Cheap Flights to Winchester from $30

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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 $60 and $30 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Jan 23 - Sun, Jan 25
MCO
Orlando Intl.
BNA
Nashville Intl.
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 23 from Orlando Intl. to Nashville Intl., returning Sun, Jan 25, priced at $60 just found
OriginDestinationTravel DatesFlights From*
ORDChattanoogaDecember 5 to December 7$193
RDUHuntsvilleNovember 27 to December 10$199
SEANashvilleDecember 13 to December 16$199
DCAHuntsvilleDecember 4 to December 25$209
IAHHuntsvilleJanuary 9 to January 12$209
RDUChattanoogaJanuary 30 to February 1$247
PHLHuntsvilleNovember 24 to December 9$249
IAHChattanoogaDecember 19 to January 2$253
LAXHuntsvilleJanuary 24 to January 25$283
DCAChattanoogaDecember 12 to December 15$291
SEAHuntsvilleFebruary 7 to February 10$309
SFOChattanoogaNovember 27 to December 4$349
DALHuntsvilleDecember 25 to January 1$351
DFWChattanoogaJanuary 1 to January 7$364
FCOHuntsvilleNovember 20 to November 25$738
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
PHLNashvilleNovember 15 to November 17$182
SFONashvilleNovember 15 to November 20$266
RDUHuntsvilleNovember 15 to December 3$268
IAHNashvilleNovember 15 to November 15$275
PHLChattanoogaNovember 15 to November 19$311
IAHChattanoogaNovember 15 to November 24$314
DCAHuntsvilleNovember 15 to November 19$348
DCANashvilleNovember 15 to November 19$350
LAXHuntsvilleNovember 16 to November 23$404
SEAHuntsvilleNovember 15 to November 26$404
DCAChattanoogaNovember 15 to November 27$485
RDUChattanoogaNovember 15 to November 16$507
SEANashvilleNovember 15 to November 28$515
FCOHuntsvilleNovember 14 to November 25$817
FCONashvilleNovember 16 to November 23$973
*Prices include taxes and fees

Winchester Flight Information

Traveling to
Winchester
Lowest Price
$60
Number of Airlines Serving
Airlines Serving
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

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
$93 nightly
The price is $106 total per night from Nov 16 to Nov 17
$106 total
Nov 16 - Nov 17
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 ...
8.6/10 Excellent! (650 reviews)
very good

Reviewed on Nov 3, 2025

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.
Caption by Hyatt Downtown Nashville/The Gulch

Caption by Hyatt Downtown Nashville/The Gulch

3 out of 5
Price was $860, price is now $595 per person
$595
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Nashville (BNA)
The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
Save 100% on your flight
Price was $928, price is now $603 per person
$603
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Nashville (BNA)
Memoir Wedgewood Houston

Memoir Wedgewood Houston

4 out of 5
Price was $839, price is now $607 per person
$607
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Nashville (BNA)
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Need a Car For After Your Flight?

Midsize

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$36

$116 total
found 2 days ago
Midsize undefined

Special

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$36

$116 total
found 2 days ago
Special undefined

Compact

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$36

$116 total
found 2 days ago
Compact undefined

Standard

  • 5 people
  • Unlimited mileage
Nashville, Tennessee, USA

$37

$118 total
found 2 days ago
Standard undefined
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.

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.