Cheap Flights to Woodstock, NY

Popular airlines to Woodstock

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Frequently asked questions

What month is the cheapest to fly to Woodstock?
Schedule your trip for if you're looking for a good price on your fare. It's the cheapest month to fly to Woodstock. Try to avoid traveling during busy periods such as public holidays or major events.
Which US cities have the cheapest flights to Woodstock?
Score cheap flights to Woodstock from Chicago, Washington and Baltimore. These cities usually offer the best fares to this popular destination. But bear in mind that stopovers, seasonality and demand will also influence rates, so stay flexible and book when you spot a bargain.
Which US cities fly direct to Woodstock?
Take your pick of 16 US destinations that have direct flights to Woodstock. When booking on Expedia, check "Direct flights only" to compare nonstop routes. Fly to Woodstock from any of these leading cities:

  • Chicago
  • Washington
  • Baltimore
  • Detroit
  • Orlando

How to find a cheap flight to Woodstock?
To get cheap flights to Woodstock, book well in advance and travel during the off-season months of January and May. Want another tip? Take off on a Thursday and save 16% on average compared to those who travel on a Sunday.* Set up price tracking on the Expedia app and we'll update you as soon as your fares go down.*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 Woodstock?
Staying flexible about your travel plans may help you to find last-minute deals on cheap flights to Woodstock. To view all the available options, consider exploring different ticket types, tweaking your Woodstock vacation dates, flying out of an alternative airport or going with another airline.
How far in advance should I book a flight to Woodstock?
Book your flight to Woodstock two to four months ahead if you're flying in from an international destination. For domestic travel, the recommendation is around 28 days in advance. Lower prices and a greater choice of travel dates, schedules and seating options are just some of the perks of booking early.**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 Woodstock?
Sundays are typically the best day to book a cheap flight to Woodstock, with savings of around 8% on average compared to a Friday. If you choose to purchase on a Friday, expect to pay a higher price as this is typically 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 Woodstock?
A total of 4 carriers connect 12 airports all over the world to Woodstock. Here are a few of the leading airlines to Woodstock, where Albany Intl. Airport (ALB) is the major arrival point:

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

Where do you fly into Woodstock?
When flying to Woodstock, the main airport to arrive at is Stewart Intl. Airport (SWF). You can also jet into nearby hubs like Albany Intl. Airport (ALB), Hudson, NY (HCC-Columbia County) or Dutchess County Airport (POU). Another option to consider when you fly to Woodstock is Montgomery, NY (MGJ-Orange County).
How far is the airport from central Woodstock?
You'll be around 35 mi south of the center of Woodstock after jetting into Stewart Intl. Airport (SWF).
Can I save money by booking a Woodstock trip package?
Book a Woodstock flight and hotel package deal on Expedia, and you can benefit from significant savings. It's easy to bundle your hotel and flight, and you can also add car rentals and activities to create your own personalized Woodstock getaway. Plus, there's nothing like the convenience of booking everything in one place.
Can I change or cancel my flight to Woodstock?
It's often possible to change or cancel your flight to Woodstock. Many airlines allow you to cancel flights for free within 24 hours of booking. However, some flights are non-refundable, and airlines may issue you a credit toward a future trip in place of a direct refund. To reserve cheap flights to Woodstock with flexible change policies, check "Changes included" or "No cancel fee" when you search. Looking for more information? Go to our Customer Service Portal.

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Tips to find the cheapest flights to Woodstock

The cheapest day to fly

Get started finding a cheap flight to Woodstock 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 Woodstock. 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 Woodstock. 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 Woodstock, 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 Woodstock

The lowest price for round-trip flights to Woodstock 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 Woodstock. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Woodstock

are just some of the airlines that can typically offer cheap tickets to Woodstock. 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 Woodstock and countless more destinations worldwide.

The most affordable airports to fly into

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

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 Woodstock.

Stopover savings

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

Tips to find the cheapest flights to Woodstock

Travel information

Destination airport
Woodstock
Destination airport IATA code
POU

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*Available to One Key members.