A snow-covered river valley with a bridge and a town.

Cheap Flights to Windsor , VT from CA $299

View CA $299 flight on Fri, Sep 11, 2026Opens in a new window

Popular airlines to Windsor

  • 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 rewards
    Sign in

How much is the cheapest flight to Windsor?

Prices were available within the past 7 days and start at CA $299 for one-way flights and CA $559 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
American Airlines
American Airlines
Delta
JetBlue Airways

Frequently asked questions

What is the name of Windsor's airport?
Lebanon Municipal Airport (LEB) is the most popular airport in Windsor.
How far is Lebanon Airport from central Windsor?
If you're staying in central Windsor, it's a smart idea to work out how you'll get into the city before you touchdown. The downtown area is about 18 kilometres from Lebanon Airport.
What airport is best to fly into Windsor?
A flight to Windsor means jumping off the plane at either LEB or RUT. The first is 18 kilometres away from the city centre. The second sits 48 kilometres away.
How many airlines fly to Windsor?
You won't have any trouble choosing who you'll fly to Windsor with — just a single airline services the route. Book well in advance to make sure you can get flights on your preferred dates.
Which airlines fly to Windsor?
Flights into Windsor are typically operated by Cape Air. The highest number of these flights depart from Boston, with Cape Air servicing this route the most often.
How many nonstop flights are there to Windsor?
Flying to someplace new is much simpler when there aren't any annoying stopovers. If you're jetting off to Windsor, the awesome news is that there are approximately 63 direct flights each week.
Where are the most popular flights to Windsor departing from?
Both Boston and White Plains airports offer a huge number of flights to Windsor.
How long is the flight to Windsor Airport?
From the time the wheels leave the tarmac in Boston, you'll be airborne for approximately 1 hour before you land in Windsor. Jet-setters coming in from White Plains can expect to be on the plane for roughly 1 hour and 26 minutes.
How to book the cheapest flight to Windsor?
If you want to have some extra spending money on your trip to Windsor, listen up! As any seasoned traveller will tell you, avoid booking at the last minute. Fares are usually highest just prior to the departure date. Don't stop there, however. Do some research and find out if there are a couple of airports at your destination. Fares often differ depending on the airport you go for. Remember to compare fares across airlines too. And finally, remember that the early bird catches the worm. Familiarize yourself with airfare costs and have your credit card ready to buy your ticket as soon as you spot an unbeatable bargain. The best deals never last long.
Do you have any tips for my flight to Windsor?
We've rounded up all the info you need to make your journey as stress-free as possible. Follow our tips and you'll be hightailing it through airport security and having a blast in Windsor before you know it. What to pack in your hand luggage:
  • The secret to having a pain-free flight experience is to plan ahead. First up, the essentials: passport, travel documents, cash and any vital medications. Next, take on board items that'll help keep you entertained, like some electronic gadgets or a magazine. You'll also want to bring your chargers, a neck pillow and a pair of headphones. And of course, don't forget to pop in toiletry items like a toothbrush, cleansing wipes and a clean T-shirt.
Do not pack the following items in your hand luggage:
  • Pack all your full-sized bottles of hair gel and hairspray in your checked luggage. Any liquids or gels in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated by security. Sharp or pointed objects, like your beloved pocket knife, and dangerous goods which are explosive or flammable, such as aerosol cans, spray paint and strong acids, are also restricted.
What to wear on a flight:
  • The aisles of a plane are no place for a fashion parade. Layer your clothing and pick shoes that are roomy, flat and easy to take on and off.
  • Caused by sustained periods of immobility, deep vein thrombosis (DVT) is a blood clot condition that can affect some passengers on long-distance flights. Reduce the risks by staying hydrated, keeping your lower limbs moving and wearing compression socks or tights.
How to get through airport security fast when flying to Windsor?
Being prepared before you get to the airport will help make your trip to Windsor a breeze. We've compiled some handy tips and tricks for a swift journey through security:
  • Your passport and travel documents will need to be presented to airport security. Keep them handy to avoid fumbling around for them.
  • Next up is the X-ray machine. Empty your pockets and remove anything that is likely to set off the alarm. This includes items like earphones or headphones, as well as heavy jackets or coats. They'll need to be placed on the conveyor belt for screening.
  • Electronic devices like laptops and phones will also need to go on a tray for inspection. Don't worry, you'll be back online soon enough.
  • Any gels or liquids, such as perfume or hairspray, that you want to bring on board need to be in containers no greater than 3.4 ounces (100 millilitres). Also, they all must fit inside a quart-size (one litre), clear zip-close bag.
  • Slip-on shoes are a practical footwear choice as you're less likely to have to remove them when going through security. Big boots and other bulky shoes are often subjected to extra screening.
  • Sharp items are prohibited in the cabin. They'll be confiscated at security, so pack them safely away in your checked baggage.

Book with confidence

Expedia.ca gives you the best tools to secure great deals on flights to Windsor. 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 Windsor. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Windsor.

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 Windsor 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 Windsor.

Looking to save even more? Get additional savings by bundling your Windsor 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 Windsor trip!

Travel information

Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Destination city name
Lebanon
Roundtrip price
CA $559

Trending flights to Windsor

Prices were available within the past 7 days and start at CA $299 for one-way flights and CA $559 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines

Explore a world of travel with Expedia

*Available to Expedia members.