Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Winchester?

The cheapest prices found with in the last 7 days for return flights were $57 and $39 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Origin Destination Travel Dates Flights From*
MCO Baltimore May 20 - May 23 $57
MCO Sterling May 20 - May 23 $80
BOS Washington Aug 17 - Aug 19 $99
ATL Baltimore Jun 9 - Jun 15 $105
MIA Baltimore May 20 - May 24 $105
TPA Washington Jun 3 - Jun 7 $123
TPA Baltimore Jun 4 - Jun 7 $126
DFW Baltimore Aug 4 - Aug 10 $135
DEN Washington May 29 - Jun 1 $162
LAX Baltimore Aug 18 - Aug 22 $200
DFW Washington Aug 17 - Sep 1 $219
DFW Sterling Aug 17 - Sep 1 $241
FCO Sterling Jun 21 - Sep 8 $409
FCO Washington Jun 6 - Jun 20 $560
FCO Baltimore Aug 13 - Sep 1 $613
*Prices include taxes and fees
Origin Destination Travel Dates Flights From*
MCO Washington May 15 - May 23 $157
DEN Washington May 15 - May 22 $216
DFW Baltimore May 16 - May 19 $265
DEN Sterling May 15 - May 16 $275
TPA Washington May 15 - May 24 $307
MIA Washington May 15 - May 26 $309
MIA Sterling May 15 - May 30 $314
LAX Sterling May 15 - May 25 $329
ATL Sterling May 16 - May 16 $333
DFW Sterling May 16 - May 29 $389
LAX Baltimore May 16 - May 25 $405
LAX Washington May 15 - May 24 $449
SFO Washington May 16 - May 20 $490
SFO Sterling May 15 - May 16 $642
SFO Baltimore May 15 - May 16 $807
*Prices include taxes and fees

Flight Review

Mar 12, 2020

Paid for wifi but it didn't work

Mar 12, 2020

Enjoyed the flight - smooth!

Mar 11, 2020

Most happy that plane was not full, so seat assignmenr did not matter.

Mar 9, 2020

The pressure in the cabin really hurt my ears.

Mar 8, 2020

The pilot for AA flight 797 from Tampa to Washington DC was outstanding!

Mar 8, 2020

Please allow space for my frequent flyer number so I don’t get assigned the last time to board. If you do, make it more obvious.

Mar 8, 2020

I always have pleasant experiences when flying JetBlue

Mar 7, 2020

American flight attendants very pleasant and helpful. Let me move up to premium seating and also provided an adult beverage at no charge.

Mar 5, 2020

Thank you for the cleanliness & ease of transportation.

Mar 5, 2020

I do not like that I was not able to choose my own seats

Mar 3, 2020

Flight was quick and early.

Mar 2, 2020

Flight was delayed about 2 hours because of mechanical problems.

Find The Perfect Hotel For After Your Flight

Amazing Winchester Accommodation Deals

See all 113 Properties in Winchester

Luxury Hotels in Winchester

See all 113 Properties in Winchester

Family Friendly Hotels in Winchester

See all 113 Properties in Winchester

Need a Car For After Your Flight?


Winchester Flight Information

Traveling toWinchester
Lowest Price$57
Number of Airlines Serving
Airlines ServingSpirit Airlines
Number of Daily Flights
Airlines with Direct Flights

FAQs about Winchester Flights

Can I catch a flight to Winchester at the moment?

Before committing to fly to Winchester, be sure to check out our Covid-19 Travel Advisor to see if there are any quarantine requirements or travel restrictions currently in place.

Which airlines fly to Winchester?

All geared up to explore the world? Hoping to kick off your adventure in Winchester? Just a few of the 20 air carriers that fly here are:

  • United Airlines
  • American Airlines
  • Southwest Airlines
If I am not able to travel due to COVID-19, can I change my booking to a later date?

For more info about changing your flight to Winchester, please visit our Customer Service Portal.

What airport is best to fly into Winchester?

Booking your airfare to Winchester is simple, as it has just one airport. You'll find Washington Dulles Intl. Airport (IAD) around 40 mi from all the action downtown.

Where to stay in Winchester

When Winchester starts whispering your name, it’s time to heed the call and reserve a fabulous place to stay with Travelocity. There are 46 accommodations in this wonderful destination for you to look into.

There's nothing more exciting than organizing your accommodations for your next vacation. But after hours of comparing amenities and prices, it can get a little tedious. So why not take our advice and choose one of our recommended properties, like The George Washington Hotel, A Wyndham Grand Hotel and the Wingate by Wyndham Winchester?

Places to visit in Winchester

You're sure to find the perfect gifts and souvenirs for your family and friends back home at Apple Blossom Mall. Make sure you buy yourself a few treats, too! Like some more ideas? Bring the family for an afternoon of fun at Jim Barnett Park, a recreation park. But that's not all there is. Let the youngsters move around and amuse themselves in the exhibits at Shenandoah Valley Discovery Museum. It doesn't get any more interactive and entertaining than that!

How to get through airport security fast when traveling to Winchester

These handy tips and pointers about airport security procedures will save you a lot of time on your way to Winchester:

  • Keep your passport and boarding pass somewhere handy. They'll be the first things you'll be instructed to produce by security personnel.
  • You'll have to stop the music for a little while. Earphones and headphones need to be removed and placed in a bin for X-raying. The same goes for items such as coins and keys.
  • Laptops, tablets and other electronic devices must be placed in a tub to be X-rayed.
  • Flying with your favorite cologne? As long as it's not bigger than 3.4 ounces (100 milliliters) and it's placed in a clear zip-lock bag, you can keep it in your hand luggage.
  • Security personnel may instruct you to take off your shoes in preparation for entering the body scanner. Wear a pair that you can slip off easily. There's nothing more irritating than having to do your laces up again and again.
  • Pocketknives and corkscrews are not allowed on board the aircraft. Tuck them away in your checked luggage to avoid leaving them at the security checkpoint.
*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.