Cheap Flights to Windsor, VT

Flights to Windsor at a glance

Traveling to Windsor is a breeze—select from a range of full-service or budget-friendly airlines, compare travel times, and choose what best fits your budget and itinerary as you plan to discover the city's renowned attractions and neighborhoods.

• Major airports near Windsor: Rutland Southern Vermont Regional Airport (RUT), Lebanon Municipal Airport (LEB)
• Closest airport to Windsor: Lebanon Municipal Airport, LEB (around 11 miles)
• Flights per week: 39 flights arriving across Windsor airports
• Number of airlines that fly to Windsor: around 4 carriers

Popular airports near Windsor

Windsor is a charming city perfect for outdoor enthusiasts, adventure seekers, and ski vacationers. Travelers flock to Windsor for its skiing, sports, romance, and outdoor activities. The city is conveniently accessible via two major airports, making travel easy and efficient.

• Rutland Southern Vermont Regional Airport (RUT): Situated in Rutland County, Vermont, approximately 28 miles from Windsor, this airport offers domestic flights to around 2 destinations nationwide. Key airlines that operate here include Hahn Air and JetBlue Airways.
• Lebanon Municipal Airport (LEB): Found in Grafton County, New Hampshire, roughly 11 miles from Windsor, this airport provides domestic services to approximately 3 cities across the United States. Notable carriers include Hahn Air, JetBlue Airways, and Delta.

Top routes to Windsor

• Boston (BOS) to Windsor (LEB/RUT), with one-way fares starting at around $65
• Washington (DCA) to Windsor (LEB/RUT), with one-way flight options from around $180
• White Plains (HPN) to Windsor (LEB), with one-way airfare from around $95

Cheapest routes to Windsor

• Boston (BOS) to Windsor (LEB/RUT), with affordable one-way prices from around $65
• White Plains (HPN) to Windsor (LEB), with low one-way fares from around $95
• Washington (DCA) to Windsor (LEB/RUT), with low-cost one-way tickets from around $180

*Flight times and fares vary by season and availability and are based on one-way routes

Top airlines with flights to Windsor

• Hahn Air: This airline operates flights to Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT), representing roughly 57% of all arrivals in Windsor. The typical one-way fare is around $110.
• JetBlue Airways: JetBlue serves Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT), contributing to about 36% of arrivals to Windsor. Average one-way fares are approximately $150.
• Delta: Offering service to Lebanon Municipal Airport (LEB), Delta accounts for nearly 4% of arrivals in Windsor. The average fare for a one-way ticket is about $240.
• American Airlines: American Airlines flies to Lebanon Municipal Airport (LEB), making up around 3% of Windsor's arrivals. The typical one-way fare is approximately $310.

Best time to fly to Windsor

The most popular months for travelers to fly to Windsor are January, March, and April, when peak temperatures in Windsor can reach up to 39.4°F in April. If you prefer quieter travel, consider December, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 24.3°F. For better deals, February usually offers the lowest average one-way fare around $96, roughly 29% cheaper than the yearly average.

*Average one-way fare is based on Expedia flight booking data from January 2025 to April 2026 for the specified route and travel class and may change depending on availability, dates, and demand.

How to save money on a flight to Windsor

Getting some of the best deals on flights to Windsor is all about timing and flexibility. Here are some key tips to help you save:

1. Compare flight options—use Expedia's search tool to compare airlines, routes, direct vs. non-direct flights, and flight times. You can also sort by price to find the most affordable options.
2. Set up price alerts—as an Expedia member you can use Price Tracking to receive notifications when flight prices change.
3. Bundle and save—book a flight and unlock a hotel deal on Expedia.*
4. Think about luggage-nowadays, it's important to check the airline's baggage policies to find the best value. That may be paying for an additional carry-on bag or booking a ticket with checked luggage included. Either way, double-check your baggage allowance before confirming your booking to avoid excess baggage fees at the airport.
5. Earn miles—you can earn airline miles when you book your Windsor flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Windsor

Windsor welcomes travelers through its range of transport options based on price, convenience, and proximity. Here's how to reach Windsor efficiently:

• Public transportation: From Rutland Southern Vermont Regional Airport, Wallingford Bus Station (a bus station) is located about 5.8 miles from the airport by car, while Rutland Station (a train station) is situated approximately 6.8 miles away, also most conveniently reached by car.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Windsor, with private rides that can be arranged in advance.
• Car rental: Renting a car in Windsor is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Windsor on Expedia.
• Taxi/ride-hailing: Taxis and ride-hailing services may be available from designated pickup areas outside the terminal, check locally on arrival.

Where to stay around Windsor

• Cavendish: Located 11 miles away from Windsor, Cavendish is a charming city that serves as a gateway for adventure seekers. Known for its ski resorts and outdoor activities, visitors can enjoy skiing on the slopes or exploring the breathtaking scenery of Mount Ascutney. For a romantic day out, Lake Rescue offers a picturesque setting perfect for beach activities. Nature lovers will appreciate Mt Ascutney State Park, where hiking and enjoying the great outdoors are top priorities.
• Lebanon: Lebanon is located 13 miles away from Windsor and is an exciting destination for those who enjoy outdoor adventures and skiing. The city boasts prominent landmarks such as Dartmouth College, a historic institution that adds a cultural touch to your visit. Outdoor enthusiasts can explore the stunning Quechee Gorge Bridge, offering scenic views and adventure opportunities. Colburn Park is a local landmark that invites visitors to relax and soak in the atmosphere of this vibrant city.
• Cornish: Situated only 1 mile away from Windsor, Cornish is a delightful city known for its outdoor experiences and ski activities. Visitors can explore the artistic offerings at the Saint-Gaudens National Historic Site, which showcases cultural heritage. For adventure seekers, Mount Ascutney provides ample opportunities for hiking and enjoying the natural beauty of the area. The nearby Quechee Gorge Bridge is also a must-see, offering spectacular views and outdoor exploration for those looking to connect with nature.

Tips for short-haul flights to Windsor

For quick getaways, efficiency is key. Here is how to make your short-haul journey smoother:

• Pack light and skip checked bags—when flying with budget airlines, it’s often more economical to travel with just a carry-on. Optimize your packing by including mini toiletries, wearing your bulkiest clothing, and coordinating outfits effectively. This approach also allows you to bypass the wait at baggage claim upon arrival.
• Bring your own entertainment—many short-haul flights may not provide in-flight entertainment options. Download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book to keep yourself engaged. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—even for short or domestic flights, it’s advisable to arrive at least 1.5 to 2 hours prior to your departure, taking into account traffic and security lines.
• Bring your own snacks and water—pack some snacks along with a refillable water bottle to stay hydrated and save money at the airport.

Tips for long-haul flights to Windsor

Flying long-haul sometimes requires extra planning to ensure a comfortable journey:

• Select your seat in advance—for longer flights, choosing your seat is essential for comfort. Full-service airlines often allow you to select a seat for free once online check-in opens, typically 24–48 hours before your flight. Some airlines may offer seat selection even earlier than this.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours before departure for international flights. This will give you ample time for check-in, security, and immigration procedures.
• Relax at the airport—if you find yourself with extra time, take the opportunity to explore the shops, grab a coffee, or unwind at the gate or in a departure lounge if you have access. Most airports provide free Wi-Fi for your convenience.
• Adjust to the new time zone mid-flight—begin the process of syncing your body clock by changing your watch and sleep schedule to align with your destination's time zone. Try to sleep or stay awake during the flight according to the local time of your arrival to help minimize jet lag.

Tips to find the cheapest flights to Windsor

The cheapest day to fly

Get started finding a cheap flight to Windsor on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

The cheapest month to fly

is the cheapest month to fly to Windsor. This coincides with the low season when fewer people travel. Whichever month you travel in, though, be sure to book at least a month in advance if you want to score cheap tickets to Windsor. ARC's data shows that domestic flights booked 28 days or more before departure are typically 24% cheaper than those booked last minute.

The most affordable time to book a flight

Typically, a Sunday can be the cheapest time to book a flight to Windsor, according to ARC’s data. On average, you could save between 6% and 13% by booking on a Sunday instead of a Friday, which is the most expensive day to make a reservation.

The cheapest round-trip tickets to Windsor

The lowest price for round-trip flights to Windsor in 2026 starts from , while one-way tickets start from . Expedia's effective search tool is one of the best ways to find a budget airfare. Simply enter your dates, and within seconds, it'll show you a vast selection of the cheapest flights to Windsor. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Windsor

are just some of the airlines that can typically offer cheap tickets to Windsor. You can find their most affordable flights by using the “airline” search filter and then sorting prices from low to high. As a trusted partner of the world's leading airlines, Expedia offers you some of the best airfare deals to Windsor and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Windsor, simply order your search results from lowest to highest price. Expedia's search tool compares flight prices for all airports close to your destination, so you don't have to manually search them one by one to find the cheapest flight to Windsor. If you have a preferred place to fly into, take advantage of the “arrival airport” filter to narrow down your search on Expedia.

Save with a package

With Expedia's amazing package deals, you could save hundreds of dollars by booking your Windsor plane tickets together with your accommodations, car rental, or activities. Just select the search wizard's “package” option to view some of the cheapest deals. Look out for the green savings label to see how much you're saving.

Date flexibility for the cheapest flights to Windsor

If you can be flexible with your travel dates, it's a good idea to broaden your search by comparing prices on different days. This will open up more options, meaning you could uncover a less expensive flight to Windsor.

Stopover savings

The cheapest tickets to Windsor are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Windsor. While the overall travel time might be longer than a non-stop flight, you may decide it's worth it for the money saved.

Get Expedia's Price Drop Protection

Price Drop Protection means that if your flight gets cheaper after booking, you'll be credited the difference*. This gives you peace of mind that you're getting one of the cheapest flights to Windsor for your chosen departure. Expedia's Price Drop Protection is available for a small fee but is free to One Key Gold and Platinum tier members.

*Terms apply.

Use our Price Tracking feature

Expedia's Price Tracking feature is another great tool that removes the guesswork from finding cheap flights to Windsor. Simply download the free Expedia app to your smart device and activate Windsor flight price alerts for your travel dates. There's even a price predictor tool that uses historical data to indicate the best time to book, giving you peace of mind that you'll nab the lowest prices.

Book with Expedia

As well as Price Drop Protection and Price Tracking, Expedia's close partnership with a vast selection of the world's leading airlines means you're sure to find cheap flights to Windsor. Plus, the One Key rewards program lets you earn real cash rewards on most bookings that you can use to save money on future trips. Best of all, it's free to join, and members often unlock exclusive discounts, too.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.