$90 Cheap Flights to Windham, VT

Flights to Windham at a glance

Traveling to Windham is easy; you can select from full-service or budget airlines. Just compare flight durations and choose the option that best fits your budget, schedule, and plans to visit the city's renowned attractions and neighborhoods.

• Major airports near Windham: Rutland Southern Vermont Regional Airport (RUT), Lebanon Municipal Airport (LEB)
• Closest (typical) airport to Windham: Rutland Southern Vermont Regional Airport, RUT (around 27 miles)
• Flights per week: 39 flights arriving across Windham airports
• Number of airlines that fly to Windham: around 4 carriers

Popular airports near Windham

Windham is a charming village perfect for ski trips and adventure-filled sports vacations. Visitors are drawn to Windham for its outdoor activities, skiing, adventure, sports, and romantic getaways. The village is conveniently accessed via two major airports.

• Rutland Southern Vermont Regional Airport (RUT): Situated in Rutland County, Vermont, approximately 27 miles from Windham, this airport offers domestic flights to around 2 cities nationwide. Key airlines operating here include Hahn Air and JetBlue Airways, providing travelers with various options.
• Lebanon Municipal Airport (LEB): Found in Grafton County, New Hampshire, roughly 38 miles from Windham, this airport connects travelers to about 3 cities within the United States. Major carriers at this location include Hahn Air, JetBlue Airways, and Delta, ensuring a range of flight services.

Top routes to Windham

• Boston (BOS) to Windham (LEB/RUT), with one-way flight options from around $65
• White Plains (HPN) to Windham (LEB), with one-way tickets available from around $95
• Washington (DCA) to Windham (LEB/RUT), with one-way tickets available from around $180

Cheapest routes to Windham

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

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

Top airlines with flights to Windham

• Hahn Air: Operating flights to Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT), Hahn Air represents about 57% of Windham's incoming traffic. On average, a one-way ticket costs around $110.
• JetBlue Airways: Offering services to Lebanon Municipal Airport (LEB) and Rutland Southern Vermont Regional Airport (RUT), JetBlue accounts for roughly 36% of arrivals in Windham, with one-way fares averaging about $150.
• Delta: Providing flights to Lebanon Municipal Airport (LEB), Delta is responsible for about 4% of Windham's arrivals. The typical one-way fare is around $240.
• American Airlines: With flights to Lebanon Municipal Airport (LEB), American Airlines makes up about 3% of arrivals to Windham, and the average one-way fare is approximately $310.

Best time to fly to Windham

The most popular months for travelers to fly to Windham are January, March, and April, when peak temperatures in Windham can reach up to 41.9°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 26.8°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 Windham

Getting some of the best deals on flights to Windham 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*, or explore our Windham hotel and flight deals.
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 Windham flight with Expedia. Just select your frequent flyer program and enter your program number when confirming your booking.

*For members. Select hotels.

Arriving in Windham

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

• Public transportation: From Rutland Southern Vermont Regional Airport, Wallingford Bus Station (a bus station) is located about 5.8 miles away by car, while Rutland Station (a train station) is situated approximately 6.8 miles from the airport, also accessible by car, providing convenient transport options for travelers.
• Hotel transfer: Transfers offer a convenient way to reach your hotel in Windham, with private rides that can be arranged in advance.
• Car rental: Renting a car in Windham is a good option if you plan to explore and sightsee beyond the city. Browse cheap car rentals in Windham 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 Windham

• Grafton: Located 8 miles drive away from Windham, Grafton is a charming city that entices visitors with its outdoor adventures. Ski enthusiasts will appreciate the nearby ski fields and resorts, while nature lovers can explore scenic landmarks like Jamaica State Park, perfect for hiking and relaxation. Don't miss Plummer's Sugar House for a glimpse into local maple syrup production, or the Vermont Museum of Mining and Minerals for a cultural experience that the whole family will enjoy.
• Jamaica: Jamaica is located 10 miles drive away from Windham and is a haven for those seeking thrilling outdoor activities. Known for its excellent skiing opportunities, the city also boasts beautiful natural attractions such as Jamaica State Park, a fantastic spot for adventure and picturesque views. The Ball Mountain Dam offers stunning scenery, while the Winhall River invites visitors to unwind in nature's embrace, making it an ideal destination for outdoor vacations.
• Andover: Andover is located 7 miles away from Windham and offers a peaceful village atmosphere paired with exciting recreational options. This destination is perfect for skiing, with nearby resorts catering to winter sports enthusiasts. Nature lovers can visit Lowell Lake State Park for outdoor adventures and breathtaking scenery. For a unique cultural experience, stop by Weston Priory, a serene monastery that adds to the village's charm. Lake Rescue is also nearby, providing a romantic and scenic spot for relaxation.

Tips for short-haul flights to Windham

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, traveling with just a carry-on is often the more economical choice. Maximize your packing by bringing mini toiletries, wearing your heaviest clothing, and coordinating your outfits. This approach also helps you steer clear of waiting at baggage claim once you arrive.
• Bring your own entertainment—many short-haul flights may lack in-flight entertainment options. To keep yourself occupied, download your favorite TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Be sure to charge your devices fully 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 departure to account for traffic and security lines.
• Bring your own snacks and water—pack some snacks and carry a refillable water bottle to stay hydrated and save on food costs at the airport.

Tips for long-haul flights to Windham

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 provide free seat selection once online check-in opens, typically 24–48 hours before your flight. Some airlines may allow you to select your seat even earlier.
• Arrive at the airport in plenty of time—make sure to arrive at the airport at least 3 hours prior to departure for international flights to accommodate check-in, security, and immigration procedures.
• Relax at the airport—if you have some extra time, take the opportunity to browse the shops, enjoy a coffee, or unwind at the gate or in a departure lounge if you have access. Most airports offer free Wi-Fi that you can use.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and adjusting your sleep schedule to align with your destination's time zone. Aim to sleep or stay awake on the flight according to the local time at your arrival destination to help minimize jet lag.

Tips to find the cheapest flights to Windham

The cheapest day to fly

Get started finding a cheap flight to Windham 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

January is the cheapest month to fly to Windham. 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 Windham. 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 Windham, 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 Windham

The lowest price for round-trip flights to Windham in 2026 starts from $174, while one-way tickets start from from $90. 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 Windham. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Windham

Cape Air, United, American Airlines are just some of the airlines that can typically offer cheap tickets to Windham. 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 Windham and countless more destinations worldwide.

The most affordable airports to fly into

To view the cheapest airports to fly into for Windham, 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 Windham. 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 Windham 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 Windham

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 Windham.

Stopover savings

The cheapest tickets to Windham are sometimes those with a stopover. Book one of these flights, and you'll change planes at an airport en route to Windham. 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 Windham 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 Windham. Simply download the free Expedia app to your smart device and activate Windham 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 Windham. 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.