Cheap Flights to Winchester , KY from CA $231

View CA $231 flight on Thu, May 21, 2026Opens in a new window

Popular airlines to Winchester

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How much is the cheapest flight to Winchester?

Prices were available within the past 7 days and start at CA $231 for one-way flights and CA $411 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Mar 10 - Tue, Mar 31
YOW
Ottawa
LEX
Lexington
CA $411 Roundtrip, found 17 hours ago
CA $411
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Mar 10 from Ottawa to Lexington, returning Tue, Mar 31, priced at CA $411 found 17 hours ago
Delta
Tue, Mar 31 - Tue, Apr 14
PHX
Phoenix
LEX
Lexington
CA $422 Roundtrip, found 1 day ago
CA $422
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 31 from Phoenix to Lexington, returning Tue, Apr 14, priced at CA $422 found 1 day ago
American Airlines
Thu, Mar 26 - Tue, Mar 31
SEA
Seattle
LEX
Lexington
CA $457 Roundtrip, found 1 day ago
CA $457
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Mar 26 from Seattle to Lexington, returning Tue, Mar 31, priced at CA $457 found 1 day ago
Air Canada
Tue, Feb 24 - Tue, Mar 3
YHZ
Halifax
LEX
Lexington
CA $482 Roundtrip, found 18 hours ago
CA $482
Roundtrip
found 18 hours ago
Select Air Canada flight, departing Tue, Feb 24 from Halifax to Lexington, returning Tue, Mar 3, priced at CA $482 found 18 hours ago
WestJet
Thu, Jun 25 - Mon, Jun 29
YHZ
Halifax
LEX
Lexington
CA $527 Roundtrip, found 2 days ago
CA $527
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Jun 25 from Halifax to Lexington, returning Mon, Jun 29, priced at CA $527 found 2 days ago

Expedia.ca gives you the best tools to secure great deals on flights to Winchester. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Winchester. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Winchester.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Winchester flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Winchester.

Looking to save even more? Get additional savings by bundling your Winchester flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Winchester trip!

Frequently asked questions

What is the name of Winchester's airport?
Book a flight to Winchester and you'll be touching down at Blue Grass Airport (LEX).
How far is Blue Grass Airport (LEX) from central Winchester?
Long commutes aren't a big deal if you plan ahead of time. Downtown Winchester is 40 kilometres from Blue Grass Airport (LEX), so it's smart to know how to get to the city before you arrive.
What airport is best to fly into Winchester?
A flight to Winchester means touching down at Blue Grass Airport (LEX). Get off the plane, grab your baggage and you'll be 40 kilometres from the centre of town.
How many airlines fly to Winchester?
You have a few options if you're travelling to Winchester. Select from 3 airlines that service the city from 14 airports around the globe.
Which airlines fly to Winchester?
The majority of flights to Winchester are operated by Delta. The most popular route departs from Atlanta, and Delta flies this route the most frequently.
How many nonstop flights are there to Winchester?
Organizing an amazing Winchester getaway is a cinch when there are 177 direct flights each week to choose from.
Where are the most popular flights to Winchester departing from?
Travellers often depart from Atlanta, Charlotte and Chicago airports when flying to Winchester.
How long is the flight to Winchester Airport?
Which city you depart from determines how long you'll be strapped into your seat. From Atlanta to Winchester, the average flight time is 1 hour and 14 minutes. From Charlotte it usually takes 1 hour and 29 minutes, and from Chicago it's 1 hour and 29 minutes.
How to book the cheapest flight to Winchester?
If you want to have some extra spending money on your Winchester vacation, then listen up! As every seasoned jet-setter will tell you, don't leave booking until the last minute. Fares are often highest close to the departure date. Also, shop around and compare your options. If your destination has more than one airport, you may be able to nab a fantastic price by flying into one a little farther out. And finally, don't forget that the early bird catches the worm. Familiarize yourself with airfare costs and be ready to secure your seat as soon as you see a great bargain. The best deals don't last long.
Do you have any tips for my flight to Winchester?
Depending on where you're coming from, your journey to Winchester could be a breeze or it could go on forever. Below are some useful travel tips that will help you start your unforgettable escape on a positive note. What to pack in your hand luggage:

  • A plane ride can be a great experience if you bring the right gear. First things first, you'll need toiletry items, such as a toothbrush and hairbrush, a spare pair of socks and a good novel. Next, find room in your hand luggage for your laptop, a charger, any medications and perhaps a quality neck pillow as well. Lastly, and most importantly, don't forget to take your passport, travel docs and some money.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of hair gel and hairspray in your checked baggage. Any liquids or gels in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp objects, like a pocket knife, and products which are explosive or flammable, such as aerosol cans, flares and matches, are also prohibited.

What to wear on a flight:

  • Your priority is to feel as comfortable as possible. Opt for shoes that are easy to slip on and off, dress in loose, breathable clothing and remember to bring a sweater in case it gets cold in the cabin.
  • Deep vein thrombosis (DVT), a blood clot condition caused by extended periods of inactivity, can be a risk on long-haul flights. Try to walk around the cabin or do some simple exercises in your seat to improve your circulation.

How to get through airport security fast when flying to Winchester?
The answer is simple — be prepared. We've rounded up some top tips for a fuss-free trip through security. Look out Winchester, here you come:

  • First things first. Your boarding pass and passport will need to be presented to airport security. Keep them someplace accessible so you don't hold up the queue.
  • After that, both you and your hand luggage must be X-rayed. To speed things up, take off anything that might trigger the alarms. Personal belongings such as your jacket, belt and earphones need to go through the machine.
  • For just a few minutes, you'll need to unplug from technology. Your phone, laptop and any other electronics will also need to be sent through the scanner.
  • Travelling with a new perfume or cologne? As long as the volume is no greater than 3.4 ounces (100 millilitres) and it's stored in a clear zip-close bag, you can keep it with you in your carry-on.
  • It's also likely that you'll be asked to remove your shoes for scanning, so wearing slip-on sneakers is always a wise idea.
  • Sharp items such as knives and scissors are not allowed in the cabin. They'll be seized at security, so put them in your checked luggage.

Flights to Winchester information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Destination city name
Lexington
Roundtrip price
CA $410

Trending flights to Winchester

Prices were available within the past 7 days and start at CA $231 for one-way flights and CA $411 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Tue, Mar 10 - Tue, Mar 31
YOW
Ottawa
LEX
Lexington
CA $411 Roundtrip, found 17 hours ago
CA $411
Roundtrip
found 17 hours ago
Select United flight, departing Tue, Mar 10 from Ottawa to Lexington, returning Tue, Mar 31, priced at CA $411 found 17 hours ago
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