Cheap Flights to Windham, NY

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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

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 2025 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 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

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.

Frequently asked questions

What month is the cheapest to fly to Windham?
July is generally the least expensive month for flights to Windham*. Be sure to check for affordable fares during this time as you may be able to bag a bargain. *Cheapest month to fly is based on the month with the cheapest flight found on Expedia.com in the next 330 days.
Which US cities have the cheapest flights to Windham?
Generally, Chicago, Washington and Baltimore have cheap flights to Windham. However, being flexible is the secret to scoring the best prices. Plan your getaway midweek or during the off-peak season to keep costs down.
Which US cities fly direct to Windham?
You can fly to Windham directly from 16 US destinations. To find a nonstop route, check “Direct flights only” when looking for flights to Windham on Expedia. Then, explore the options and find the best departure out of any of these cities:

  • Chicago
  • Washington
  • Baltimore
  • Detroit
  • Orlando

How to find a cheap flight to Windham?
Book in advance for the best chance of scoring cheap flights to Windham. Also, consider traveling during off-peak months like March and April. If you fly on a Thursday, you can save an average of 16% compared to those departing on a Sunday.* Save time checking every day and set up a price alert on the Expedia app. We’ll let you know when fares change.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Windham?
Being flexible with your travel plans might help you to secure last-minute offers on cheap flights to Windham. To view all the available options, consider exploring different ticket types, tweaking your Windham trip dates, jetting out of an alternative airport or using another airline.
How far in advance should I book a flight to Windham?
Find the departure dates you want and a fare that works with your budget by booking your domestic flight to Windham up to 28 days in advance. Search for tickets between two and four months ahead if you’re traveling to Windham from an international destination.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Windham?
Sundays are typically the best day to book a cheap flight to Windham, with savings of around 8% on average compared to a Friday. If you decide to buy tickets on a Friday, be ready to pay a higher price as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation’s (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Windham?
Windham has connections to 12 airports worldwide through 4 carriers, with Albany Intl. Airport (ALB) as its chief gateway. Select from these leading airlines to Windham when planning your journey:

  • Delta Air Lines
  • American Airlines
  • United Airlines
  • JetBlue Airways

Where do you fly into Windham?
Windham’s main gateway is Albany Intl. Airport (ALB). If you want other nearby options when flying to Windham, check out Stewart Intl. Airport (SWF), Hudson, NY (HCC-Columbia County) or Schenectady County Airport (SCH). You can also fly to Windham through Great Barrington, MA (GBR-Walter J. Koladza).
How far is the airport from central Windham?
If you’re touching down at Albany Intl. Airport (ALB), you’ll be about 40 mi northeast of the center of Windham.
Can I save money by booking a Windham trip package?
You could potentially save hundreds of dollars if you choose a Windham flight and hotel package deal on Expedia. And you’ll save time and hassle by having all your travel arrangements in one place. Try bundling your hotel and flight with extras such as car rentals and activities for your own customized Windham getaway.
Can I change or cancel my flight to Windham?
If you bought your flight to Windham within the last 24 hours, you can usually change or cancel it without fees. After that, additional charges may apply depending on the airline’s terms and conditions. For more information, visit our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be issued a credit toward a future flight in place of a direct refund. When browsing Expedia, use the “Changes included” or “No cancel fee” filters to compare tickets with flexible change policies.
Flights to Windham information
Destination airport
Windham
Destination airport IATA code
HCC

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