$94 Find Cheap Flights to Chester

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chester departing on 8/15. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chester

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Cheap Flight Deals to Chester

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights to Chester that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals to Chester

KAYAK's recommended round-trip deals from the most popular airlines that fly to Chester.
Discover the best prices for you by selecting your travel dates on KAYAK.
JetBlue Logo
8:53 am - 9:56 amBOS-RUT
1h 03mnonstop
JetBlue Logo
12:00 pm - 1:08 pmRUT-BOS
1h 08mnonstop
$173JetBlue
Find Deal
Wed, May 14 - Sun, May 18
Cape Air Logo
5:45 pm - 7:05 pmBOS-RUT
1h 20mnonstop
Cape Air Logo
7:20 am - 8:37 amRUT-BOS
1h 17mnonstop
$183Cape Air
Find Deal
Fri, Jun 20 - Sun, Jun 22
JetBlue Logo
1:49 pm - 2:52 pmBOS-RUT
1h 03mnonstop
JetBlue Logo
12:00 pm - 1:08 pmRUT-BOS
1h 08mnonstop
$193JetBlue
Find Deal
Fri, May 16 - Sun, May 18
JetBlue Logo
7:45 am - 2:52 pmATL-RUT
7h 07m1 stop
JetBlue Logo
4:10 pm - 11:43 pmRUT-ATL
7h 33m1 stop
$399JetBlue
Find Deal
Wed, May 21 - Sat, May 31
JetBlue Logo
7:45 am - 2:52 pmATL-RUT
7h 07m1 stop
JetBlue Logo
4:10 pm - 11:21 pmRUT-ATL
7h 11m1 stop
$409JetBlue
Find Deal
Tue, May 20 - Tue, Jun 3
JetBlue Logo
7:45 am - 2:52 pmATL-RUT
7h 07m1 stop
JetBlue Logo
12:00 pm - 6:19 pmRUT-ATL
6h 19m1 stop
$419JetBlue
Find Deal
Tue, May 20 - Mon, Jun 2
JetBlue Logo
7:30 am - 1:32 pmTPA-RUT
6h 02m1 stop
JetBlue Logo
3:58 pm - 11:59 pmRUT-TPA
8h 01m1 stop
$443JetBlue
Find Deal
Sat, Oct 4 - Sat, Oct 4
JetBlue Logo
6:00 am - 1:32 pmTPA-RUT
7h 32m1 stop
JetBlue Logo
3:58 pm - 11:35 pmRUT-TPA
7h 37m1 stop
$449JetBlue
Find Deal
Tue, Jun 17 - Fri, Jun 27
 Logo
3:15 pm - 9:56 amDCA-RUT
18h 41m1 stop
 Logo
4:10 pm - 12:00 pmRUT-DCA
19h 50m1 stop
Wed, May 14 - Sun, May 18
JetBlue Logo
6:00 am - 1:32 pmTPA-RUT
7h 32m1 stop
JetBlue Logo
3:58 pm - 11:18 pmRUT-TPA
7h 20m1 stop
$459JetBlue
Find Deal
Mon, Jun 23 - Wed, Jul 2
Useful Info

Good to know - Book Cheap Chester Plane Tickets

Low seasonOctober
High seasonSeptember
Cheapest flight$94
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Boston to Rutland

FAQs - booking Chester flights

  • How long is the flight to Chester?

    Flights from Boston1h 09m
  • How to fly to Chester?

    You cannot fly directly to Chester. KAYAK recommends you fly to Rutland (RUT) (25.38 miles from Chester). From there you can rent a car or get a taxi.

  • What airports are near Chester?

    The closest airport is Rutland (RUT) (25.38 mi). Other nearby airports are Lebanon Municipal (LEB) (29.02 mi), Manchester (MHT) (62.79 mi), Albany Intl (ALB) (70.66 mi) or Worcester (ORH) (77.81 mi). KAYAK recommends you fly to Rutland.

  • How far is Rutland Airport from central Rutland?

    There are 6 miles between Rutland city center and Rutland Airport.

  • What is the name of Rutland’s airport?

    There is only 1 airport in Rutland, called Rutland Airport (RUT). It can also be referred to as Rutland.

  • How does KAYAK find such low prices on flights to Chester?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chester.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chester?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chester is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chester?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chester with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chester?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chester up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chester

  • There is no major airport in Chester. It is instead served by Rutland Airport.
  • Looking for cheap airfare to Chester? 25% of our users found round-trip tickets to Chester for the following prices or less: From Boston $83
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chester flight deals.

Top airlines flying to Chester

Need help choosing which airline to fly with from the United States to Chester? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.1
Cape AirOverall score based on 34 reviews
8.7Comfort
8.9Boarding
8.9Entertainment
9.2Crew
8.6Food
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The flight was delayed for 4 hours. Once onboard the crew was wonderful.

Overall was excellent. Will definitely us JetBlue in the future.

I rate it is good we had a 4-hour travel delay at one point but JetBlue gave out food vouchers and travel points credits for another flight so they try to make up for it

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

Everything you need to know for your flight to Chester

Complete your trip to Chester with a hotel stay or car rental

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.