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$43 Cheap Flights to Chester, NY

View $43 flight on Sun, Nov 1, 2026Opens in a new window

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Popular airlines to Chester

How much is the cheapest flight to Chester?

Prices were available within the past 7 days and start at $43 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Allegiant Air
Fri, Nov 6 - Fri, Nov 13
SFB
Orlando
SWF
Newburgh
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Allegiant Air flight, departing Fri, Nov 6 from Orlando to Newburgh, returning Fri, Nov 13, priced at $76 just found
Allegiant Air
Fri, Nov 6 - Mon, Nov 9
SFB
Orlando
SWF
Newburgh
$82 Roundtrip, found 10 hours ago
$82
Roundtrip
found 10 hours ago
Select Allegiant Air flight, departing Fri, Nov 6 from Orlando to Newburgh, returning Mon, Nov 9, priced at $82 found 10 hours ago
Allegiant Air
Thu, Oct 22 - Sun, Oct 25
FLL
Fort Lauderdale
SWF
Newburgh
$86 Roundtrip, just found
$86
Roundtrip
just found
Select Allegiant Air flight, departing Thu, Oct 22 from Fort Lauderdale to Newburgh, returning Sun, Oct 25, priced at $86 just found
Allegiant Air
Mon, Dec 7 - Fri, Dec 11
SFB
Orlando
SWF
Newburgh
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Allegiant Air flight, departing Mon, Dec 7 from Orlando to Newburgh, returning Fri, Dec 11, priced at $88 just found
Breeze Airways
Sat, Sep 12 - Sat, Sep 19
RDU
Raleigh
SWF
Newburgh
$102 Roundtrip, found 3 hours ago
$102
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Sat, Sep 19, priced at $102 found 3 hours ago

Find the cheapest month to fly from Columbus (CMH) to New York (JFK)

April is typically the cheapest month to fly

From $160 - $432 per traveler.

Frequently asked questions

What month is the cheapest to fly to Chester?
November is the cheapest month to travel to Chester. There's less demand then, so fares are usually more affordable. Booking your trip outside of public holidays and school breaks can also help you save.
Which US cities have the cheapest flights to Chester?
Usually, Los Angeles, San Francisco and Boston have cheap flights to Chester. Flexibility, however, is always key to landing the best fares. Plan your trip during low season or midweek to keep costs to a minimum.
Which US cities fly direct to Chester?
You can fly to Chester directly from 58 US cities. To find a nonstop route, check "Direct flights only" when searching for flights to Chester on Expedia. Then, explore the options and find the best departure out of any of these cities:

  • Los Angeles
  • San Francisco
  • Boston
  • Miami
  • Orlando

How to find a cheap flight to Chester?
To lock in cheap flights to Chester, book well in advance or travel during the off-peak months of January and February. Want another helpful tip? Leave on a Thursday and save around 16% on average compared to those who travel on a Sunday.* Opt to receive price alerts on the Expedia app and we'll update you as soon as your fares drop.*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 Chester?
It's possible to get cheap deals on last-minute departures to Chester, especially if your travel plans aren't set in stone. Think about jetting out of a different airport, tweaking your trip dates or choosing another carrier to get a cheap flight to Chester.
How far in advance should I book a flight to Chester?
Secure the departure dates you want and a fare you'll love by booking your domestic flight to Chester up to 28 days in advance. Search for tickets two to four months ahead if you're jetting to Chester 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 Chester?
You can save an average of 8% if you purchase tickets on a Sunday instead of Fridays, which tend to be the most expensive day to book.* When it comes to getting a cheap flight to Chester, timing makes a difference.*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 Chester?
Chester is connected to 168 airports globally through 72 carriers, with John F. Kennedy Intl. Airport (JFK) as its chief entry point. Choose from these major airlines to Chester when planning your trip:

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

Where do you fly into Chester?
Chester's main point of arrival is Stewart Intl. Airport (SWF). If you're looking for more nearby options when flying to Chester, consider Westchester County Airport (HPN), LaGuardia Airport (LGA) or Liberty Intl. Airport (EWR). You can also fly to Chester through John F. Kennedy Intl. Airport (JFK).
How far is the airport from central Chester?
If you're arriving at Stewart Intl. Airport (SWF), you'll be approximately 14 mi northeast of central Chester.
Can I save money by booking a Chester trip package?
Bundle your accommodations and flights and you could save hundreds of dollars. What's more, you can add extras like car rentals and tours to your Chester flight and hotel package deal. With Expedia, it's easy to organize all your Chester travel arrangements in one place.
Can I change or cancel my flight to Chester?
You can often change or cancel your flight to Chester within 24 hours of booking. However, be mindful that some flights are non-refundable. In those cases, you may be issued a credit toward a future flight rather than a direct refund. Be sure to check the airline's rules and restrictions in your itinerary for specific details. You can use Expedia's "Changes included" or "No cancel fee" filters during your search to secure cheap flights to Chester with flexible change policies. For additional information, visit our Customer Service Portal.

*Flight schedules are subject to change.

*Available to One Key members.

 

Book with confidence

Tips to find the cheapest flights to Chester

The cheapest day to fly

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

The lowest price for round-trip flights to Chester in 2026 starts from from $76, while one-way tickets start from from $43. 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 Chester. If you have a preferred departure time or airline, you can use the handy filters to customize your search.

The cheapest airlines flying to Chester

Allegiant Air, Breeze Airways are just some of the airlines that can typically offer cheap tickets to Chester. 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 Chester and countless more destinations worldwide.

The most affordable airports to fly into

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

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 Chester.

Stopover savings

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

Travel information

Destination airport
Stewart Intl.
Destination airport IATA code
SWF
Destination city name
Newburgh
Roundtrip price
$76

Trending flights to Chester

Prices were available within the past 7 days and start at $43 for one-way flights and $76 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Allegiant Air
Fri, Nov 6 - Fri, Nov 13
SFB
Orlando
SWF
Newburgh
$76 Roundtrip, just found
$76
Roundtrip
just found
Select Allegiant Air flight, departing Fri, Nov 6 from Orlando to Newburgh, returning Fri, Nov 13, priced at $76 just found

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