Cheap Flights to Chestertown, NY

Popular airlines to Chestertown

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Frequently asked questions

What month is the cheapest to fly to Chestertown?
The cheapest month to fly to Chestertown is when there's less demand. Off-peak months are often when you'll find cheap flights. To save money, steer clear of flying during school breaks and major holidays.
Which US cities have the cheapest flights to Chestertown?
Chicago, Washington and Baltimore usually have cheap flights to Chestertown. Remember that fares vary based on factors like demand, time of year and number of stopovers.
Which US cities fly direct to Chestertown?
Choose from 16 US cities with direct flights to Chestertown. When reserving on Expedia, check "Direct flights only" to compare nonstop options. Fly to Chestertown from any of these leading cities:

  • Chicago
  • Washington
  • Baltimore
  • Detroit
  • Orlando

How to find a cheap flight to Chestertown?
To secure cheap flights to Chestertown, book in advance or travel during the off-peak months of January and May. Like another tip? Depart on a Thursday and save around 16% on average compared to traveling on a Sunday.* Set up price tracking on the Expedia app and you'll get notified 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 Chestertown?
It's possible to get great deals on last-minute departures to Chestertown, especially if your plans aren't set in stone. Consider leaving from a different hub, changing your dates or selecting an alternative carrier to get a cheap flight to Chestertown.
How far in advance should I book a flight to Chestertown?
For some of the best deals on domestic journeys, book your flight to Chestertown 28 days ahead of your travel dates. For international flights, search for your ticket two to four months in advance. This boosts your chances of getting the departure dates and times you want.**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 Chestertown?
You'll save an average of 8% by buying tickets on a Sunday rather than Fridays, which tend to be the most expensive day to book.* When it comes to scoring a cheap flight to Chestertown, it's all about timing.*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 Chestertown?
Whether you'd like to sit in a premium seat or cut costs in economy, these popular airlines will fly you to Chestertown:

  • American Airlines - 394 flights to Chestertown each month, including 394 flights to Albany Intl. Airport (ALB) per month.
  • Delta Air Lines - 260 flights to Chestertown each month, including 260 flights to Albany Intl. Airport (ALB) per month.

Where do you fly into Chestertown?
When you're flying to Chestertown, the main airport to arrive at is Rutland Southern Vermont Regional Airport (RUT). You can also jet into nearby hubs like Adirondack Regional Airport (SLK), Glens Falls, NY (GFL-Floyd Bennett Memorial) or Lake Placid, NY (LKP). Another possibility to think about when you fly to Chestertown is Schenectady County Airport (SCH).
How far is the airport from central Chestertown?
If you're flying into Rutland Southern Vermont Regional Airport (RUT), you'll be around 45 mi east of central Chestertown.
Can I save money by booking a Chestertown trip package?
Book a Chestertown flight and hotel package deal on Expedia, and you could make significant savings. It's easy to bundle your accommodations and flights, and you can also add car rentals and tours to create your own personalized Chestertown vacation. Plus, nothing beats the convenience of booking everything in one place.
Can I change or cancel my flight to Chestertown?
You can usually change or cancel your flight to Chestertown within 24 hours of booking. However, keep in mind that some flights are non-refundable. In those cases, you may receive a credit toward a future trip in place of a direct refund. It's important to check the airline's rules and restrictions in your itinerary for specific details. Use Expedia's "No cancel fee" or "Changes included" filters during your search to secure cheap flights to Chestertown with flexible change policies. To learn more, visit our Customer Service Portal.

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Tips to find the cheapest flights to Chestertown

The cheapest day to fly

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

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

The cheapest airlines flying to Chestertown

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

The most affordable airports to fly into

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

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 Chestertown.

Stopover savings

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

Travel information

Destination airport
Chestertown
Destination airport IATA code
GFL

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*Available to One Key members.