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Winchester

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Winchester Flights as Low as $94

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

Frontier Airlines
Mon, Jun 16 - Fri, Jun 20
ORD
O'Hare Intl.
BNA
Nashville Intl.
$94 Roundtrip, found 2 hours ago
$94
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Mon, Jun 16 from O'Hare Intl. to Nashville Intl., returning Fri, Jun 20, priced at $94 found 2 hours ago
Spirit Airlines
Fri, May 30 - Mon, Jun 2
CLT
Charlotte-Douglas Intl.
BNA
Nashville Intl.
$98 Roundtrip, found 9 hours ago
$98
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Fri, May 30 from Charlotte-Douglas Intl. to Nashville Intl., returning Mon, Jun 2, priced at $98 found 9 hours ago
Delta
Wed, May 28 - Wed, May 28
CLT
Charlotte-Douglas Intl.
BNA
Nashville Intl.
$176 Roundtrip, found 9 hours ago
$176
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, May 28 from Charlotte-Douglas Intl. to Nashville Intl., returning Wed, May 28, priced at $176 found 9 hours ago
Spirit Airlines
Mon, May 12 - Fri, May 16
LAS
Harry Reid Intl.
BNA
Nashville Intl.
$176 Roundtrip, found 2 hours ago
$176
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Mon, May 12 from Harry Reid Intl. to Nashville Intl., returning Fri, May 16, priced at $176 found 2 hours ago
American Airlines
Thu, Jun 5 - Tue, Jun 10
ORD
O'Hare Intl.
HSV
Huntsville Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Jun 5 from O'Hare Intl. to Huntsville Intl., returning Tue, Jun 10, priced at $213 found 1 day ago
American Airlines
Tue, Jun 10 - Tue, Jun 17
JAX
Jacksonville Intl.
BNA
Nashville Intl.
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jun 10 from Jacksonville Intl. to Nashville Intl., returning Tue, Jun 17, priced at $220 found 3 days ago
Frontier Airlines
Thu, May 8 - Sun, May 11
MDW
Midway Intl.
BNA
Nashville Intl.
$222 Roundtrip, found 4 days ago
$222
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, May 8 from Midway Intl. to Nashville Intl., returning Sun, May 11, priced at $222 found 4 days ago
Delta
Tue, Jul 1 - Tue, Jul 8
MDW
Midway Intl.
HSV
Huntsville Intl.
$229 Roundtrip, found 4 days ago
$229
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Jul 1 from Midway Intl. to Huntsville Intl., returning Tue, Jul 8, priced at $229 found 4 days ago
American Airlines
Fri, Jul 11 - Tue, Jul 15
SMF
Sacramento Intl.
BNA
Nashville Intl.
$237 Roundtrip, found 3 days ago
$237
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Jul 11 from Sacramento Intl. to Nashville Intl., returning Tue, Jul 15, priced at $237 found 3 days ago
Delta
Tue, May 13 - Tue, May 20
ORD
O'Hare Intl.
CHA
Chattanooga Metropolitan
$257 Roundtrip, found 4 days ago
$257
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, May 13 from O'Hare Intl. to Chattanooga Metropolitan, returning Tue, May 20, priced at $257 found 4 days ago
Bargain Flight
Tue, Jun 17 - Tue, Jun 24
CLT
Charlotte-Douglas Intl.
HSV
Huntsville Intl.
$270 Roundtrip, found 7 hours ago
$270
Roundtrip
found 7 hours ago
Select Bargain Flight flight, departing Tue, Jun 17 from Charlotte-Douglas Intl. to Huntsville Intl., returning Tue, Jun 24, priced at $270 found 7 hours ago
Delta
Tue, May 20 - Sat, May 31
JAX
Jacksonville Intl.
CHA
Chattanooga Metropolitan
$274 Roundtrip, found 5 days ago
$274
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, May 20 from Jacksonville Intl. to Chattanooga Metropolitan, returning Sat, May 31, priced at $274 found 5 days ago
Delta
Mon, Jul 14 - Mon, Jul 21
SMF
Sacramento Intl.
HSV
Huntsville Intl.
$289 Roundtrip, found 2 hours ago
$289
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Jul 14 from Sacramento Intl. to Huntsville Intl., returning Mon, Jul 21, priced at $289 found 2 hours ago
Bargain Flight
Mon, May 5 - Tue, May 6
LAS
Harry Reid Intl.
HSV
Huntsville Intl.
$300 Roundtrip, found 13 hours ago
$300
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Mon, May 5 from Harry Reid Intl. to Huntsville Intl., returning Tue, May 6, priced at $300 found 13 hours ago
American Airlines
Sat, May 10 - Tue, May 13
JAX
Jacksonville Intl.
HSV
Huntsville Intl.
$401 Roundtrip, found 7 hours ago
$401
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Sat, May 10 from Jacksonville Intl. to Huntsville Intl., returning Tue, May 13, priced at $401 found 7 hours ago
American Airlines
Wed, May 7 - Sat, May 10
CLT
Charlotte-Douglas Intl.
CHA
Chattanooga Metropolitan
$454 Roundtrip, found 4 days ago
$454
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, May 7 from Charlotte-Douglas Intl. to Chattanooga Metropolitan, returning Sat, May 10, priced at $454 found 4 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 June, 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 $94, 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 $94 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$91

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 May 8 to May 9
$125
includes taxes & fees
May 8 - May 9
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! (598 reviews)
"Easy check in and out, CLEAN, good breakfast"

Reviewed on Apr 26, 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 May 12 to May 13
$64
includes taxes & fees
May 12 - May 13
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! (1,091 reviews)
"Excellent staff and very clean but outdated room. Room is in dire need to updating,"

Reviewed on Apr 30, 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 May 6 to May 7
$74
includes taxes & fees
May 6 - May 7
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! (728 reviews)
"Excellent"

Reviewed on Apr 27, 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 $134 per night from May 5 to May 6
$134
includes taxes & fees
May 5 - May 6
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! (212 reviews)
"All was good…the staff very friendly and helpful . Check in was efficient. At the coffee bar in the lobby, I missed having a lid for my styrofoam cup to take my coffee with me."

Reviewed on Apr 29, 2025

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
Quality Inn
Quality Inn
2.5 out of 5
509 W Main St, Monteagle, TN
The price is $86 per night from Jun 1 to Jun 2
$86
includes taxes & fees
Jun 1 - Jun 2
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! (703 reviews)
D&V caverns
"Very nice and clean - we were pleasantly surprised with the handiness to everything and the friendliness of the staff."

Reviewed on Apr 28, 2025

Quality 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
The price is $135 per night from May 9 to May 10
$135
includes taxes & fees
May 9 - May 10
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! (355 reviews)
"Great delightful place to spend a nice night"

Reviewed on Apr 28, 2025

Holiday Inn Express & Suites Manchester by IHG
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 $150 per night from May 17 to May 18
$150
includes taxes & fees
May 17 - May 18
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! (585 reviews)
"Nice hotel"

Reviewed on Apr 30, 2025

Holiday Inn Express Hotel & Suites Tullahoma by IHG
Sleep Inn And Suites Manchester
Sleep Inn And Suites Manchester
2.5 out of 5
84 Relco Drive, Manchester, TN
The price is $96 per night from May 28 to May 29
$96
includes taxes & fees
May 28 - May 29
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! (1,002 reviews)
"The room was dated but clean. After 12 hours on the road the bed was quite comfortable"

Reviewed on Apr 30, 2025

Sleep Inn And Suites Manchester
See all 647 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.