Cheap Flights to Winchester from $24
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 $46 and $24 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* |
|---|---|---|---|
| LAX | Nashville | October 12 to October 13 | $246 |
| DCA | Huntsville | October 28 to November 2 | $279 |
| IAH | Huntsville | August 26 to September 2 | $283 |
| IAH | Chattanooga | September 10 to September 17 | $312 |
| PHL | Huntsville | September 29 to October 3 | $319 |
| SFO | Chattanooga | October 6 to October 21 | $321 |
| DAL | Huntsville | October 14 to October 17 | $335 |
| LAX | Chattanooga | September 16 to September 23 | $336 |
| LAX | Huntsville | September 9 to September 23 | $343 |
| DAL | Chattanooga | October 3 to October 10 | $365 |
| RDU | Chattanooga | September 9 to September 13 | $372 |
| SEA | Chattanooga | September 18 to September 26 | $373 |
| DCA | Chattanooga | September 26 to September 28 | $443 |
| FCO | Nashville | September 23 to September 30 | $768 |
| FCO | Huntsville | September 18 to September 25 | $1,105 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| ORD | Huntsville | August 15 to August 17 | $254 |
| ORD | Chattanooga | August 15 to August 16 | $323 |
| TTN | Nashville | August 16 to August 19 | $353 |
| DCA | Nashville | August 15 to August 21 | $360 |
| RDU | Nashville | August 16 to August 20 | $373 |
| PHL | Huntsville | August 16 to August 23 | $384 |
| DCA | Huntsville | August 14 to August 15 | $394 |
| LAX | Nashville | August 14 to August 18 | $399 |
| PHL | Chattanooga | August 14 to August 17 | $414 |
| LAX | Chattanooga | August 14 to August 15 | $465 |
| IAH | Chattanooga | August 15 to August 16 | $514 |
| IAH | Nashville | August 16 to August 20 | $547 |
| SFO | Nashville | August 16 to August 20 | $561 |
| SEA | Nashville | August 16 to August 22 | $681 |
| DFW | Huntsville | August 16 to August 19 | $1,053 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $46 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Allegiant Air |
Number of Daily Flights | |
Airlines with Direct Flights |
Find The Perfect Hotel For After Your Flight
Family Friendly Hotels in Winchester
Best Western Inn
"We were not so pleased that our room was not serviced even with towels."
Reviewed on Aug 7, 2026
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Winchester flight + hotel packages - premium economy flights
Winchester flight + hotel packages - first class flights
Need a Car For After Your Flight?
Special
$39
Compact
$40
Economy
$40
Midsize
$41
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
- Aparthotels in Decherd
- Cabins in Decherd
- Hotels in Cowan
- Cabins in Cowan
- Hotels in Decherd
- Motels in Decherd
- Privatevacationhomes in Decherd
- Downtown Chattanooga Hotels
- Bedandbreakfast in Estill Springs
- Cabins in Estill Springs
- Cottages in Estill Springs
- Motels in Estill Springs
- Privatevacationhomes in Estill Springs
- Hotels near Fall Creek Falls State Park
- Hotels in Fayetteville
- Inns in Franklin County
- Hotels near Jack Daniel's Distillery
- Hotels in Lynchburg
- Aparthotels in Manchester
- Hotels in Manchester
- Hotels in McMinnville
- Hotels in Monteagle
- Hotels in Murfreesboro
- Hotels in Pelham
- Apartments in Sewanee
- Bedandbreakfast in Sewanee
- Cabins in Sewanee
- Budget in Sewanee
- Hotels in Sewanee
- Motels in Sewanee
- Hotels in Shelbyville
- Hotels near Tennessee Aquarium
- Hotels near Tims Ford Lake
- Hotels in Chattanooga
- The Read House Hotel
- The Hotel Chalet At The Choo Choo
- Hot Tub in Chattanooga
- Hotels near Chattanooga Convention Center
- Hotels near Bonnaroo Music & Arts Festival
- Hotels in Belvidere
- Cabins in Belvidere
- Apartments in Belvidere
- Agritourism in Belvidere
- Caravanparks in Winchester
- Motels in Winchester
- Hotels in Winchester
- Lg lakefront family home with a covered dock and jet-ski port Nicely remodeled
- Lakeshore Modern Lake front with platform dock and 2 kayaks firepit and views
- Aparthotels in Winchester
- Condos in Winchester
- Bedandbreakfast in Winchester
- Apartments in Winchester
- Hotels in Tullahoma
- The Smokehouse Lodge And Cabins
- The Sewanee Inn
- Red Roof Inn Monteagle - I-24
- Quality Inn Decherd - Winchester
- Lynchburg Country Inn
- Hot Tub in Tullahoma
- FIREFLY FARMHOUSE IN NOSTALGIC PASTORAL SETTING
- Budget in Tullahoma
- Secluded Scandinavian Style Cabin 20 private acres View Hot Tub Game Room
- Aparthotels in Tullahoma
- Hotels near Tims Ford State Park
- Hotels near Tim's Ford Marina
- Flights to Woodbury
- Flights to Tullahoma
- Flights to Soddy-Daisy
- Flights to Smithville
- Flights to Shelbyville
- Flights to Sewanee
- Flights from Denver to Winchester
- Flights from Houston to Winchester
- Flights from Kansas City to Winchester
- Flights to Sale Creek
- Flights to Rock Island
- Flights to Pulaski
- Flights to Pelham
- Flights to Murfreesboro
- Flights to Monteagle
- Flights to McMinnville
- Flights to Manchester
- Flights to Lookout Mountain
- Flights to Kimball
- Flights to Jasper
- Flights to Chattanooga
- Flights to Chapel Hill
- Flights to Ardmore