Cheap Flights to Winchester from $34

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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 $76 and $34 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Jan 22 - Fri, Jan 29
SFB
Orlando Sanford Intl.
CHA
Chattanooga Metropolitan
$76 Roundtrip, found 5 days ago
$76
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Jan 22 from Orlando Sanford Intl. to Chattanooga Metropolitan, returning Fri, Jan 29, priced at $76 found 5 days ago
Fri, Dec 4 - Mon, Dec 7
FLL
Fort Lauderdale - Hollywood Intl.
HSV
Huntsville Intl.
$77 Roundtrip, found 10 hours ago
$77
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Fri, Dec 4 from Fort Lauderdale - Hollywood Intl. to Huntsville Intl., returning Mon, Dec 7, priced at $77 found 10 hours ago
OriginDestinationTravel DatesFlights From*
DCANashvilleJanuary 8 to January 11$178
SEAChattanoogaFebruary 9 to February 27$267
LAXChattanoogaDecember 15 to January 5$277
IAHChattanoogaNovember 21 to November 22$314
RDUHuntsvilleDecember 10 to December 15$320
PHLHuntsvilleJanuary 13 to January 17$349
PHLChattanoogaDecember 9 to December 17$359
LAXHuntsvilleNovember 24 to November 26$386
SFOHuntsvilleDecember 3 to December 9$386
SFOChattanoogaDecember 2 to December 5$387
RDUChattanoogaDecember 21 to December 22$425
DCAChattanoogaDecember 16 to December 29$464
DFWChattanoogaDecember 10 to December 14$473
FCONashvilleDecember 7 to December 14$861
FCOHuntsvilleDecember 7 to December 14$890
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
DCANashvilleNovember 14 to November 18$237
ORDNashvilleNovember 13 to November 18$273
DFWNashvilleNovember 14 to November 16$280
ORDHuntsvilleNovember 14 to November 16$314
TTNNashvilleNovember 13 to November 14$328
IAHNashvilleNovember 14 to November 16$348
RDUNashvilleNovember 14 to November 16$354
DCAHuntsvilleNovember 14 to November 21$377
RDUHuntsvilleNovember 13 to November 15$389
LAXNashvilleNovember 14 to November 20$410
SFONashvilleNovember 15 to November 18$430
IAHHuntsvilleNovember 13 to November 15$469
LAXHuntsvilleNovember 13 to November 15$573
SEANashvilleNovember 14 to November 22$772
SEAHuntsvilleNovember 15 to November 20$907
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$76
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

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard Winchester TN
$101 nightly
The price is $116 total per night from Nov 9 to Nov 10
$116 total
Nov 9 - Nov 10
Total with taxes and fees
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
8.8/10 Excellent! (763 reviews)
"I had an issue with the TV and the attendant fixed it right away... very cordial."

Reviewed on Nov 3, 2026

Opens in a new windowBest Western Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Loews Nashville Hotel at Vanderbilt Plaza

Loews Nashville Hotel at Vanderbilt Plaza

4 out of 5
Price was $1,108, price is now $798 per person
$798
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
Noelle

Noelle

4 out of 5
Price was $1,163, price is now $854 per person
$854
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Price was $1,106, price is now $813 per person
$813
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
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Need a Car For After Your Flight?

Economy

  • 4 people
  • Unlimited mileage
Nashville, Tennessee, USA

$35

$107 total
found 1 day ago
Economy undefined

Midsize

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$36

$110 total
found 1 day ago
Midsize undefined

Mini Van

  • 7 people
  • Unlimited mileage
Nashville, Tennessee, USA

$38

$119 total
found 1 day ago
Mini Van undefined

Compact

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$38

$107 total
found 1 day ago
Compact undefined

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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*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.