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Winchester

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Winchester Flights as Low as $72

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

Frontier Airlines
Mon, Sep 15 - Thu, Sep 18
ORD
O'Hare Intl.
BNA
Nashville Intl.
$72 Roundtrip, found 2 days ago
$72
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 15 from O'Hare Intl. to Nashville Intl., returning Thu, Sep 18, priced at $72 found 2 days ago
Spirit Airlines
Sat, Dec 13 - Tue, Dec 16
MCO
Orlando Intl.
BNA
Nashville Intl.
$80 Roundtrip, found 19 hours ago
$80
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sat, Dec 13 from Orlando Intl. to Nashville Intl., returning Tue, Dec 16, priced at $80 found 19 hours ago
Spirit Airlines
Fri, Sep 12 - Mon, Sep 15
MCO
Orlando Intl.
CHA
Chattanooga Metropolitan
$86 Roundtrip, found 3 days ago
$86
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Sep 12 from Orlando Intl. to Chattanooga Metropolitan, returning Mon, Sep 15, priced at $86 found 3 days ago
Frontier Airlines
Mon, Oct 20 - Mon, Oct 27
DFW
Dallas-Fort Worth Intl.
BNA
Nashville Intl.
$94 Roundtrip, found 2 days ago
$94
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Oct 20 from Dallas-Fort Worth Intl. to Nashville Intl., returning Mon, Oct 27, priced at $94 found 2 days ago
Spirit Airlines
Wed, Nov 5 - Tue, Nov 11
LGA
LaGuardia
BNA
Nashville Intl.
$104 Roundtrip, found 20 hours ago
$104
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Wed, Nov 5 from LaGuardia to Nashville Intl., returning Tue, Nov 11, priced at $104 found 20 hours ago
Spirit Airlines
Sat, Oct 18 - Thu, Oct 23
EWR
Newark Liberty Intl. Airport
BNA
Nashville Intl.
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Sat, Oct 18 from Newark Liberty Intl. Airport to Nashville Intl., returning Thu, Oct 23, priced at $120 found 3 days ago
JetBlue Airways
Tue, Nov 4 - Thu, Nov 6
JFK
John F. Kennedy Intl.
BNA
Nashville Intl.
$127 Roundtrip, found 6 days ago
$127
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Nov 4 from John F. Kennedy Intl. to Nashville Intl., returning Thu, Nov 6, priced at $127 found 6 days ago
Breeze Airways
Fri, Dec 12 - Mon, Jan 5
MCO
Orlando Intl.
HSV
Huntsville Intl.
$156 Roundtrip, found 4 days ago
$156
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Dec 12 from Orlando Intl. to Huntsville Intl., returning Mon, Jan 5, priced at $156 found 4 days ago
Delta
Sat, Oct 18 - Sat, Oct 18
DAL
Love Field
BNA
Nashville Intl.
$191 Roundtrip, found 1 day ago
$191
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 18 from Love Field to Nashville Intl., returning Sat, Oct 18, priced at $191 found 1 day ago
Delta
Sat, Oct 18 - Sat, Oct 25
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Oct 18 from O'Hare Intl. to Chattanooga Metropolitan, returning Sat, Oct 25, priced at $209 found 5 days ago
American Airlines
Thu, Oct 30 - Sun, Nov 2
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$209 Roundtrip, found 17 hours ago
$209
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Thu, Oct 30 from O'Hare Intl. to Huntsville Intl., returning Sun, Nov 2, priced at $209 found 17 hours ago
American Airlines
Thu, Sep 18 - Mon, Sep 22
LGA
LaGuardia
HSV
Huntsville Intl.
$222 Roundtrip, found 4 hours ago
$222
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Sep 18 from LaGuardia to Huntsville Intl., returning Mon, Sep 22, priced at $222 found 4 hours ago
Spirit Airlines
Sat, Aug 9 - Wed, Aug 13
EWR
Newark Liberty Intl. Airport
CHA
Chattanooga Metropolitan
$224 Roundtrip, found 1 day ago
$224
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Aug 9 from Newark Liberty Intl. Airport to Chattanooga Metropolitan, returning Wed, Aug 13, priced at $224 found 1 day ago
Bargain Flight
Tue, Aug 12 - Tue, Aug 19
DFW
Dallas-Fort Worth Intl.
HSV
Huntsville Intl.
$256 Roundtrip, found 3 days ago
$256
Roundtrip
found 3 days ago
Select Bargain Flight flight, departing Tue, Aug 12 from Dallas-Fort Worth Intl. to Huntsville Intl., returning Tue, Aug 19, priced at $256 found 3 days ago
Spirit Airlines
Fri, Aug 8 - Tue, Aug 12
DFW
Dallas-Fort Worth Intl.
CHA
Chattanooga Metropolitan
$278 Roundtrip, found 1 day ago
$278
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Aug 8 from Dallas-Fort Worth Intl. to Chattanooga Metropolitan, returning Tue, Aug 12, priced at $278 found 1 day ago
American Airlines
Thu, Sep 18 - Mon, Sep 22
JFK
John F. Kennedy Intl.
HSV
Huntsville Intl.
$333 Roundtrip, found 4 hours ago
$333
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Sep 18 from John F. Kennedy Intl. to Huntsville Intl., returning Mon, Sep 22, priced at $333 found 4 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 September, 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 $72, 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 $72 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! (618 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! (1,128 reviews)
"Excellent service. Very friendly staff! The bed sheets and towels were damp, as was the chair cushions. Maybe it was due to the heat/humidity, and it’s like that all the time but it caused some discomfort as I had to use an extra blanket that was in the drawer to sit and sleep on top of."

Reviewed on Jul 28, 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! (846 reviews)
"No blackout curtains, lights from the street all night bothering. AC old, rags smelling"

Reviewed on Jul 28, 2025

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Microtel Inn & Suites by Wyndham Manchester
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 ...
8.6/10 Excellent! (746 reviews)
"The staff was very friendly. The room was spacious and very clean. The breakfast had many different selections available."

Reviewed on Jul 25, 2025

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Quality Inn
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! (260 reviews)
"This is a great motel. We have stayed here several times and will continue to make it our place of choice in Manchester, TN. The front desk is always very helpful and friendly, the rooms are comfortable and clean, and the area is nice and quiet. It is very close to the highway but you never hear ..."

Reviewed on Jul 28, 2025

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La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
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! (581 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! (1,010 reviews)
"Cleanliness is number one for me."

Reviewed on Jul 27, 2025

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Best Western Kimball Inn
Clarion Pointe Kimball By Choice Hotels

Clarion Pointe Kimball By Choice Hotels

2.5 out of 5
395 Main Street, South Pittsburg, TN
Book a stay at this business-friendly hotel in South Pittsburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
7.4/10 Good! (527 reviews)
"I stay here often. I like the rooms and the bed is great!!"

Reviewed on Jul 20, 2025

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Clarion Pointe Kimball By Choice Hotels
See all 659 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.