Cheap Flight Deals to Winchester TN from CA $148

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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 $145 and CA $148 for one-way flights to Winchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel datesFlights from*
PHLNashvilleDecember 9 to December 17CA $145
SEANashvilleJanuary 23 to January 29CA $219
DFWNashvilleDecember 13 to December 17CA $280
SFONashvilleFebruary 28 to March 4CA $319
ORDNashvilleFebruary 2 to February 6CA $342
LAXNashvilleDecember 8 to December 12CA $452
HOUNashvilleDecember 9 to December 17CA $598
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
SEANashvilleNovember 29 to December 3CA $890
*Prices include taxes and fees

Your guide to flights to Winchester, TN

Flair Airlines, Air Canada fly to Winchester, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Winchester TN currently costs between CA $145 and CA $890. Prices vary, but for the best fares, travel in May 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 $145. 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 January 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

Family Friendly Hotels in Winchester

Best Western Inn

Best Western Inn

2.5 out of 5
1602 Dinah Shore Boulevard, Winchester, TN
The price is CA $130 per night from Dec. 8 to Dec. 9
CA $130
per night
Dec. 8 - Dec. 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 ...
8.8/10 Excellent! (570 reviews)
"Very friendly staff! Easy check in. Very clean rooms."

Reviewed on 13 Nov. 2024

Best Western Inn
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.

Best Winchester Flight and Hotel Packages

Winchester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Bobby Hotel
The Monroe by AvantStay
1 Hotel Nashville
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See all available trips from Toronto to Winchester
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Winchester flight + hotel packages - first class flights

Price found within the past 48 hours. Click for updated prices.
1111 Church
The Harpeth Franklin Downtown, Curio Collection by Hilton
Bobby Hotel
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See all available trips from Toronto to Winchester
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Need a car after flight to Winchester?

Frequently asked questions

Which airlines fly to Winchester?
Being a majortravel hub,it’s not surprising thatWinchesterhas 20airlines that fly in and out of the city.Check out what’s availablewith these popular carriers:

  • Delta Air Lines
  • Southwest Airlines
  • American Airlines

Where to stay in Winchester
A magnificent getaway is just a few clicks away when you book with Travelocity. Select from 101 Winchester accommodations, then start counting down the days until you go!Searching for somewhere to stay in Winchester? The Easy Peasy - Lakefront Home Tim’s Ford Lake Golf Cart Seats 6 and the LAKESIDE at Twin Creeks- 7 minute walk to marina! are our top accommodations in the area.
Places to visit in Winchester
0 But the fun doesn’t need to end there. 0
How to get through airport security fast when traveling to Winchester
These handy tips and pointers about airport security checks will save you plenty of time on your way to Winchester:

  • Ensure your boarding pass and travel ID are easy to reach. You will be asked to present them straightaway.
  • USB sticks, wallets and mobile phones are to be put in a bin for X-raying. If you pass through the body scanner with any one of these items, you’ll be turned around and requested to remove them.
  • Ensure your laptop, phone and other electronic devices are easily accessible. These items need to be sent through the X-ray machine in separate tubs.
  • Toothpaste, lip balm and other toiletry items in gel, liquid or cream form need to be stored in containers smaller than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear zip-lock plastic bag.
  • Think about the type of footwear you want to travel in. Slippers are great because they’re a piece of cake to step out of when you’re doing the airport security checks. Try wearing a pair on your next flight!
  • Pack any pocketknives or other pointy metal items in your checked luggage. Airport security won’t allow these aboard the aircraft.

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.