Cheap Flights to Winchester from $42
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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 $82 and $42 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* |
|---|---|---|---|
| ORD | Chattanooga | August 4 to August 10 | $249 |
| ORD | Huntsville | August 1 to August 6 | $269 |
| DCA | Huntsville | May 24 to May 30 | $269 |
| IAH | Chattanooga | May 27 to June 3 | $273 |
| RDU | Huntsville | May 29 to May 31 | $284 |
| TTN | Chattanooga | July 22 to July 25 | $296 |
| PHL | Huntsville | May 28 to June 4 | $309 |
| SEA | Chattanooga | June 3 to June 6 | $318 |
| LAX | Chattanooga | July 18 to July 25 | $321 |
| SEA | Huntsville | August 4 to August 18 | $342 |
| LAX | Huntsville | July 9 to July 14 | $346 |
| RDU | Chattanooga | June 15 to June 16 | $406 |
| DCA | Chattanooga | July 24 to July 27 | $421 |
| SFO | Chattanooga | July 30 to August 3 | $429 |
| DFW | Chattanooga | August 12 to August 16 | $483 |
| Origin | Destination | Travel Dates | Flights From* |
|---|---|---|---|
| IAH | Nashville | May 16 to May 24 | $278 |
| PHL | Nashville | May 15 to May 18 | $327 |
| ORD | Chattanooga | May 16 to May 18 | $347 |
| RDU | Nashville | May 16 to May 18 | $357 |
| ORD | Huntsville | May 15 to May 18 | $379 |
| RDU | Huntsville | May 15 to May 18 | $384 |
| IAH | Huntsville | May 15 to May 17 | $388 |
| DCA | Nashville | May 15 to May 21 | $398 |
| LAX | Nashville | May 16 to May 16 | $440 |
| HOU | Chattanooga | May 15 to May 17 | $493 |
| ORD | Nashville | May 17 to May 20 | $526 |
| DCA | Chattanooga | May 15 to May 17 | $591 |
| DFW | Chattanooga | May 15 to May 17 | $593 |
| DFW | Huntsville | May 16 to May 18 | $663 |
| SFO | Huntsville | May 15 to May 17 | $1,950 |
Winchester Flight Information
Traveling to | Winchester |
|---|---|
Lowest Price | $82 |
Number of Airlines Serving | |
Airlines Serving | Breeze Airways |
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 okay. Bathroom caulking poor and walls peeling. Outlet on lights not working
Reviewed on May 6, 2026
Best Winchester Flight and Hotel Packages
Winchester flight + hotel packages - economy flights
Winchester flight + hotel packages - first class flights
Need a Car For After Your Flight?
Compact SUV
$44
Economy
$52
Fullsize Recreational Vehicle
$54
Midsize Pickup Regular Cab
$57
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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