oct 12 from San Francisco to Palm Springs, returning Tue, Oct 14, priced at $108 found 2 days ago
Southwest Airlines
Mon, Oct 27 - Wed, Oct 29
SFO
San Francisco
PSP
Palm Springs
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from San Francisco to Palm Springs, returning Wed, Oct 29, priced at $115 found 2 days ago
Alaska Airlines
Thu, Aug 21 - Mon, Aug 25
SFO
San Francisco
PSP
Palm Springs
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Alaska Airlines flight, departing Thu, Aug 21 from San Francisco to Palm Springs, returning Mon, Aug 25, priced at $117 just found
United
Mon, Oct 6 - Thu, Oct 16
SFO
San Francisco
PSP
Palm Springs
$117 Roundtrip, found 2 hours ago
$117
Roundtrip
found 2 hours ago
Select United flight, departing Mon, Oct 6 from San Francisco to Palm Springs, returning Thu, Oct 16, priced at $117 found 2 hours ago

Find the cheapest month to fly from Columbus (CMH) to Los Angeles (LAX)

August is typically the cheapest month to fly

From $110 - $225 per traveler.

Graph displaying average flight prices per month

Alternative airports near Winchester

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Palm Springs Intl. PSP. Cheapest option available. Average driving time to city center is 58 minutes. Flights from $428
PSP
Palm Springs Intl.
Cheapest
Average driving time to city center58 min
Flights from $428
Select flight to San Bernardino Intl. SBD. Average driving time to city center is 48 minutes. Flights from $979
SBD
San Bernardino Intl.
Average driving time to city center48 min
Flights from $979
Select flight to McClellan-Palomar CLD. Average driving time to city center is 59 minutes. Flights from $537
CLD
McClellan-Palomar
Average driving time to city center59 min
Flights from $537

Tips to find the cheapest flights to Winchester

The cheapest day to fly

Get started finding a cheap flight to Winchester on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

August is the cheapest month to fly to Winchester. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Winchester. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Winchester, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Winchester

The lowest price for round-trip flights to Winchester in 2025 starts from from $82, while one-way tickets start from from $41. Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Winchester. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Winchester

Breeze Airways, Southwest Airlines, Frontier Airlines, Alaska Airlines, United are just some of the airlines that can typically offer cheap tickets to Winchester. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Winchester and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Winchester, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Winchester. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Winchester plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Winchester

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Winchester.

Stopover savings

The cheapest tickets to Winchester are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Winchester. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Winchester for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Winchester. Simply download the free Expedia app to your smart device and activate Winchester flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Winchester. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

Where can I learn more about changing or canceling my flight to Winchester?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
How do I find cheap flights to Winchester that have flexible change policies?
We get that travel plans can change in the blink of an eye, so choosing a flexible airfare with Expedia makes good sense. Tick the "No change fee" box directly below the "Flexible change policies" filter. Your low-cost, flexible flight to Winchester is just a few clicks away.
What is the name of Winchester's airport?
If you're traveling by air, you won't have to worry which airport to choose. Winchester has just one -- San Diego Intl. Airport (SAN).
How many airlines fly to Winchester?
Winchester is serviced by 16 air carriers from 62 airports around the world.
How many nonstop flights are there to Winchester?
With 1,860 nonstop flights each week, you'll be hitting the runway in Winchester before you can say, "Are we there yet?"
Where are the most popular flights to Winchester departing from?
A large number of flights to Winchester take off from Las Vegas, Phoenix and San Francisco airports.
How long is the flight to Winchester Airport?
Which city you depart from determines how much of the in-flight entertainment you'll get to see. From Santa Clara to Winchester, the average flight time is 1 hour and 21 minutes. From Sacramento it usually takes 1 hour and 29 minutes, and from Las Vegas it's 1 hour and 9 minutes.
How to book the cheapest flight to Winchester?
If you'd like to save some cash on your trip to Winchester, then listen up! As every experienced traveler knows, avoid booking at the last minute. Prices are often highest just prior to the departure date. Don't stop there, though. Do some research and see if there are a few airports at your destination. Prices often differ depending on the airport you fly into. Don't forget to compare fares across airlines as well. Last of all, be prepared to lock in your seat quickly if you stumble on a great price. It might not be available for too long. With a bit of knowledge and a little good fortune, the perfect fare will be yours.
How to survive the flight to Winchester?
Depending on where you're coming from, your flight to Winchester could be a breeze or it could drag on forever. We've compiled some useful hints that will help you start your next unforgettable escape on the right foot.What to pack in your hand luggage:

  • Air travel can be a comfortable experience if you've got all the right gear. Firstly, you'll need basic toiletry items, such as a toothbrush and hairbrush, a clean set of clothes and a few magazines. Secondly, leave space in your carry-on bag for your phone, tablet and chargers, any medications and maybe a comfy neck pillow too. Lastly, and most importantly, remember to bring your passport, travel documents and your bank cards.

Do not pack the following items in your hand luggage:

  • While the list of restricted items differs between air carriers, the general rule of thumb is avoid carrying anything sharp, flammable or explosive. This includes screwdrivers, knives, fuels and bleaching agents. Sports equipment like hockey sticks, and objects that could harm passengers, such as swords and batons, are also banned from the cabin.

What to wear on a flight:

  • Your goal here is to make yourself as comfortable as you can. Layer up with loose, breathable clothing and pack a sweater in case it gets chilly in the cabin. Pick flat, slightly roomy shoes as your feet may swell a little during the journey. Leave the stilettos and heavy hiking boots in your luggage.
  • Unfortunately, a risk of flying long-haul is developing deep vein thrombosis (DVT), a blood clot condition caused by extended periods of inactivity. To avoid this, take every opportunity to walk around the cabin and stretch your legs. Compression tights and socks are another great idea to help reduce this risk.

How to get through airport security fast when flying to Winchester?
The answer is --- be prepared. We've rounded up some top tips for an easy trip through airport security. Watch out Winchester, here you come:

  • Airport security personnel first need to establish that you have a valid passport and travel documents before you can proceed any further. Have them ready for inspection.
  • Time to strip down. Well kind of. Your belt, coat, keys and other items in your pocket, like your headphones, will need to go through the X-ray machine. Make your life easier by removing them as it gets closer to your turn.
  • All your electronic gadgets, including your phone and laptop, are also required to be scanned separately.
  • Any gels or liquids, such as perfume or hairspray, that you want to take on board need to be in containers no larger than 3.4 ounces (100 milliliters). Also, they all must fit inside a quart-size (one liter), clear zip-lock bag.
  • Choosing your footwear wisely can save you valuable minutes. Hiking or heavy-style boots are often required to be removed and X-rayed separately. Lightweight sneakers usually aren't.
  • Airlines won't allow any sharp items or pocket knives in your carry-on baggage. If you need to bring these kinds of items, pack them safely in your checked baggage.

Flights to Winchester information
Destination airport
San Bernardino Intl.
Destination airport IATA code
SBD
Destination city name
San Bernardino
Roundtrip price
$81

Trending flights to Winchester

Prices were available within the past 7 days and start at $41 for one-way flights and $82 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Breeze Airways
Fri, Aug 29 - Sun, Aug 31
SFO
San Francisco
SBD
San Bernardino
$82 Roundtrip, just found
$82
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Aug 29 from San Francisco to San Bernardino, returning Sun, Aug 31, priced at $82 just found

Explore a world of travel with Expedia

*Available to One Key members.