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Winchester

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Winchester Flights as Low as $58

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

Spirit Airlines
Mon, Apr 28 - Tue, Apr 29
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$58 Roundtrip, found 6 days ago
$58
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Mon, Apr 28 from Detroit Metropolitan Wayne County to Nashville Intl., returning Tue, Apr 29, priced at $58 found 6 days ago
Spirit Airlines
Wed, Apr 30 - Sat, May 3
PHL
Philadelphia Intl.
BNA
Nashville Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Wed, Apr 30 from Philadelphia Intl. to Nashville Intl., returning Sat, May 3, priced at $74 found 1 day ago
Spirit Airlines
Wed, Jun 11 - Wed, Jun 11
MCO
Orlando Intl.
BNA
Nashville Intl.
$106 Roundtrip, found 15 hours ago
$106
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Wed, Jun 11 from Orlando Intl. to Nashville Intl., returning Wed, Jun 11, priced at $106 found 15 hours ago
Delta
Tue, Jul 15 - Sat, Jul 19
LGA
LaGuardia
BNA
Nashville Intl.
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Select Delta flight, departing Tue, Jul 15 from LaGuardia to Nashville Intl., returning Sat, Jul 19, priced at $127 found 11 hours ago
Spirit Airlines
Mon, May 12 - Fri, May 16
LAX
Los Angeles Intl.
BNA
Nashville Intl.
$128 Roundtrip, found 5 days ago
$128
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Mon, May 12 from Los Angeles Intl. to Nashville Intl., returning Fri, May 16, priced at $128 found 5 days ago
Breeze Airways
Fri, May 2 - Sun, May 4
MCO
Orlando Intl.
HSV
Huntsville Intl.
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, May 2 from Orlando Intl. to Huntsville Intl., returning Sun, May 4, priced at $207 found 2 days ago
Frontier Airlines
Sun, Apr 27 - Thu, May 1
SFO
San Francisco Intl.
BNA
Nashville Intl.
$211 Roundtrip, found 1 day ago
$211
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, Apr 27 from San Francisco Intl. to Nashville Intl., returning Thu, May 1, priced at $211 found 1 day ago
American Airlines
Wed, Sep 3 - Wed, Sep 10
DTW
Detroit Metropolitan Wayne County
HSV
Huntsville Intl.
$227 Roundtrip, found 3 days ago
$227
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 3 from Detroit Metropolitan Wayne County to Huntsville Intl., returning Wed, Sep 10, priced at $227 found 3 days ago
Delta
Thu, Jun 5 - Tue, Jun 10
CHS
Charleston Intl.
HSV
Huntsville Intl.
$229 Roundtrip, found 3 days ago
$229
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jun 5 from Charleston Intl. to Huntsville Intl., returning Tue, Jun 10, priced at $229 found 3 days ago
Delta
Sat, May 10 - Wed, May 14
CHS
Charleston Intl.
BNA
Nashville Intl.
$263 Roundtrip, found 17 hours ago
$263
Roundtrip
found 17 hours ago
Select Delta flight, departing Sat, May 10 from Charleston Intl. to Nashville Intl., returning Wed, May 14, priced at $263 found 17 hours ago
Breeze Airways
Fri, May 23 - Mon, May 26
LAX
Los Angeles Intl.
HSV
Huntsville Intl.
$267 Roundtrip, found 6 days ago
$267
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, May 23 from Los Angeles Intl. to Huntsville Intl., returning Mon, May 26, priced at $267 found 6 days ago
Delta
Sat, May 10 - Tue, May 13
SFO
San Francisco Intl.
HSV
Huntsville Intl.
$289 Roundtrip, found 6 days ago
$289
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, May 10 from San Francisco Intl. to Huntsville Intl., returning Tue, May 13, priced at $289 found 6 days ago
Delta
Fri, Jun 6 - Thu, Jun 12
LGA
LaGuardia
CHA
Chattanooga Metropolitan
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, Jun 6 from LaGuardia to Chattanooga Metropolitan, returning Thu, Jun 12, priced at $345 found 1 day ago
Delta
Wed, May 7 - Tue, May 13
PHL
Philadelphia Intl.
HSV
Huntsville Intl.
$356 Roundtrip, found 3 days ago
$356
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, May 7 from Philadelphia Intl. to Huntsville Intl., returning Tue, May 13, priced at $356 found 3 days ago
Delta
Thu, Sep 18 - Sun, Sep 21
DTW
Detroit Metropolitan Wayne County
CHA
Chattanooga Metropolitan
$359 Roundtrip, found 1 hour ago
$359
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, Sep 18 from Detroit Metropolitan Wayne County to Chattanooga Metropolitan, returning Sun, Sep 21, priced at $359 found 1 hour ago
Delta
Tue, Aug 19 - Tue, Aug 19
LAX
Los Angeles Intl.
CHA
Chattanooga Metropolitan
$419 Roundtrip, found 1 day ago
$419
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Aug 19 from Los Angeles Intl. to Chattanooga Metropolitan, returning Tue, Aug 19, priced at $419 found 1 day 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 April, 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 16 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 $58, 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 $58 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$103

Last Minute Hotel Deals in Winchester

Best Western Inn
Best Western Inn
2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
The price is $125 per night from Apr 17 to Apr 18
$125
includes taxes & fees
Apr 17 - Apr 18
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! (596 reviews)
"This was a cute motel in a cute little town. The staff was wonderful, and the room was nice and clean."

Reviewed on Apr 9, 2025

Best Western Inn
The Smokehouse Lodge and Cabins
The Smokehouse Lodge and Cabins
3 out of 5
844 W Main Street, Monteagle, TN
The price is $64 per night from Apr 15 to Apr 16
$64
includes taxes & fees
Apr 15 - Apr 16
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! (1,094 reviews)
Very pleasant hotel
"Very prompt check in at this hotel. It is in a scenic area and room was very clean with comfortable beds. Enjoyed my stay here."

Reviewed on Apr 10, 2025

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
The price is $74 per night from Apr 15 to Apr 16
$74
includes taxes & fees
Apr 15 - Apr 16
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! (705 reviews)
"Nice room okay breakfast good stay would recommend"

Reviewed on Apr 9, 2025

Microtel Inn & Suites by Wyndham Manchester
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
2.5 out of 5
120 Hospitality Blvd, Manchester, TN
The price is $126 per night from Apr 28 to Apr 29
$126
includes taxes & fees
Apr 28 - Apr 29
Stay at this 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! (201 reviews)
"The hotel was clean, but not spotless. The breakfast was barely adequate. The staff was efficient, but not necessarily friendly. I will say the bed and pillows were very comfortable."

Reviewed on Apr 10, 2025

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
Sleep Inn And Suites Manchester
Sleep Inn And Suites Manchester
2.5 out of 5
84 Relco Drive, Manchester, TN
The price is $87 per night from May 14 to May 15
$87
includes taxes & fees
May 14 - May 15
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,001 reviews)
On the road stay
"Clean, comfortable room. Good parking"

Reviewed on Apr 11, 2025

Sleep Inn And Suites Manchester
Quality Inn
Quality Inn
2.5 out of 5
509 W Main St, Monteagle, TN
The price is $101 per night from Apr 21 to Apr 22
$101
includes taxes & fees
Apr 21 - Apr 22
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! (693 reviews)
"Very convenient right off the express way."

Reviewed on Apr 6, 2025

Quality 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
The price is $110 per night from Apr 18 to Apr 19
$110
includes taxes & fees
Apr 18 - Apr 19
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! (582 reviews)
"I would stay again!!"

Reviewed on Mar 30, 2025

Holiday Inn Express Hotel & Suites Tullahoma 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
The price is $121 per night from Apr 14 to Apr 15
$121
includes taxes & fees
Apr 14 - Apr 15
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! (535 reviews)
"Clean and staff was courteous. Only complaint is that it had been really warm that day and could not get the air to cool the room in a reasonable amount of time. Would stay again!"

Reviewed on Apr 7, 2025

Best Western Shelbyville Inn and Suites Celebration Inn
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.