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Winchester

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Winchester Flights as Low as $80

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

Spirit Airlines
Thu, Oct 23 - Thu, Oct 30
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Detroit Metropolitan Wayne County to Nashville Intl., returning Thu, Oct 30, priced at $80 found 1 day ago
Delta
Sat, Oct 18 - Tue, Oct 21
AUS
Austin-Bergstrom Intl.
BNA
Nashville Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Oct 18 from Austin-Bergstrom Intl. to Nashville Intl., returning Tue, Oct 21, priced at $117 found 6 days ago
Spirit Airlines
Thu, Aug 21 - Sat, Aug 23
RDU
Raleigh - Durham Intl.
BNA
Nashville Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Aug 21 from Raleigh - Durham Intl. to Nashville Intl., returning Sat, Aug 23, priced at $126 found 4 days ago
Spirit Airlines
Thu, Aug 21 - Sun, Aug 24
SAT
San Antonio Intl.
BNA
Nashville Intl.
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Thu, Aug 21 from San Antonio Intl. to Nashville Intl., returning Sun, Aug 24, priced at $132 found 4 days ago
American Airlines
Thu, Aug 28 - Thu, Sep 4
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$161 Roundtrip, found 1 hour ago
$161
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Aug 28 from Detroit Metropolitan Wayne County to Nashville Intl., returning Thu, Sep 4, priced at $161 found 1 hour ago
Delta
Mon, Sep 22 - Fri, Sep 26
RSW
Southwest Florida Intl.
BNA
Nashville Intl.
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Sep 22 from Southwest Florida Intl. to Nashville Intl., returning Fri, Sep 26, priced at $179 found 5 days ago
Frontier Airlines
Sat, Aug 16 - Sat, Aug 23
RDU
Raleigh - Durham Intl.
BNA
Nashville Intl.
$191 Roundtrip, found 4 days ago
$191
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Aug 16 from Raleigh - Durham Intl. to Nashville Intl., returning Sat, Aug 23, priced at $191 found 4 days ago
United
Thu, Aug 28 - Thu, Sep 4
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$193 Roundtrip, found 1 hour ago
$193
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Aug 28 from Detroit Metropolitan Wayne County to Nashville Intl., returning Thu, Sep 4, priced at $193 found 1 hour ago
United
Wed, Nov 12 - Sat, Nov 15
RDU
Raleigh - Durham Intl.
HSV
Huntsville Intl.
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select United flight, departing Wed, Nov 12 from Raleigh - Durham Intl. to Huntsville Intl., returning Sat, Nov 15, priced at $199 found 8 hours ago
Bargain Flight
Sat, Sep 6 - Sat, Sep 13
SAT
San Antonio Intl.
HSV
Huntsville Intl.
$202 Roundtrip, found 9 hours ago
$202
Roundtrip
found 9 hours ago
Select Bargain Flight flight, departing Sat, Sep 6 from San Antonio Intl. to Huntsville Intl., returning Sat, Sep 13, priced at $202 found 9 hours ago
Delta
Thu, Nov 27 - Tue, Dec 2
AUS
Austin-Bergstrom Intl.
HSV
Huntsville Intl.
$217 Roundtrip, found 21 hours ago
$217
Roundtrip
found 21 hours ago
Select Delta flight, departing Thu, Nov 27 from Austin-Bergstrom Intl. to Huntsville Intl., returning Tue, Dec 2, priced at $217 found 21 hours ago
JetBlue Airways
Sun, Sep 21 - Fri, Sep 26
RSW
Southwest Florida Intl.
BNA
Nashville Intl.
$244 Roundtrip, found 5 days ago
$244
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sun, Sep 21 from Southwest Florida Intl. to Nashville Intl., returning Fri, Sep 26, priced at $244 found 5 days ago
Delta
Wed, Sep 17 - Sat, Sep 20
RSW
Southwest Florida Intl.
HSV
Huntsville Intl.
$249 Roundtrip, found 8 hours ago
$249
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Sep 17 from Southwest Florida Intl. to Huntsville Intl., returning Sat, Sep 20, priced at $249 found 8 hours ago
American Airlines
Wed, Oct 8 - Sun, Oct 12
DTW
Detroit Metropolitan Wayne County
CHA
Chattanooga Metropolitan
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Oct 8 from Detroit Metropolitan Wayne County to Chattanooga Metropolitan, returning Sun, Oct 12, priced at $304 found 1 day ago
Delta
Mon, Aug 18 - Mon, Aug 25
PNS
Pensacola Intl.
HSV
Huntsville Intl.
$352 Roundtrip, found 9 hours ago
$352
Roundtrip
found 9 hours ago
Select Delta flight, departing Mon, Aug 18 from Pensacola Intl. to Huntsville Intl., returning Mon, Aug 25, priced at $352 found 9 hours ago
Delta
Thu, Aug 28 - Wed, Sep 10
DTW
Detroit Metropolitan Wayne County
HSV
Huntsville Intl.
$381 Roundtrip, found 6 days ago
$381
Roundtrip
found 6 days ago
Select Delta flight, departing Thu, Aug 28 from Detroit Metropolitan Wayne County to Huntsville Intl., returning Wed, Sep 10, priced at $381 found 6 days 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 October, 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 15 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 $80, 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 $80 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$119

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! (619 reviews)
"Room was clean, staff were very kind and helpful. Property was quiet and well maintained. My only two minor gripes are that the coffee machine was broken both days, and there was what appeared to be mold on the bathroom ceiling. Those were small things, overall I enjoyed my stay."

Reviewed on Jul 25, 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! (1,127 reviews)
"They need to update their website due to the restaurant burning down a year of so.a"

Reviewed on Aug 3, 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! (851 reviews)
"I was a hour away, booked the hotel. When we arrived, it was better than we expected for an awesome rate!!"

Reviewed on Aug 2, 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! (264 reviews)
"Check in person was great and did a wonderful job. Unfortunately the power went out as we were checking in and took awhile for it to come back on."

Reviewed on Aug 2, 2025

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La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
Quality Inn Monteagle

Quality Inn Monteagle

2.5 out of 5
509 W Main St, Pelham, 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 ...
8.6/10 Excellent! (749 reviews)
"Great staff, clean amenities."

Reviewed on Jul 29, 2025

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Quality Inn Monteagle
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! (582 reviews)
"Very comfortable and convenient."

Reviewed on Jul 21, 2025

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Best Western Shelbyville Inn and Suites Celebration Inn
Best Western Kimball Inn

Best Western Kimball Inn

2.5 out of 5
205 Kimball Crossing Dr, Jasper, TN
Stay at this hotel in Jasper. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.2/10 Very Good! (1,002 reviews)
"The room was clean and comfortable. We did notice a really awful smell in the elevator, almost of vomit that they tried to clean but was not very successful. Overall it was a good price and a clean comfortable room for our two night stay."

Reviewed on Aug 3, 2025

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Best Western Kimball Inn
Comfort Suites Manchester near Arnold AFB

Comfort Suites Manchester near Arnold AFB

2.5 out of 5
152 Hospitality Blvd, Manchester, TN
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 ...
9.2/10 Wonderful! (853 reviews)
"Customer service was excellent. Room was clean and fairly quiet. Need a better waffle batter though, the waffles were not good."

Reviewed on Jul 31, 2025

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Comfort Suites Manchester near Arnold AFB
See all 655 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.