Cheap Flights to Winchester , KY from CA $136

View CA $136 flight on Sat, Aug. 30, 2025Opens in a new window

Popular airlines to Winchester

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

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

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

How much is the cheapest flight to Winchester?

Prices were available within the past 7 days and start at CA $136 for one-way flights and CA $274 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Aug. 18 - Sat, Aug. 30
DTW
Detroit
LEX
Lexington
CA $274 Roundtrip, found 17 hours ago
CA $274
Roundtrip
found 17 hours ago
Select Delta flight, departing Mon, Aug. 18 from Detroit to Lexington, returning Sat, Aug. 30, priced at CA $274 found 17 hours ago
American Airlines
Thu, Aug. 21 - Sun, Aug. 24
DTW
Detroit
LEX
Lexington
CA $300 Roundtrip, found 19 hours ago
CA $300
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Thu, Aug. 21 from Detroit to Lexington, returning Sun, Aug. 24, priced at CA $300 found 19 hours ago
United
Wed, Aug. 13 - Sat, Aug. 16
BUF
Buffalo
LEX
Lexington
CA $396 Roundtrip, found 12 hours ago
CA $396
Roundtrip
found 12 hours ago
Select United flight, departing Wed, Aug. 13 from Buffalo to Lexington, returning Sat, Aug. 16, priced at CA $396 found 12 hours ago
Alaska Airlines
Sat, Nov. 1 - Sat, Nov. 22
SEA
Seattle
LEX
Lexington
CA $582 Roundtrip, found 8 hours ago
CA $582
Roundtrip
found 8 hours ago
Select Alaska Airlines flight, departing Sat, Nov. 1 from Seattle to Lexington, returning Sat, Nov. 22, priced at CA $582 found 8 hours ago
WestJet
Wed, Aug. 6 - Fri, Aug. 15
YEG
Edmonton
LEX
Lexington
CA $587 Roundtrip, found 2 days ago
CA $587
Roundtrip
found 2 days ago
Select WestJet flight, departing Wed, Aug. 6 from Edmonton to Lexington, returning Fri, Aug. 15, priced at CA $587 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?
Winchester is served by just one airport, Blue Grass Airport (LEX).
How far is Blue Grass Airport (LEX) from central Winchester?
The trip from Blue Grass Airport to downtown Winchester is reasonably long. You'll have to travel 40 kilometres before you can check in to your city hotel.
What airport is best to fly into Winchester?
Situated 40 kilometres from the centre of town, Blue Grass Airport (LEX) will likely be your first stop in Winchester.
How many airlines fly to Winchester?
You'll discover 3 airlines that service the route to Winchester. These jet in from 14 airports around the world.
Which airlines fly to Winchester?
Delta operates most of the flights to Winchester. Grabbing a Delta flight from Atlanta is the preferred way of getting there.
How many nonstop flights are there to Winchester?
Flying to someplace new is much more straightforward when there aren't any stopovers to worry about. If you're travelling to Winchester, the good news is that there are 177 nonstop flights operating each week.
Where are the most popular flights to Winchester departing from?
Flights to Winchester from Atlanta, Charlotte and Chicago airports are highly sought after.
How long is the flight to Winchester Airport?
If it's Atlanta you're leaving behind, you'll be in the air for around 1 hour and 14 minutes before you touchdown in Winchester. Terminal to terminal from Charlotte generally takes 1 hour and 29 minutes and from Chicago, the flight time is 1 hour and 29 minutes.
How to book the cheapest flight to Winchester?
Don't leave booking your flight to Winchester until the last moment. That's one move seasoned travellers use to get the best deals. Booking in advance means more options and cheaper flights. Don't stop there, though. Do some research and find out if there are a couple of airports at your destination. Ticket prices often differ depending on which airport you use. Don't forget to compare fares across air carriers as well. Last of all, another easy way to save a few dollars is be ready to book fast. If you spot a fantastic bargain, don't hold off — snap it up while you can.
Do you have any tips for my flight to Winchester?
Depending on where you're coming from, your journey to Winchester could be as easy as pie or it could go on forever. Below are some tips that will help you start your next big adventure on the right foot. What to pack in your hand luggage:

  • The secret to having an amazing travel experience is to pack ahead. First up, the essentials: passport, travel docs, bank cards and vital medications. Next, bring items that'll help pass the time, like some electronic devices or a juicy novel. It's also a wise idea to pack your chargers, a neck pillow and a pair of headphones. Last but not least, be sure to toss in toiletries like a toothbrush, deodorant and a spare change of clothes.

Do not pack the following items in your hand luggage:

  • Squeeze all your full-sized bottles of shampoo and hairspray in your checked baggage. Any liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated by authorities. Sharp or pointed objects, like your Swiss Army knife, and products which are explosive or flammable, such as aerosol cans, spray paint and strong acids, are also restricted.

What to wear on a flight:

  • Your aim is to feel as comfortable as you can. Go for a pair of flat, closed-toe shoes, dress in loose, breathable clothing and remember to bring a pullover in case it gets chilly in the cabin.
  • Deep vein thrombosis (DVT) can pose a risk on long-distance flights. It's the result of blood clots forming due to inactivity and poor circulation, so do some gentle leg and foot exercises in your seat and consider wearing compression socks.

How to get through airport security fast when flying to Winchester?
It's easy — be prepared. We've rounded up some helpful hints for a stress-free trip through security. Watch out Winchester, here you come:

  • Security personnel first need to see that you have a valid ID and travel documents before you can proceed any further. Have them close by, ready for inspection.
  • Next up is the X-ray machine. Empty your pockets and remove anything metal that is likely to set off the scanner's alarm. This includes items like headphones or earphones, as well as your coat or jacket. They'll all need to go on the X-ray conveyor belt.
  • All your electronic gadgets, including your laptop and phone, will also need to be scanned separately.
  • Remember to remove liquids and gels from your carry-on luggage. They often need to be sent through the X-ray machine separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a quart-size (one litre), clear zip-close bag.
  • Choosing your footwear wisely can save you several precious minutes. Boots and heavy shoes are often required to be removed and separately scanned. Lightweight sneakers usually aren't.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, put them in your checked baggage. They won't be allowed on board and will be confiscated.

Flights to Winchester information
Destination airport
Blue Grass
Destination airport IATA code
LEX
Destination city name
Lexington
Roundtrip price
CA $273

Trending flights to Winchester

Prices were available within the past 7 days and start at CA $136 for one-way flights and CA $274 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Thu, Aug. 28 - Tue, Sep. 2
YUL
Montreal
LEX
Lexington
CA $537 Roundtrip, found 5 days ago
CA $537
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Aug. 28 from Montreal to Lexington, returning Tue, Sep. 2, priced at CA $537 found 5 days ago
*Available to Expedia members.