Search Cheap Flights to
Winchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Winchester Flights as Low as $98

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

Breeze Airways
Fri, Jul 17 - Mon, Jul 20
FLL
Fort Lauderdale - Hollywood Intl.
HSV
Huntsville Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jul 17 from Fort Lauderdale - Hollywood Intl. to Huntsville Intl., returning Mon, Jul 20, priced at $98 found 2 days ago
American Airlines
Wed, Aug 26 - Sat, Sep 12
JFK
John F. Kennedy Intl.
BNA
Nashville Intl.
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Wed, Aug 26 from John F. Kennedy Intl. to Nashville Intl., returning Sat, Sep 12, priced at $137 found 1 hour ago
Delta
Wed, Jun 3 - Tue, Jun 9
ATL
Hartsfield-Jackson Atlanta Intl.
BNA
Nashville Intl.
$207 Roundtrip, found 8 hours ago
$207
Roundtrip
found 8 hours ago
Select Delta flight, departing Wed, Jun 3 from Hartsfield-Jackson Atlanta Intl. to Nashville Intl., returning Tue, Jun 9, priced at $207 found 8 hours ago
Delta
Tue, Jun 9 - Tue, Jun 16
FLL
Fort Lauderdale - Hollywood Intl.
CHA
Chattanooga Metropolitan
$230 Roundtrip, found 2 days ago
$230
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 9 from Fort Lauderdale - Hollywood Intl. to Chattanooga Metropolitan, returning Tue, Jun 16, priced at $230 found 2 days ago
JetBlue Airways
Tue, Jul 28 - Tue, Aug 4
RDU
Raleigh - Durham Intl.
BNA
Nashville Intl.
$247 Roundtrip, found 2 days ago
$247
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Jul 28 from Raleigh - Durham Intl. to Nashville Intl., returning Tue, Aug 4, priced at $247 found 2 days ago
Delta
Tue, Jun 16 - Tue, Jun 23
FLL
Fort Lauderdale - Hollywood Intl.
BNA
Nashville Intl.
$257 Roundtrip, found 16 hours ago
$257
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Jun 16 from Fort Lauderdale - Hollywood Intl. to Nashville Intl., returning Tue, Jun 23, priced at $257 found 16 hours ago
American Airlines
Wed, Jun 24 - Wed, Jul 1
JFK
John F. Kennedy Intl.
CHA
Chattanooga Metropolitan
$299 Roundtrip, found 16 hours ago
$299
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Jun 24 from John F. Kennedy Intl. to Chattanooga Metropolitan, returning Wed, Jul 1, priced at $299 found 16 hours ago
Delta
Tue, Jul 21 - Tue, Aug 4
DAL
Love Field
BNA
Nashville Intl.
$299 Roundtrip, just found
$299
Roundtrip
just found
Select Delta flight, departing Tue, Jul 21 from Love Field to Nashville Intl., returning Tue, Aug 4, priced at $299 just found
Delta
Thu, May 28 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
CHA
Chattanooga Metropolitan
$329 Roundtrip, found 2 days ago
$329
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, May 28 from Hartsfield-Jackson Atlanta Intl. to Chattanooga Metropolitan, returning Wed, Jun 3, priced at $329 found 2 days ago
Delta
Thu, May 21 - Thu, May 28
ATL
Hartsfield-Jackson Atlanta Intl.
HSV
Huntsville Intl.
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, May 21 from Hartsfield-Jackson Atlanta Intl. to Huntsville Intl., returning Thu, May 28, priced at $334 found 4 days ago
Delta
Sat, May 23 - Sun, May 24
RDU
Raleigh - Durham Intl.
HSV
Huntsville Intl.
$341 Roundtrip, found 4 days ago
$341
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, May 23 from Raleigh - Durham Intl. to Huntsville Intl., returning Sun, May 24, priced at $341 found 4 days ago
Delta
Tue, Jul 14 - Tue, Jul 28
RDU
Raleigh - Durham Intl.
CHA
Chattanooga Metropolitan
$347 Roundtrip, found 1 day ago
$347
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 14 from Raleigh - Durham Intl. to Chattanooga Metropolitan, returning Tue, Jul 28, priced at $347 found 1 day ago
United
Sun, May 17 - Thu, May 28
XNA
Northwest Arkansas Regional
BNA
Nashville Intl.
$347 Roundtrip, found 2 days ago
$347
Roundtrip
found 2 days ago
Select United flight, departing Sun, May 17 from Northwest Arkansas Regional to Nashville Intl., returning Thu, May 28, priced at $347 found 2 days ago
Delta
Wed, Jun 10 - Tue, Jun 23
DAL
Love Field
CHA
Chattanooga Metropolitan
$469 Roundtrip, found 1 day ago
$469
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Jun 10 from Love Field to Chattanooga Metropolitan, returning Tue, Jun 23, priced at $469 found 1 day ago
United
Thu, May 14 - Sat, May 16
XNA
Northwest Arkansas Regional
CHA
Chattanooga Metropolitan
$498 Roundtrip, found 13 hours ago
$498
Roundtrip
found 13 hours ago
Select United flight, departing Thu, May 14 from Northwest Arkansas Regional to Chattanooga Metropolitan, returning Sat, May 16, priced at $498 found 13 hours ago
Delta
Thu, Jun 11 - Mon, Jun 22
DAL
Love Field
HSV
Huntsville Intl.
$557 Roundtrip, found 5 days ago
$557
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Jun 11 from Love Field to Huntsville Intl., returning Mon, Jun 22, priced at $557 found 5 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 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 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 $98, 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 $98 right now, why wait?

Winchester Flight Information
Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Roundtrip price
$116

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 ...
8.8/10 Excellent! (703 reviews)
Yes

Reviewed on May 11, 2026

Get rates
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 hotel in Monteagle. Enjoy free parking, private pools, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
8.6/10 Excellent! (1,189 reviews)
all good.

Reviewed on May 10, 2026

Get rates
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 ...
8.8/10 Excellent! (1,107 reviews)
Very clean rooms and lobby. Comfortable beds! Staff all very friendly. Nicely updated. The only criticism I will offer is that whatever they use to clean/deodorize the place, the smell is overpowering. I like a fresh, clean smell, but this smelled like someone dumped a whole container of carpet freshener ...

Reviewed on May 10, 2026

Get rates
Microtel Inn & Suites by Wyndham Manchester
The Sewanee Inn

The Sewanee Inn

4 out of 5
1235 University Ave Sewanee TN
Book a stay at this 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! (417 reviews)
The Inn was clean, the staff was polite, the room was larger than expected, the beds were very comfortable and it was SO quite. Got a great nights sleep!

Reviewed on May 8, 2026

Get rates
The Sewanee Inn
Spark by Hilton Kimball

Spark by Hilton Kimball

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 ...
8.4/10 Very Good! (1,004 reviews)
The hotel is only two levels, well located at the entrance of a mall with restaurants, fast foods and covenient stores around it. The parking is tricky with tight spaces. Rooms are the right size with standard essentials. Air conditioner, on the unit I stayed, was working to perfection, the bed super ...

Reviewed on May 9, 2026

Get rates
Spark by Hilton Kimball
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 hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (411 reviews)
Friendly and professional staff, clean and updated interior. The location is great for travelers with a coffee shop, gas stations and restaurants nearby.

Reviewed on May 10, 2026

Get rates
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
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
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! (667 reviews)
Having stayed there when it was new, can say with certainty that it’s outside has deteriorated. But the inside seemed in very good condition, room was nice, clean, and comfortable with lots of thought in design and amenities. Enjoyed the stay overall, once I got past first impressions.

Reviewed on May 10, 2026

Get rates
Holiday Inn Express Hotel & Suites Tullahoma by IHG
Quality Inn Monteagle

Quality Inn Monteagle

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! (871 reviews)
Room was clean, bed a little too firm but pillows were good.

Reviewed on May 5, 2026

Get rates
Quality Inn Monteagle
See all 734 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.