Cheap Flights to Winchester from $29
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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 $56 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* |
|---|---|---|---|
| IAH | Nashville | February 20 to February 23 | $168 |
| ORD | Chattanooga | March 13 to March 17 | $194 |
| IAH | Chattanooga | May 3 to May 4 | $197 |
| DCA | Huntsville | April 10 to April 17 | $209 |
| RDU | Huntsville | February 25 to March 4 | $229 |
| IAH | Huntsville | March 11 to March 25 | $229 |
| SEA | Chattanooga | February 28 to March 4 | $257 |
| PHL | Huntsville | March 14 to March 28 | $269 |
| LAX | Huntsville | March 10 to March 31 | $293 |
| SFO | Huntsville | April 1 to April 6 | $327 |
| SFO | Chattanooga | March 10 to March 17 | $329 |
| DCA | Chattanooga | April 7 to April 14 | $340 |
| DAL | Huntsville | April 7 to April 21 | $389 |
| FCO | Nashville | May 16 to May 29 | $678 |
| FCO | Huntsville | March 19 to March 23 | $749 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| IAH | Nashville | February 14 to March 2 | $163 |
| ORD | Huntsville | February 14 to March 2 | $283 |
| ORD | Chattanooga | February 14 to February 15 | $310 |
| IAH | Huntsville | February 13 to February 19 | $311 |
| PHL | Huntsville | February 14 to February 25 | $311 |
| DCA | Huntsville | February 13 to February 21 | $315 |
| DCA | Nashville | February 15 to February 17 | $328 |
| LAX | Chattanooga | February 14 to March 2 | $368 |
| SFO | Huntsville | February 14 to February 17 | $379 |
| RDU | Chattanooga | February 14 to February 26 | $418 |
| SFO | Nashville | February 15 to February 18 | $427 |
| DCA | Chattanooga | February 14 to March 31 | $444 |
| IAH | Chattanooga | February 13 to February 17 | $497 |
| DAL | Huntsville | February 14 to February 17 | $574 |
| FCO | Nashville | February 13 to February 19 | $788 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $56 |
Number of Airlines Serving | |
Airlines Serving | Frontier Airlines, Spirit 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
Room was clean but smelled kinda moldy and musty
Reviewed on Jan 4, 2026
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Winchester flight + hotel packages - premium economy flights
Winchester flight + hotel packages - business class flights
Winchester flight + hotel packages - first class flights
Need a Car For After Your Flight?
Midsize
$44
Compact
$44
Special
$44
Economy
$45
Plane Tickets To Winchester
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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!
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