$58 Cheap Flights to Winchester, TN

View $58 flight on Tue, Apr 21, 2026Opens in a new window

Popular airlines to Winchester

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Winchester?

Prices were available within the past 7 days and start at $58 for one-way flights and $115 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Apr 21 - Tue, Apr 28
LGA
New York
BNA
Nashville
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Apr 21 from New York to Nashville, returning Tue, Apr 28, priced at $115 just found
Frontier Airlines
Mon, Apr 20 - Thu, Apr 30
PHL
Philadelphia
BNA
Nashville
$118 Roundtrip, found 23 hours ago
$118
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Philadelphia to Nashville, returning Thu, Apr 30, priced at $118 found 23 hours ago
American Airlines
Tue, Jun 30 - Sat, Jul 4
LGA
New York
BNA
Nashville
$137 Roundtrip, just found
$137
Roundtrip
just found
Select American Airlines flight, departing Tue, Jun 30 from New York to Nashville, returning Sat, Jul 4, priced at $137 just found
Spirit Airlines
Wed, Apr 29 - Sat, May 2
PHL
Philadelphia
BNA
Nashville
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Wed, Apr 29 from Philadelphia to Nashville, returning Sat, May 2, priced at $138 found 4 hours ago
Delta
Tue, Apr 28 - Wed, Apr 29
JFK
New York
BNA
Nashville
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Apr 28 from New York to Nashville, returning Wed, Apr 29, priced at $147 found 3 hours ago

Frequently asked questions

What month is the cheapest to fly to Winchester?
April is the cheapest month to travel to Winchester. There's less demand then, so you're likely to score a great deal. Organizing your trip outside of major holidays and school breaks can also help you save.
Which US cities have the cheapest flights to Winchester?
Typically, you'll find that New York, Washington and Orlando offer cheap flights to Winchester. Flexibility, however, is the secret to scoring the lowest fares. Head off during the off-peak season or midweek to keep costs to a minimum.
Which US cities fly direct to Winchester?
Pick from 137 US cities offering direct flights to Winchester. When reserving on Expedia, check "Direct flights only" to compare nonstop options. Fly to Winchester from any of these top cities:

  • New York
  • Washington
  • Orlando
  • Dallas
  • Chicago

How to find a cheap flight to Winchester?
Book early to score cheap flights to Winchester. Also, consider traveling during off-peak months like December and January. If you fly on a Thursday, you can save 16% on average compared to departing on a Sunday.* Save time searching every day and set up a price alert on the Expedia app. We'll notify you when fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Winchester?
Staying flexible with your travel plans might help you to find last-minute offers on cheap flights to Winchester. To view all the available options, try exploring different ticket types, changing your Winchester trip dates, leaving from an alternative airport or using another carrier.
How far in advance should I book a flight to Winchester?
To pick up some of the biggest savings on domestic journeys, book your flight to Winchester 28 days ahead of your travel dates. For international flights, it's between two and four months in advance. This improves your chances of securing the departure dates and seats you want.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Winchester?
You can generally get cheap flights to Winchester on a Sunday. Travelers can save about 8% on average compared to those who book on a Friday, which is typically the most expensive day to book.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Winchester?
A total of 4 airlines connect 13 airports around the world to Winchester. Here are a few of the top airlines to Winchester, where Huntsville Intl. Airport (HSV) is the chief entry point:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • Breeze Airways

Where do you fly into Winchester?
When you're flying to Winchester, the main airport to arrive at is Chattanooga Metropolitan Airport (CHA). You can also jet into nearby hubs like Huntsville Intl. Airport (HSV), Tullahoma, TN (THA-Tullahoma Regional) or Marion County Airport (APT). Another possibility worth keeping in mind when you fly to Winchester is Smyrna Airport (MQY).
How far is the airport from central Winchester?
You'll be roughly 55 mi east of the center of Winchester after arriving at Chattanooga Metropolitan Airport (CHA).
Can I save money by booking a Winchester trip package?
It's possible to save hundreds of dollars if you choose a Winchester flight and hotel package deal on Expedia. And you'll make life easier by having all your travel arrangements in the same place. Try bundling your flight and hotel with add-ons like tours and activities for your own customized Winchester escape.
Can I change or cancel my flight to Winchester?
You can typically cancel or change your flight to Winchester within 24 hours of booking. However, keep in mind that some fares are non-refundable. In those cases, you may be issued a credit toward future travel rather than a direct refund. Be sure to check the airline's rules and restrictions in your itinerary for specific details. Use Expedia's "Changes included" or "No cancel fee" filters when you search to find cheap flights to Winchester with flexible change policies. To learn more, head to our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Nashville Intl.
Destination airport IATA code
BNA
Destination city name
Nashville
Roundtrip price
$115

Trending flights to Winchester

Prices were available within the past 7 days and start at $58 for one-way flights and $115 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Apr 21 - Tue, Apr 28
LGA
New York
BNA
Nashville
$115 Roundtrip, just found
$115
Roundtrip
just found
Select Southwest Airlines flight, departing Tue, Apr 21 from New York to Nashville, returning Tue, Apr 28, priced at $115 just found

Explore a world of travel with Expedia