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Winchester

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Winchester Flights as Low as $86

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Fri, Aug 8 - Fri, Aug 15
ORD
O'Hare Intl.
BNA
Nashville Intl.
$86 Roundtrip, found 22 hours ago
$86
Roundtrip
found 22 hours ago
Select Spirit Airlines flight, departing Fri, Aug 8 from O'Hare Intl. to Nashville Intl., returning Fri, Aug 15, priced at $86 found 22 hours ago
Spirit Airlines
Sun, Jun 15 - Thu, Jun 26
BOS
Logan Intl.
BNA
Nashville Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sun, Jun 15 from Logan Intl. to Nashville Intl., returning Thu, Jun 26, priced at $100 found 1 day ago
Spirit Airlines
Fri, Aug 1 - Mon, Aug 4
CLT
Charlotte-Douglas Intl.
BNA
Nashville Intl.
$100 Roundtrip, found 3 hours ago
$100
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Fri, Aug 1 from Charlotte-Douglas Intl. to Nashville Intl., returning Mon, Aug 4, priced at $100 found 3 hours ago
JetBlue Airways
Sun, Aug 10 - Wed, Aug 20
JFK
John F. Kennedy Intl.
BNA
Nashville Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Aug 10 from John F. Kennedy Intl. to Nashville Intl., returning Wed, Aug 20, priced at $127 found 1 day ago
American Airlines
Tue, Jul 1 - Tue, Jul 1
DFW
Dallas-Fort Worth Intl.
BNA
Nashville Intl.
$134 Roundtrip, found 17 hours ago
$134
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Tue, Jul 1 from Dallas-Fort Worth Intl. to Nashville Intl., returning Tue, Jul 1, priced at $134 found 17 hours ago
American Airlines
Wed, Sep 10 - Sat, Sep 13
ONT
Los Angeles - Ontario Intl.
BNA
Nashville Intl.
$185 Roundtrip, found 3 days ago
$185
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 10 from Los Angeles - Ontario Intl. to Nashville Intl., returning Sat, Sep 13, priced at $185 found 3 days ago
Spirit Airlines
Sun, Jun 15 - Tue, Jun 17
LAX
Los Angeles Intl.
BNA
Nashville Intl.
$201 Roundtrip, just found
$201
Roundtrip
just found
Select Spirit Airlines flight, departing Sun, Jun 15 from Los Angeles Intl. to Nashville Intl., returning Tue, Jun 17, priced at $201 just found
Delta
Tue, Jun 17 - Sat, Jun 21
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$212 Roundtrip, found 1 day ago
$212
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 17 from O'Hare Intl. to Chattanooga Metropolitan, returning Sat, Jun 21, priced at $212 found 1 day ago
Spirit Airlines
Fri, Jun 13 - Mon, Jun 16
BOS
Logan Intl.
CHA
Chattanooga Metropolitan
$235 Roundtrip, found 1 day ago
$235
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Jun 13 from Logan Intl. to Chattanooga Metropolitan, returning Mon, Jun 16, priced at $235 found 1 day ago
Delta
Wed, Aug 6 - Tue, Aug 12
BOS
Logan Intl.
HSV
Huntsville Intl.
$247 Roundtrip, found 1 day ago
$247
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 6 from Logan Intl. to Huntsville Intl., returning Tue, Aug 12, priced at $247 found 1 day ago
Delta
Sat, Jun 7 - Wed, Jun 11
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$251 Roundtrip, found 1 day ago
$251
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Huntsville Intl., returning Wed, Jun 11, priced at $251 found 1 day ago
Delta
Tue, Jul 1 - Tue, Jul 1
DAL
Love Field
BNA
Nashville Intl.
$252 Roundtrip, found 17 hours ago
$252
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Jul 1 from Love Field to Nashville Intl., returning Tue, Jul 1, priced at $252 found 17 hours ago
Bargain Flight
Tue, Jun 3 - Wed, Jun 4
DFW
Dallas-Fort Worth Intl.
HSV
Huntsville Intl.
$253 Roundtrip, found 3 days ago
$253
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Jun 3 from Dallas-Fort Worth Intl. to Huntsville Intl., returning Wed, Jun 4, priced at $253 found 3 days ago
Bargain Flight
Tue, Jun 17 - Tue, Jun 24
CLT
Charlotte-Douglas Intl.
HSV
Huntsville Intl.
$264 Roundtrip, found 12 hours ago
$264
Roundtrip
found 12 hours ago
Select Bargain Flight flight, departing Tue, Jun 17 from Charlotte-Douglas Intl. to Huntsville Intl., returning Tue, Jun 24, priced at $264 found 12 hours ago
Bargain Flight
Tue, May 27 - Sat, May 31
LAX
Los Angeles Intl.
HSV
Huntsville Intl.
$281 Roundtrip, found 4 days ago
$281
Roundtrip
found 4 days ago
Select Bargain Flight flight, departing Tue, May 27 from Los Angeles Intl. to Huntsville Intl., returning Sat, May 31, priced at $281 found 4 days ago
Spirit Airlines
Fri, Aug 8 - Tue, Aug 12
DFW
Dallas-Fort Worth Intl.
CHA
Chattanooga Metropolitan
$356 Roundtrip, found 7 hours ago
$356
Roundtrip
found 7 hours ago
Select Spirit Airlines flight, departing Fri, Aug 8 from Dallas-Fort Worth Intl. to Chattanooga Metropolitan, returning Tue, Aug 12, priced at $356 found 7 hours ago

Cheap Flights to Winchester

Fall in love at first flight with your vacation to Winchester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winchester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winchester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHA airport.

What is the cheapest month to fly to Winchester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winchester are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 13 to choose from for your flight to Winchester.

What airport is best to fly into Winchester?

When you’re planning your trip to Winchester, convenience is the name of the game. Luckily, Winchester Chattanooga Metropolitan Airport is nearby so you can deplane and get going on checking off everything on your Winchester must-do list.

How much are flights to Winchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $86, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winchester?

The trick to saving a stack of cash on your flight to Winchester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $86 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$100

Last Minute Hotel Deals in Winchester

Best Western Inn
Best Western Inn
2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
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! (602 reviews)
"Easy check in and out, CLEAN, good breakfast"

Reviewed on Apr 26, 2025

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Best Western Inn
The Smokehouse Lodge and Cabins
The Smokehouse Lodge and Cabins
3 out of 5
844 W Main Street, Monteagle, TN
Stay at this 3-star hotel in Monteagle. Enjoy free parking, private pools, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,107 reviews)
"We have stayed here several times. It rarely disappoints. It sits on some beautiful property. The rooms are clean. The price is reasonable."

Reviewed on May 21, 2025

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The Smokehouse Lodge and Cabins
Microtel Inn & Suites by Wyndham Manchester
Microtel Inn & Suites by Wyndham Manchester
2 out of 5
201 Expressway Dr, Manchester, TN
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (755 reviews)
"Had no problems at a late night check in. Left too early for the free breakfast so can’t say anything about that although they did let us grab a bit of food there before we left. Price was 95 bucks out the door."

Reviewed on May 22, 2025

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Microtel Inn & Suites by Wyndham Manchester
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
3 out of 5
120 Hospitality Blvd, Manchester, TN
Stay at this 3-star hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.6/10 Excellent! (222 reviews)
"Great stay"

Reviewed on May 18, 2025

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La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
Quality Inn
Quality Inn
2.5 out of 5
509 W Main St, Monteagle, TN
Stay at this hotel in Monteagle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (712 reviews)
Great
"After long drive, got here bout 3-4pm.room was so clean and comfortable. Check in lady was very nice.would definitely recommend this hotel . Keep up good work."

Reviewed on May 20, 2025

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Quality Inn
Holiday Inn Express & Suites Manchester by IHG
Holiday Inn Express & Suites Manchester by IHG
2.5 out of 5
111 Hospitality Blvd, Manchester, TN
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Great Stage Park and May Prairie ...
8.6/10 Excellent! (356 reviews)
"Great delightful place to spend a nice night"

Reviewed on Apr 28, 2025

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Holiday Inn Express & Suites Manchester by IHG
Best Western Shelbyville Inn and Suites Celebration Inn
Best Western Shelbyville Inn and Suites Celebration Inn
2.5 out of 5
724 Madison Street, Shelbyville, TN
Book a stay at this business-friendly hotel in Shelbyville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (544 reviews)
"Bathroom and bed were clean. I was very happy to see that. The staff were very friendly and accommodating., including the kitchen lady. Shampoo and conditioner would like to have them bigger. The bottles were the size of of my thumb :-) Overall, it's a good place to go back!"

Reviewed on May 17, 2025

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Best Western Shelbyville Inn and Suites Celebration Inn
Holiday Inn Express Hotel & Suites Tullahoma by IHG
Holiday Inn Express Hotel & Suites Tullahoma by IHG
2.5 out of 5
2030 N Jackson Street, Tullahoma, TN
Book a stay at this business-friendly hotel in Tullahoma. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (588 reviews)
"Nice hotel"

Reviewed on Apr 30, 2025

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Holiday Inn Express Hotel & Suites Tullahoma by IHG
See all 644 properties in Winchester
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.