Cheap Flight Deals to Chester NY from CA $228

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How to find cheap flights to Chester?

The cheapest prices found with in the last 7 days for return flights were CA $441 and CA $228 for one-way flights to Chester for the period specified. Prices and availability are subject to change. Additional terms apply

Fri., 14 Mar. - Fri., 21 Mar.
CPH
Kastrup
SWF
Stewart Intl.
CA $441 Roundtrip, found 1 day ago
CA $441
Roundtrip
found 1 day ago
Select Fly Play flight, departing Fri., 14 Mar. from Kastrup to Stewart Intl., returning Fri., 21 Mar., priced at CA $441 found 1 day ago

Your guide to flights to Chester, NY

Fly Play fly to Chester, so use Travelocity to search, find, and compare some truly tempting deals from the 2 airlines—that way you can be sure you’ve found the best deal for you. A flight to Chester NY currently costs between CA $441 and CA $441. Prices vary, but for the best fares, travel in June when prices are at their lowest.  

Top tips for finding cheap flights to Chester  

The cheapest flight for a round trip to Chester is currently CA $441. When you search for flights to Chester, enter your preferred travel dates then click on ‘flexible dates’ to compare cheap flight tickets to Chester for nearby days.  The cheapest month to travel to Chester is March from our list of deals available.  

But if you’re flexible about when you travel, you can find great deals on flights across the year. If you’re planning a vacation, you can save more on Travelocity when you bundle flights with car rental and hotel bookings, too. Many airlines currently offer flexible booking options, so look for flights offering no change fees.   

How to cancel flights to Chester 

We know plans change, that’s why at Travelocity, we make it as easy as possible for you to cancel or amend your plane tickets. Go to My Trips, enter your itinerary number, then follow the instructions. Many airlines let you cancel flights online free of charge if you booked it in the last 24 hours. Visit Customer Service for more advice.  

Why you should book your flight to Chester with Travelocity 

We have top deals on plane tickets even for last minute flights to Chester, so you can simply type in your travel dates and compare our best prices. Booking with Travelocity means you get flexible cancellation options, 24/7 support, and, thanks to our Price Match Promise, if the airfare drops after you book, you can get a refund! Whether you’re planning a business trip, weekend getaway, or a family vacation—let Travelocity get you to Chester for less. 

Find The Perfect Hotel For After Your Flight

Family Friendly Hotels in Chester

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel

2.5 out of 5
2 Bryle Place, Chester, NY
The price is CA $132 per night from Dec. 10 to Dec. 11
CA $132
CA $150 total
includes taxes & fees
10 Dec - 11 Dec
Book a stay at this business-friendly hotel in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,001 reviews)
"Good hotel for the price. Direct tv sucks"

Reviewed on 22 Nov. 2024

Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best Chester Flight and Hotel Packages

Chester flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Dec. 27 - Dec. 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newburgh (SWF)
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
per person
Dec. 27 - Jan. 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
per person
Dec. 27 - Jan. 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Newburgh (SWF)
Don't see what you're looking for?
See all available trips from Toronto to Chester
View all trips

Need a car after flight to Chester?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Chester?
20 airlines offer flights to the city of Chester, making it one of the world’s most frequented airline hubs. Most savvy travelers choose to fly with these carriers:

  • Delta Air Lines
  • United Airlines
  • American Airlines

What airport is best to fly into Chester?
Who looks forward to getting stuck in bumper-to-bumper traffic while on their way to a flight on the opposite end of the city? Wander wisely. Chester is serviced by a few airports, so consider which one is closest to where you’ll be spending most of your time. Here are the city’s key airports:

  • John F. Kennedy Intl. Airport (JFK) – 88 kilometers from downtown
  • EWR – 72 kilometers from downtown
  • LaGuardia Airport – 72 kilometers from downtown

Where to stay in Chester
Whether you’re visiting Chester on a family vacation, for work or something else, we’re confident you’ll find the perfect place to crash. Travelocity offers at least 66 accommodations within easy reach of the heart of town.The Holiday Inn Express Hotel & Suites Chester, an IHG Hotel and the Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries are our top accommodations in Chester. Make a reservation and then get down to the fun stuff — booking your amazing getaway experiences.
Places to visit in Chester
0 Seeking some more ideas? 0 But that’s not all. 0
How to get through airport security fast when traveling to Chester
Make your flight to Chester a little bit easier by following these useful security tips:

  • Keep your travel ID and boarding pass in an easily accessible place. They’ll be the first things you’ll be asked for by airport security staff.
  • USB sticks, wallets and power banks must be put in a bin for X-raying. If you pass through the body scanner with any of these items, you’ll be asked to turn back and remove them.
  • Digital cameras, laptops and other electronic devices must be placed in separate bins to be X-rayed.
  • When you approach the security checkpoint, you’ll be asked to place all creams, gels and liquids in a separate tub for inspection. Make sure they’re all in containers no larger than 3.4 ounces (100 milliliters) and sealed in a clear zip-lock bag.
  • Construction boots and other cumbersome shoes are usually X-rayed at the security checkpoint. It might be wise to wear simple sneakers instead.
  • Pack any pocketknives or other pointy metal items inside your checked luggage. Security personnel don’t allow these on the aircraft.

Plane Tickets To Chester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Chester. Browse through our inventory to explore a wide range of cheap flights to Chester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Chester as you anxiously await to exit the plane and explore what Chester has to offer. Considering all the amazing local food and culture in Chester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Chester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Chester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Chester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Chester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.