Cheap Flight Deals to Winchester KY from CA $237

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How to find cheap flights to Winchester?

The cheapest prices found with in the last 7 days for return flights were CA $344 and CA $237 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

Your guide to flights to Winchester, KY

United, American Airlines, WestJet fly to Winchester, so use Travelocity to search, find, and compare some truly tempting deals from the 3 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winchester KY currently costs between CA $344 and CA $499. Prices vary, but for the best fares, travel in February when prices are at their lowest.  

Top tips for finding cheap flights to Winchester  

The cheapest flight for a round trip to Winchester is currently CA $344. When you search for flights to Winchester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Winchester for nearby days.  The cheapest month to travel to Winchester is February from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Winchester 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Winchester with Travelocity 

We have top deals on plane tickets even for last minute flights to Winchester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Winchester for less. 

Find The Perfect Hotel For After Your Flight

Amazing Place to Stay After Flight to Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
The price is CA $97 per night from Jan. 25 to Jan. 26
CA $97
CA $107 total
includes taxes & fees
25 Jan - 26 Jan
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.8/10 (639 reviews)
"Staff was very friendly and accommodating"

Reviewed on 29 Dec. 2024

Baymont by Wyndham Winchester
Red Roof Winchester - Lexington East

Red Roof Winchester - Lexington East

2 out of 5
1100 Interstate Drive, Winchester, KY
The price is CA $81 per night from Jan. 28 to Jan. 29
CA $81
CA $90 total
includes taxes & fees
28 Jan - 29 Jan
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lykins Park and Bluegrass Heritage Museum are ...
6.4/10 (530 reviews)
"good"

Reviewed on 9 Jan. 2025

Red Roof Winchester - Lexington East
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is CA $115 per night from Jan. 26 to Jan. 27
CA $115
CA $127 total
includes taxes & fees
26 Jan - 27 Jan
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (890 reviews)
"It was during a snow/ice storm. Staff was nice, easy check in."

Reviewed on 11 Jan. 2025

Best Western Winchester Hotel
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.

Luxury Hotels in Winchester

Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is CA $115 per night from Jan. 26 to Jan. 27
CA $115
CA $127 total
includes taxes & fees
26 Jan - 27 Jan
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (890 reviews)
"It was during a snow/ice storm. Staff was nice, easy check in."

Reviewed on 11 Jan. 2025

Best Western Winchester Hotel
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.

Family Friendly Hotels in Winchester

Baymont by Wyndham Winchester

Baymont by Wyndham Winchester

2.5 out of 5
960 Interstate Dr, Winchester, KY
The price is CA $97 per night from Jan. 25 to Jan. 26
CA $97
CA $107 total
includes taxes & fees
25 Jan - 26 Jan
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.8/10 (639 reviews)
"Staff was very friendly and accommodating"

Reviewed on 29 Dec. 2024

Baymont by Wyndham Winchester
Hampton Inn Winchester

Hampton Inn Winchester

2.5 out of 5
1025 Early Dr, Winchester, KY
The price is CA $158 per night from Feb. 16 to Feb. 17
CA $158
CA $174 total
includes taxes & fees
16 Feb - 17 Feb
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (410 reviews)
"Close to town."

Reviewed on 12 Jan. 2025

Hampton Inn Winchester
Best Western Winchester Hotel

Best Western Winchester Hotel

2.5 out of 5
1307 W Lexington Ave, Winchester, KY
The price is CA $115 per night from Jan. 26 to Jan. 27
CA $115
CA $127 total
includes taxes & fees
26 Jan - 27 Jan
Book a stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (890 reviews)
"It was during a snow/ice storm. Staff was nice, easy check in."

Reviewed on 11 Jan. 2025

Best Western Winchester Hotel
Save an average of 15% on thousands of hotels when you're signed in
Red Roof Winchester - Lexington East

Red Roof Winchester - Lexington East

2 out of 5
1100 Interstate Drive, Winchester, KY
The price is CA $81 per night from Jan. 28 to Jan. 29
CA $81
CA $90 total
includes taxes & fees
28 Jan - 29 Jan
Stay at this hotel in Winchester. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Lykins Park and Bluegrass Heritage Museum are ...
6.4/10 (530 reviews)
"good"

Reviewed on 9 Jan. 2025

Red Roof Winchester - Lexington East
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.

Need a car after flight to Winchester?

Frequently asked questions

Which airlines fly to Winchester?
All set to make some new memories in Winchester? Delta Air Lines is one of the top carriers that service this destination.
What airport is best to fly into Winchester?
Traveling to and from Winchester is effortless, as it’s serviced by just one airport. You’ll find Blue Grass Airport around 40 kilometers from the city center.
Where to stay in Winchester
It’s time to stretch your wings and be inspired by Winchester, and the best place to start is with the search for a place to stay. Travelocity has 13 quality options just waiting to be booked.On the hunt for someplace to stay in Winchester? The 2nd Story Historic Downtown 2BR with Modern Amenities and the Hampton Inn Winchester are our recommended properties in this area.
Places to visit in Winchester
0 Seeking more ideas? 0
How to get through airport security fast when traveling to Winchester
Your trip to Winchester begins as soon as you’ve completed all the security checks. Here is a list of tips and pointers to ensure you get through quickly:

  • Airport security staff will request to see your boarding pass and travel ID at the checkpoint. Keep them in a convenient place, so they’re ready for inspection.
  • It’s useful to know that metal belt buckles can set off the body scanner’s alarms. If you have one on, you may be told to step back and remove it before moving on.
  • Electronics such as laptops, cameras and phones need to be put through the X-ray machine separately. Be sure to have them within easy reach.
  • When you approach the security checkpoint, you’ll be asked to place all creams, gels and liquids in a separate tray for inspection. Make sure they’re all in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Airport security staff will likely tell you to take off your shoes prior to entering the body scanner. Choose a pair that you can slip off easily. There’s nothing more annoying than having to do your laces up again and again.
  • Stash any multi-tools or other sharp items in your checked luggage. Security won’t allow these in carry-on baggage.

Plane Tickets To Winchester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Winchester. Browse through our inventory to explore a wide range of cheap flights to Winchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Winchester as you anxiously await to exit the plane and explore what Winchester has to offer. Considering all the amazing local food and culture in Winchester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Winchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Winchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Winchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Winchester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.