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Winchester

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Winchester Flights as Low as $68

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

Spirit Airlines
Wed, Apr 2 - Sat, Apr 5
BOS
Logan Intl.
BNA
Nashville Intl.
$68 Roundtrip, found 2 days ago
$68
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 2 from Logan Intl. to Nashville Intl., returning Sat, Apr 5, priced at $68 found 2 days ago
Spirit Airlines
Mon, Jun 9 - Fri, Jun 13
IAH
George Bush Intercontinental
BNA
Nashville Intl.
$96 Roundtrip, found 4 days ago
$96
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Mon, Jun 9 from George Bush Intercontinental to Nashville Intl., returning Fri, Jun 13, priced at $96 found 4 days ago
Spirit Airlines
Mon, May 19 - Fri, May 30
LAX
Los Angeles Intl.
BNA
Nashville Intl.
$138 Roundtrip, found 21 hours ago
$138
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Mon, May 19 from Los Angeles Intl. to Nashville Intl., returning Fri, May 30, priced at $138 found 21 hours ago
Frontier Airlines
Mon, Apr 7 - Wed, Apr 16
ONT
Los Angeles - Ontario Intl.
BNA
Nashville Intl.
$151 Roundtrip, found 6 days ago
$151
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Mon, Apr 7 from Los Angeles - Ontario Intl. to Nashville Intl., returning Wed, Apr 16, priced at $151 found 6 days ago
United
Tue, Apr 8 - Wed, Apr 9
MKE
General Mitchell Intl.
BNA
Nashville Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select United flight, departing Tue, Apr 8 from General Mitchell Intl. to Nashville Intl., returning Wed, Apr 9, priced at $157 found 1 day ago
Frontier Airlines
Tue, May 13 - Tue, May 20
SFO
San Francisco Intl.
BNA
Nashville Intl.
$176 Roundtrip, found 6 days ago
$176
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, May 13 from San Francisco Intl. to Nashville Intl., returning Tue, May 20, priced at $176 found 6 days ago
American Airlines
Tue, Jun 17 - Sat, Jun 21
MKE
General Mitchell Intl.
CHA
Chattanooga Metropolitan
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 17 from General Mitchell Intl. to Chattanooga Metropolitan, returning Sat, Jun 21, priced at $217 found 1 day ago
Delta
Mon, Apr 14 - Tue, Apr 15
BOS
Logan Intl.
CHA
Chattanooga Metropolitan
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Apr 14 from Logan Intl. to Chattanooga Metropolitan, returning Tue, Apr 15, priced at $238 found 1 day ago
Delta
Fri, May 9 - Mon, May 12
CLE
Hopkins Intl.
HSV
Huntsville Intl.
$249 Roundtrip, found 14 hours ago
$249
Roundtrip
found 14 hours ago
Select Delta flight, departing Fri, May 9 from Hopkins Intl. to Huntsville Intl., returning Mon, May 12, priced at $249 found 14 hours ago
Delta
Sat, Apr 5 - Tue, Apr 8
MKE
General Mitchell Intl.
HSV
Huntsville Intl.
$254 Roundtrip, found 1 day ago
$254
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Apr 5 from General Mitchell Intl. to Huntsville Intl., returning Tue, Apr 8, priced at $254 found 1 day ago
American Airlines
Sat, Apr 19 - Tue, Apr 22
ONT
Los Angeles - Ontario Intl.
HSV
Huntsville Intl.
$259 Roundtrip, found 2 days ago
$259
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Apr 19 from Los Angeles - Ontario Intl. to Huntsville Intl., returning Tue, Apr 22, priced at $259 found 2 days ago
Delta
Wed, Aug 6 - Wed, Aug 13
SFO
San Francisco Intl.
CHA
Chattanooga Metropolitan
$277 Roundtrip, found 15 hours ago
$277
Roundtrip
found 15 hours ago
Select Delta flight, departing Wed, Aug 6 from San Francisco Intl. to Chattanooga Metropolitan, returning Wed, Aug 13, priced at $277 found 15 hours ago
Delta
Fri, May 9 - Sat, May 17
SFO
San Francisco Intl.
HSV
Huntsville Intl.
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Delta flight, departing Fri, May 9 from San Francisco Intl. to Huntsville Intl., returning Sat, May 17, priced at $289 found 1 day ago
Delta
Mon, May 26 - Sat, Jun 7
ONT
Los Angeles - Ontario Intl.
CHA
Chattanooga Metropolitan
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, May 26 from Los Angeles - Ontario Intl. to Chattanooga Metropolitan, returning Sat, Jun 7, priced at $289 found 1 day ago
United
Thu, Aug 7 - Sun, Aug 10
BOS
Logan Intl.
HSV
Huntsville Intl.
$299 Roundtrip, found 13 hours ago
$299
Roundtrip
found 13 hours ago
Select United flight, departing Thu, Aug 7 from Logan Intl. to Huntsville Intl., returning Sun, Aug 10, priced at $299 found 13 hours ago
United
Wed, Mar 26 - Mon, Mar 31
IAH
George Bush Intercontinental
HSV
Huntsville Intl.
$317 Roundtrip, found 18 hours ago
$317
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Mar 26 from George Bush Intercontinental to Huntsville Intl., returning Mon, Mar 31, priced at $317 found 18 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 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 $68, 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 $68 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$44

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 $116 per night from Mar 24 to Mar 25
$116
includes taxes & fees
Mar 24 - Mar 25
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! (587 reviews)
"The staff was very friendly, and the rooms were very clean. There's a Mexican bar across the street that has amazing food and live bands on Friday night. Please fix your waffle Maker before I come back in a couple months."

Reviewed on Feb 17, 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 Mar 19 to Mar 20
$64
includes taxes & fees
Mar 19 - Mar 20
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! (1,089 reviews)
"Older property but clean and good location."

Reviewed on Mar 16, 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 Mar 20 to Mar 21
$74
includes taxes & fees
Mar 20 - Mar 21
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 ...
8.4/10 Very Good! (646 reviews)
Clean and comfortable
"Clean, spacious, and comfortable stay. Great for quick stay."

Reviewed on Mar 16, 2025

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
The price is $114 per night from Apr 11 to Apr 12
$114
includes taxes & fees
Apr 11 - Apr 12
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! (1,000 reviews)
Nice Hotel
"We stayed one night at the Sleep Inn. The rooms and hotel were very clean. Everything we needed was supplied. The staff was very friendly. I have zero complaints and would stay again."

Reviewed on Mar 10, 2025

Sleep Inn And Suites Manchester
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! (572 reviews)
"Lisa at the front desk was great. They could use a little help with the coffee machines."

Reviewed on Mar 15, 2025

Holiday Inn Express Hotel & Suites Tullahoma by IHG
Quality Inn
Quality Inn
2.5 out of 5
509 W Main St, Monteagle, TN
The price is $101 per night from Apr 2 to Apr 3
$101
includes taxes & fees
Apr 2 - Apr 3
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! (680 reviews)
"Very convenient, right off the highway."

Reviewed on Mar 15, 2025

Quality Inn
Best Western Kimball Inn
Best Western Kimball Inn
2.5 out of 5
205 Kimball Crossing Dr, Jasper, TN
The price is $93 per night from Apr 13 to Apr 14
$93
includes taxes & fees
Apr 13 - Apr 14
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! (1,003 reviews)
"All was good except bed was not comfortable. Needs replaced"

Reviewed on Feb 9, 2025

Best Western Kimball Inn
The Sewanee Inn
The Sewanee Inn
4 out of 5
1235 University Ave, Sewanee, TN
The price is $266 per night from Mar 23 to Mar 24
$266
includes taxes & fees
Mar 23 - Mar 24
Stay at this 4-star golf hotel in Sewanee. Enjoy free WiFi, a golf course, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9.8/10 Exceptional! (344 reviews)
Wonderful weekend stay
"We had a lovely stay at the Sewanne Inn. The lobby is beautiful and cozy and the staff was welcoming and went out of their way to accommodate us. Its proximity to the university is perfect for exploring the campus and hiking trails.We didn’t golf or tennis but the facilities looked nice. The breakfast ..."

Reviewed on Mar 13, 2025

The Sewanee Inn
See all 631 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.