Cheap Flights to Winchester from $29
Wander Wisely with exceptional service, 24/7 supportOpens in a new window
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 $58 and $29 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* |
|---|---|---|---|
| RDU | Chattanooga | January 20 to January 21 | $177 |
| RDU | Huntsville | January 17 to January 28 | $199 |
| DCA | Huntsville | January 15 to January 17 | $214 |
| IAH | Huntsville | January 13 to January 27 | $229 |
| IAH | Chattanooga | January 12 to January 19 | $249 |
| PHL | Huntsville | December 31 to December 31 | $254 |
| SEA | Chattanooga | January 13 to January 21 | $269 |
| LAX | Chattanooga | February 11 to February 14 | $274 |
| LAX | Huntsville | March 11 to March 25 | $293 |
| SFO | Huntsville | January 21 to January 28 | $309 |
| DCA | Chattanooga | January 27 to January 30 | $333 |
| DAL | Huntsville | March 10 to March 17 | $387 |
| DFW | Chattanooga | December 31 to January 1 | $440 |
| FCO | Nashville | March 11 to March 15 | $667 |
| FCO | Huntsville | December 31 to May 30 | $1,007 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| RDU | Huntsville | December 26 to January 1 | $316 |
| RDU | Chattanooga | December 27 to January 13 | $348 |
| IAH | Huntsville | December 26 to January 13 | $352 |
| LAX | Huntsville | December 27 to January 10 | $358 |
| DCA | Huntsville | December 27 to January 5 | $362 |
| RDU | Nashville | December 27 to December 30 | $369 |
| PHL | Chattanooga | December 26 to December 29 | $381 |
| LAX | Chattanooga | December 27 to January 5 | $390 |
| PHL | Huntsville | December 26 to December 31 | $429 |
| DCA | Chattanooga | December 27 to January 14 | $458 |
| DCA | Nashville | December 26 to January 3 | $467 |
| SFO | Nashville | December 26 to January 28 | $492 |
| DFW | Huntsville | December 27 to December 30 | $576 |
| SEA | Huntsville | December 26 to December 31 | $582 |
| FCO | Huntsville | December 27 to March 10 | $982 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $58 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Family Friendly Hotels in Winchester
Best Western Inn
Clean room. Quiet - no fans unkess I turned it on. Convenient parking and ice close to rokm.
Reviewed on Dec 18, 2025
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Need a Car For After Your Flight?
Economy
$25
Compact
$26
Midsize
$26
Special
$27
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!
Explore More Ways to Travel with Travelocity
- Hotels near Tims Ford State Park
- Hotels near Tims Ford Lake
- Hotels near Cowan Railroad Museum
- Chalets in Huntland
- Huntland Hotels
- Motels in Huntland
- Cabins in Decherd
- Extended Stay Hotels in Decherd
- Convention Center Hotels in Decherd
- Decherd Hotels
- Motels in Decherd
- Vacation Homes in Decherd
- Rv Parks in Decherd
- Apartments in Estill Springs
- B&B in Estill Springs
- Cabins in Estill Springs
- Cottages in Estill Springs
- Extended Stay Hotels in Estill Springs
- Cheap Hotels in Estill Springs
- Estill Springs Hotels
- Motels in Estill Springs
- Vacation Homes in Estill Springs
- Rv Parks in Estill Springs
- Cabins in Cowan
- Cowan Hotels
- Motels in Cowan
- Hotels near Lake Cheston
- Apartments in Tullahoma
- Cabins in Tullahoma
- Extended Stay Hotels in Tullahoma
- Hotels with Hot Tubs in Tullahoma
- Hotels with an Indoor Pool in Tullahoma
- Tullahoma Hotels
- 5 Star Hotels in Belvidere
- Farmstay in Belvidere
- Apartments in Belvidere
- Cabins in Belvidere
- Belvidere Hotels
- Vacation Homes in Belvidere
- Hotels near University of the South
- Hotels near Elk River Dam
- Apartments in Sewanee
- B&B in Sewanee
- Cabins in Sewanee
- Chalets in Sewanee
- Cheap Hotels in Sewanee
- Hotels with Bar in Sewanee
- Sewanee Hotels
- Motels in Sewanee
- Vacation Homes in Sewanee
- Resorts in Sewanee
- Hotels near Tim's Ford Marina
- Hotels near Sewanee Golf and Tennis Club
- Flights to Murfreesboro
- Flights to Manchester
- Flights to McMinnville
- Flights to Culleoka
- Flights to Smithville
- Flights to Lynchburg
- Flights to Bell Buckle
- Flights to Chapel Hill
- Flights to Normandy
- Flights to Rock Island
- Flights to Soddy-Daisy
- Flights to Huntland
- Flights to Jasper
- Flights to Campaign
- Flights to Pulaski
- Flights to Woodbury
- Flights to Grundy County
- Flights to Shelbyville
- Flights to Lookout Mountain
- Flights to Chattanooga
- Flights to Flintville
- Flights to Kimball
- Flights to Monteagle
- Flights to Ardmore
- Flights to Quebeck
- Flights to Tullahoma
- Flights to Guild
- Flights to Gruetli Laager
- Flights to Pelham
- Flights to Sewanee
- Flights from Denver to Sewanee
- Flights from Greenville to Sewanee
- Flights from Oklahoma City to Sewanee
- Flights from Bristol to Sewanee