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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
Sun, Jul 13 - Tue, Jul 15
DTW
Detroit Metropolitan Wayne County
BNA
Nashville Intl.
$80 Roundtrip, found 2 days ago
$80
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sun, Jul 13 from Detroit Metropolitan Wayne County to Nashville Intl., returning Tue, Jul 15, priced at $80 found 2 days ago
Spirit Airlines
Mon, Jul 14 - Fri, Jul 18
ORD
O'Hare Intl.
BNA
Nashville Intl.
$80 Roundtrip, found 2 hours ago
$80
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Nashville Intl., returning Fri, Jul 18, priced at $80 found 2 hours ago
United
Tue, Jul 1 - Thu, Jul 3
EWR
Newark Liberty Intl. Airport
BNA
Nashville Intl.
$109 Roundtrip, found 17 hours ago
$109
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Jul 1 from Newark Liberty Intl. Airport to Nashville Intl., returning Thu, Jul 3, priced at $109 found 17 hours ago
Sun Country Airlines
Sat, Aug 9 - Sat, Aug 16
MSP
Minneapolis - St. Paul Intl.
BNA
Nashville Intl.
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Sun Country Airlines flight, departing Sat, Aug 9 from Minneapolis - St. Paul Intl. to Nashville Intl., returning Sat, Aug 16, priced at $117 found 13 hours ago
JetBlue Airways
Tue, Oct 14 - Wed, Oct 15
BUF
Buffalo Niagara Intl.
BNA
Nashville Intl.
$169 Roundtrip, found 1 hour ago
$169
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Oct 14 from Buffalo Niagara Intl. to Nashville Intl., returning Wed, Oct 15, priced at $169 found 1 hour ago
Spirit Airlines
Mon, Jul 7 - Wed, Jul 9
DTW
Detroit Metropolitan Wayne County
CHA
Chattanooga Metropolitan
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Mon, Jul 7 from Detroit Metropolitan Wayne County to Chattanooga Metropolitan, returning Wed, Jul 9, priced at $190 found 1 hour ago
Frontier Airlines
Thu, Jul 10 - Sat, Jul 12
OMA
Eppley Field
BNA
Nashville Intl.
$204 Roundtrip, found 17 hours ago
$204
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Thu, Jul 10 from Eppley Field to Nashville Intl., returning Sat, Jul 12, priced at $204 found 17 hours ago
American Airlines
Tue, Jun 17 - Mon, Jun 23
EWR
Newark Liberty Intl. Airport
CHA
Chattanooga Metropolitan
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 17 from Newark Liberty Intl. Airport to Chattanooga Metropolitan, returning Mon, Jun 23, priced at $216 found 1 day ago
Bargain Flight
Tue, Oct 14 - Tue, Oct 21
BUF
Buffalo Niagara Intl.
CHA
Chattanooga Metropolitan
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Tue, Oct 14 from Buffalo Niagara Intl. to Chattanooga Metropolitan, returning Tue, Oct 21, priced at $217 found 1 day ago
Bargain Flight
Tue, Jul 1 - Tue, Jul 8
OMA
Eppley Field
HSV
Huntsville Intl.
$219 Roundtrip, found 5 hours ago
$219
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Tue, Jul 1 from Eppley Field to Huntsville Intl., returning Tue, Jul 8, priced at $219 found 5 hours ago
Delta
Sat, Jul 26 - Tue, Jul 29
EWR
Newark Liberty Intl. Airport
HSV
Huntsville Intl.
$253 Roundtrip, found 22 hours ago
$253
Roundtrip
found 22 hours ago
Select Delta flight, departing Sat, Jul 26 from Newark Liberty Intl. Airport to Huntsville Intl., returning Tue, Jul 29, priced at $253 found 22 hours ago
Delta
Wed, Jun 25 - Mon, Jun 30
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$264 Roundtrip, found 2 days ago
$264
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 25 from O'Hare Intl. to Huntsville Intl., returning Mon, Jun 30, priced at $264 found 2 days ago
United
Sat, Oct 18 - Tue, Oct 21
FAT
Fresno Yosemite Intl.
BNA
Nashville Intl.
$286 Roundtrip, found 4 hours ago
$286
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Oct 18 from Fresno Yosemite Intl. to Nashville Intl., returning Tue, Oct 21, priced at $286 found 4 hours ago
American Airlines
Tue, Jun 17 - Mon, Jul 14
OMA
Eppley Field
CHA
Chattanooga Metropolitan
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Jun 17 from Eppley Field to Chattanooga Metropolitan, returning Mon, Jul 14, priced at $297 found 5 days ago
United
Tue, Jun 17 - Wed, Jun 25
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$328 Roundtrip, found 23 hours ago
$328
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Jun 17 from O'Hare Intl. to Chattanooga Metropolitan, returning Wed, Jun 25, priced at $328 found 23 hours ago
American Airlines
Tue, Sep 2 - Sat, Sep 6
DTW
Detroit Metropolitan Wayne County
HSV
Huntsville Intl.
$377 Roundtrip, just found
$377
Roundtrip
just found
Select American Airlines flight, departing Tue, Sep 2 from Detroit Metropolitan Wayne County to Huntsville Intl., returning Sat, Sep 6, priced at $377 just found

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 July, 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 14 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
$80

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! (607 reviews)
"Best Western should have comped or discounted rate as The POOL was not operable due to Maintenance. This should have been disclosed before arrival. Very Disappointed in the communication of an Amenity that was not available. .....Otherwise, Very clean, comfortable and SAFE. Would stay here and recommend ..."

Reviewed on Jun 5, 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! (1,108 reviews)
"It was a nice stay. Restaurant was very good too!"

Reviewed on Jun 15, 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! (784 reviews)
"The staff was very friendly and helpful. We were able to check in early even though it was fully booked."

Reviewed on Jun 12, 2025

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Microtel Inn & Suites by Wyndham Manchester
Sleep Inn And Suites Manchester
Sleep Inn And Suites Manchester
2.5 out of 5
84 Relco Drive, 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 ...
8.8/10 Excellent! (1,001 reviews)
"greatest"

Reviewed on Jun 12, 2025

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Sleep Inn And Suites Manchester
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! (562 reviews)
"Friendly staff and clean rooms"

Reviewed on Jun 15, 2025

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Best Western Shelbyville Inn and Suites Celebration 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! (361 reviews)
"Room was clean and nice"

Reviewed on Jun 12, 2025

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Holiday Inn Express & Suites Manchester by IHG
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! (236 reviews)
"Great place to spend a night, we brought our pet. Everything was fine."

Reviewed on Jun 7, 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! (725 reviews)
"Good basic clean hotel."

Reviewed on Jun 13, 2025

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Quality Inn
See all 651 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.