$71 Cheap Flights to Windham, ME

Flights to Windham at a glance

Traveling to Windham is a breeze; you can easily choose from a selection of full-service or budget-friendly carriers. Compare journey times and find the best flights to Windham that align with your financial plan and itinerary for exploring the city's renowned attractions and neighborhoods.

• Major airport near Windham: Portland International Jetport Airport (PWM)
• Flights per week: 1,750+ flights arriving at Windham airport
• Number of airlines that fly to Windham: around 10+ carriers

Popular airport near Windham

Windham is a charming city perfect for those seeking outdoor activities, stunning scenery, romantic getaways, and family adventures. Travelers flock to Windham for its picturesque landscapes and recreational opportunities, and the area is conveniently served by major airports, including Windham Portland International, making it easy to plan your visit.

• Portland International Jetport Airport (PWM): Nestled in Cumberland County, Maine, approximately 9 miles from Windham, this airport offers a range of domestic and international flights. It connects to over 165 domestic cities and more than 30 international locations. Travelers can opt for enhanced comfort by choosing first class or premium economy seating, depending on the airline and route. Major airlines operating here include American Airlines, United, and Delta.

Top routes to Windham

• Orlando (MCO) to Windham (PWM), with one-way fares starting at around $70
• New York (JFK/LGA) to Windham (PWM), with one-way fares starting at around $60
• Washington (IAD/DCA) to Windham (PWM), with one-way airfare from around $90
• Chicago (ORD/MDW) to Windham (PWM), with one-way fares starting at around $90
• Tampa (TPA) to Windham (PWM), with one-way airfare from around $65

Cheapest routes to Windham

• Charleston (CHS/CRW) to Windham (PWM), with cheap one-way fares from around $50
• New York (JFK/LGA) to Windham (PWM), with cheap one-way fares from around $60
• Raleigh (RDU) to Windham (PWM), with low one-way fares from around $60
• Tampa (TPA) to Windham (PWM), with affordable one-way prices from around $65
• Norfolk (ORF) to Windham (PWM), with budget one-way fares from around $65

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

Top airlines with flights to Windham

• American Airlines: Operating flights to Portland International Jetport Airport (PWM), this airline represents roughly 36% of arrivals in Windham. The typical one-way fare is around $270, with premium service possibly including first class based on the route.
• United: With routes to Portland International Jetport Airport (PWM), United accounts for about 23% of Windham's arrivals. The average cost for a one-way ticket is approximately $310, and premium service may feature first class depending on the route.
• Delta: Providing service to Portland International Jetport Airport (PWM), Delta comprises around 21% of arrivals in Windham. One-way fares hover around $260, with premium options potentially including both premium economy and first class, depending on the route.
• Southwest Airlines: Flying into Portland International Jetport Airport (PWM), Southwest Airlines is responsible for about 12% of Windham's arrivals. The average fare for a one-way flight is approximately $270.
• Breeze: This airline flies to Portland International Jetport Airport (PWM) and contributes roughly 3% of arrivals in Windham. One-way fares with Breeze average around $120, making it an economical choice for travelers.

Best time to fly to Windham

The most popular months for travelers to fly to Windham are March, April, and July, when peak temperatures in Windham can reach up to 69.4°F in July. If you prefer quieter travel, consider January, the least busy and relatively cheaper time to visit with fewer crowds and temperatures around 24.6°F. For better deals, September usually offers the lowest average one-way fare around $215, roughly 10% cheaper than the yearly average. Looking for additional cheaper months to fly? January, August, and May offer average one-way fares of around $227, making them good options for flexible travelers.

*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 Portland International Jetport Airport, Portland Transportation Center, a train station, is located about 2.4 miles away by car, while Portland Seaport, a seaport, is about 4.2 miles away by car, and Casco Bay Lines Ferry Terminal, a ferry terminal, is approximately 4.9 miles away by car, providing convenient options for onward travel.
• 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

• Westbrook: Westbrook is located 6 miles drive away from Windham and offers a delightful mix of outdoor activities and romantic scenery. This charming city is perfect for those looking to enjoy educational experiences, shopping at local centers, and relaxing at nearby lakes and beaches. Key highlights include the University of New England, a modern college ideal for city vacations, the Cross Insurance Arena, an entertainment hub for family outings, and the Portland Museum of Art for culture enthusiasts. A visit to Westbrook promises a refreshing getaway.
• Falmouth: Falmouth is located 7 miles away from Windham and is an excellent destination for outdoor lovers seeking scenic views and romantic spots. Visitors can explore its recreational areas, enjoy educational opportunities, or hit the ski fields during winter. Local attractions include beautiful lakes and family-friendly beaches, with highlights such as the University of New England for a contemporary college experience and Mackworth Island State Park, perfect for outdoor adventures. Falmouth offers a serene escape with plenty to discover.
• Portland: Portland is located 10 miles drive away from Windham and is a vibrant city that combines outdoor fun with family-friendly attractions. Explore its dynamic arena entertainment venues and enjoy live theater and music concerts. The city boasts picturesque beaches and tranquil lakes, making it ideal for relaxation. Must-visit spots include the Cross Insurance Arena for entertainment, the University of New England for educational pursuits, and the Portland Museum of Art for cultural experiences. Portland invites travelers to immerse themselves in its lively atmosphere.

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 traveling with budget airlines, it’s often more economical to stick to a carry-on. Optimize space by using mini toiletries, wearing your heaviest clothes, and planning your outfits wisely. This strategy also allows you to bypass waiting at baggage claim upon arrival.
• Bring your own entertainment—short-haul flights frequently lack in-flight entertainment options. To keep yourself entertained, download TV shows, movies, music, or podcasts ahead of time, and consider bringing a book. Remember to fully charge your devices before you board.
• Arrive at the airport in plenty of time—for both short and domestic flights, it’s advisable to arrive at least 1.5 to 2 hours prior to departure, taking into account potential traffic and security wait times.
• Bring your own snacks and water—pack some snacks and a refillable water bottle to stay hydrated and save money while 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 your comfort. Full-service airlines typically allow free seat selection once online check-in opens, which is usually 24–48 hours prior to your flight. Some airlines may offer seat selection even earlier than this.
• Arrive at the airport in plenty of time—aim to arrive at the airport at least 3 hours before departure for international flights to allow sufficient time for check-in, security, and immigration procedures.
• Relax at the airport—if you have some extra time, take a moment to browse the shops, grab a coffee, or unwind at the gate or in a departure lounge, if you have access. Airport Wi-Fi is generally free and available.
• Adjust to the new time zone mid-flight—begin syncing your body clock by changing your watch and modifying your 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 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

November 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 $142, while one-way tickets start from from $71. 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

Breeze Airways, United, Southwest Airlines, Delta, 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.