Cheap Flights to Windsor , VT from CA $338

Featured airlines

Air Canada
Air Transat
WestJet
American Airlines
Flair Airlines
Philippine Airlines
Air India
Lufthansa
Caribbean Airlines

  • 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 Windsor?

Prices were available within the past 7 days and start at CA $119 for one-way flights and CA $260 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
JetBlue Airways
Boston — Rutland
BOS - RUT with JetBlue Airways
Mon, Jan 6
Rutland — Boston
RUT - BOS with Cape Air
Sun, Jan 12
Found 5 hours ago
From CA $260
Select flight from Boston to Rutland, departing on January 6 with JetBlue Airways, and returning from Rutland to Boston on January 12 with Cape Air. Price from CA $260, Found 5 hours ago.
JetBlue Airways
Boston — Rutland
BOS - RUT with JetBlue Airways
Mon, Jan 6
JetBlue Airways
Rutland — Boston
RUT - BOS with JetBlue Airways
Sun, Jan 12
Found 5 hours ago
From CA $263
Select flight from Boston to Rutland, departing on January 6 with JetBlue Airways, and returning from Rutland to Boston on January 12 with JetBlue Airways. Price from CA $263, Found 5 hours ago.
Boston — Rutland
BOS - RUT with Cape Air
Mon, Jan 6
Rutland — Boston
RUT - BOS with Cape Air
Sun, Jan 12
Found 5 hours ago
From CA $264
Select flight from Boston to Rutland, departing on January 6 with Cape Air, and returning from Rutland to Boston on January 12 with Cape Air. Price from CA $264, Found 5 hours ago.
American Airlines
Vancouver — Lebanon
YVR - LEB with American Airlines
Wed, Jan 15
Lebanon — Vancouver
LEB - YVR with Cape Air
Sat, Feb 1
Found 18 hours ago
From CA $510
Select flight from Vancouver to Lebanon, departing on January 15 with American Airlines, and returning from Lebanon to Vancouver on February 1 with Cape Air. Price from CA $510, Found 18 hours ago.
Delta
Calgary — Lebanon
YYC - LEB with Delta
Sun, Feb 2
Lebanon — Calgary
LEB - YYC with Cape Air
Wed, Feb 19
Found 5 days ago
From CA $592
Select flight from Calgary to Lebanon, departing on February 2 with Delta, and returning from Lebanon to Calgary on February 19 with Cape Air. Price from CA $592, Found 5 days ago.

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!

Frequently asked questions

What is the name of Windsor's airport?
Lebanon Municipal Airport (LEB) is the only airport in Windsor.
How far is LEB from central Windsor?
If you plan on staying in central Windsor, it’s a good idea to organize how you’ll get into the city before you touchdown. The downtown area is approximately 18 kilometres from Lebanon Municipal Airport (LEB).
What airport is best to fly into Windsor?
Disembark the plane at Lebanon Airport and you’ll be 18 kilometres from the downtown area. Rutland Southern Vermont Regional Airport (RUT) also welcomes many travelers to Windsor. It’s 40 kilometres from the city center.
How many airlines fly to Windsor?
If you’re flying to Windsor, there isn’t a lot of choice. Just one airline operates on the route — get in fast to pick up the best deal.
Which airlines fly to Windsor?
Flights into Windsor are typically run by Cape Air. The largest proportion of these flights set off from Boston, with Cape Air servicing this route the most.
How many nonstop flights are there to Windsor?
Planning an awesome Windsor getaway is a walk in the park when there are 63 nonstop flights every week to choose from.
Where are the most popular flights to Windsor departing from?
Flights traveling from Boston to Windsor typically get booked out the fastest.
How long is the flight to Windsor Airport?
Strap yourself in and get comfortable. Typically, flights from Boston to Windsor take approximately 1 hour and 4 minutes.
How to book the cheapest flight to Windsor?
We’ve all come across those fortunate travelers who somehow nab incredibly cheap fares wherever they go. Want to know how to do it for your Windsor vacation? Don’t leave it until the last moment to lock in your flight. Also, look around online and compare your options. If your destination has a few airports, you may be able to nab a great price by flying into one a little farther out. And finally, remember that it’s first in, best dressed. Know what a typical airfare costs and have your credit card ready to reserve your seat as soon as you see an unbeatable bargain. The best deals don’t last long.
How to survive the flight to Windsor?
If you’re poorly prepared, air travel can be tough. But there’s no need to hit the panic button just yet. Follow these useful tips and enjoy a pain-free start to your vacation in Windsor.What to pack in your hand luggage:

  • A plane ride can be a comfortable experience if you take the right gear. First of all you’ll need basic toiletry items, such as a toothbrush and lip balm, a fresh change of clothes and a good read. Next, leave space in your hand luggage for your electronic devices, chargers, any daily medications and perhaps a cozy neck pillow as well. Last, but definitely not least, be sure to bring your passport, travel documents and your bank cards.

Do not pack the following items in your hand luggage:

  • Check carefully that you don’t have sharp or pointed objects hiding in one of the zippers of your carry-on luggage. Other banned items include flammable or explosive substances, such as aerosol cans and fuel, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 milliliters).

What to wear on a flight:

  • The answer to a comfortable flight often lies in your choice of clothes. Prepare yourself for varying temperatures by bringing layers. This will keep you nice and warm if the cabin gets chilly. Shoes like stilettos, flip flops and lace-up boots are best left in your checked suitcase. Instead, go for flat, closed-toed footwear like slip-ons. Your feet will thank you later.
  • Most travelers are aware of deep vein thrombosis (DVT), a blood clot condition caused by reduced mobility or inactivity. There’s plenty you can do to lower your risk. Wear a quality pair of compression tights or socks, drink lots of water often and get your legs and feet moving. Walk around the cabin when possible or perform some simple exercises in your seat.

How to get through airport security fast when flying to Windsor?
As savvy travelers know, the secret is to be well organized before you arrive at the airport security gate. That way, you’ll be boarding that plane to Windsor in next to no time. Follow these tips and get your trip off to a fantastic start:

  • Your passport and travel documents will need to be shown to airport security personnel. Keep them at hand so you don’t have to dig around for them.
  • After that, both you and your hand luggage will be X-rayed. To make the process quick and painless, remove anything that might trigger the alarms. Items such as your belt, jacket and headphones need to go through the machine.
  • For just a few minutes, you’ll have to unplug from the digital world. Your phone, tablet and any other electronics will also need to go through the scanner.
  • Remove all gels and liquids from your carry-on luggage. They often need to be sent through the X-ray separately. Each item should be no larger than 3.4 ounces (100 milliliters) and everything must fit inside a single quart-size (one liter), clear zip-lock bag.
  • There’s a chance you’ll need to remove your shoes for scanning, so wearing slip-on shoes is always a wise idea.
  • Airlines will not allow any sharp objects in the cabin. If you must bring these kinds of items, put them in your checked luggage.

Flights to Windsor information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Destination city name
Rutland
Roundtrip price
CA $259

Trending flights to Windsor

Prices were available within the past 7 days and start at CA $342 for one-way flights and CA $510 for roundtrip, for the period specified. Prices and availability are subject to change. Additional terms apply.
*Available to Expedia members.