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Chester

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Chester Flights as Low as $314

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Fri, Nov 8 - Sat, Nov 9
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 9, priced at $314 found 1 day ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$324 Roundtrip, found 23 hours ago
$324
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $324 found 23 hours ago
Delta
Tue, Nov 5 - Tue, Nov 5
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Nov 5 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Tue, Nov 5, priced at $324 found 1 day ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$334 Roundtrip, found 23 hours ago
$334
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $334 found 23 hours ago
American Airlines
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$334 Roundtrip, found 23 hours ago
$334
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $334 found 23 hours ago
Delta
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$339 Roundtrip, found 23 hours ago
$339
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $339 found 23 hours ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$343 Roundtrip, found 23 hours ago
$343
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $343 found 23 hours ago
American Airlines
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 23 hours ago
$344
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $344 found 23 hours ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$348 Roundtrip, found 23 hours ago
$348
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $348 found 23 hours ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$353 Roundtrip, found 23 hours ago
$353
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $353 found 23 hours ago
Delta
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$354 Roundtrip, found 23 hours ago
$354
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $354 found 23 hours ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$358 Roundtrip, found 23 hours ago
$358
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $358 found 23 hours ago
Delta
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$364 Roundtrip, found 23 hours ago
$364
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $364 found 23 hours ago
Delta
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$364 Roundtrip, found 23 hours ago
$364
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $364 found 23 hours ago
JetBlue Airways
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$368 Roundtrip, found 23 hours ago
$368
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $368 found 23 hours ago
Delta
Fri, Nov 8 - Sun, Nov 10
JFK
John F. Kennedy Intl.
RUT
Rutland Southern Vermont Regional
$369 Roundtrip, found 23 hours ago
$369
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Nov 8 from John F. Kennedy Intl. to Rutland Southern Vermont Regional, returning Sun, Nov 10, priced at $369 found 23 hours ago

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Hartness State Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $314, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $314 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$313

Last Minute Hotel Deals in Chester

Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
3 out of 5
698 VT-11, Chester, VT
The price is $244 per night from Sep 23 to Sep 24
$244
includes taxes & fees
Sep 23 - Sep 24
Stay at this 3-star B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (63 reviews)
Friendly, kind, comfortable
"Very kind and courteous people running the Inn. They've done a lot of upkeep, and the property is lovely. I had the room at the top, which was a bit cramped, but it was clean and comfortable. The grounds are lovely and the dinner service was excellent. Breakfast gave you a choice, which was a nice ..."

Reviewed on Sep 20, 2024

Stone Hearth Inn and Eatery
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $129 per night from Sep 23 to Sep 24
$129
includes taxes & fees
Sep 23 - Sep 24
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
"Very nice place to stay"

Reviewed on Sep 11, 2024

Colonial Motel And Spa
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $710 per night from Oct 21 to Oct 22
$710
includes taxes & fees
Oct 21 - Oct 22
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (466 reviews)
"Wonderful hotel. Wonderful facilities."

Reviewed on Sep 19, 2024

Woodstock Inn & Resort
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
The price is $362 per night from Sep 23 to Sep 24
$362
includes taxes & fees
Sep 23 - Sep 24
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our ...
7.2/10 Good! (407 reviews)
"A beautiful hotel in a beautiful setting."

Reviewed on Sep 19, 2024

The Equinox Golf Resort & Spa
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is $121 per night from Sep 23 to Sep 24
$121
includes taxes & fees
Sep 23 - Sep 24
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8/10 Very Good! (1,005 reviews)
"Ok, but tv did not work."

Reviewed on Sep 20, 2024

The Covered Bridge Inn
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
The price is $347 per night from Oct 23 to Oct 24
$347
includes taxes & fees
Oct 23 - Oct 24
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (625 reviews)
"Everything was great! We were well cared for…and so was the property."

Reviewed on Sep 18, 2024

The Shire Woodstock
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 out of 5
4519 Main St, Manchester Center, VT
The price is $204 per night from Oct 23 to Oct 24
$204
includes taxes & fees
Oct 23 - Oct 24
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
9.6/10 Exceptional! (1,003 reviews)
"The hotel was excellent!"

Reviewed on Sep 19, 2024

Hampton Inn and Suites Manchester
The Black Bear Lodge at Stratton Mountain Resort
The Black Bear Lodge at Stratton Mountain Resort
3 out of 5
5 Village Lodge Road, Stratton, VT
The price is $149 per night from Sep 23 to Sep 24
$149
includes taxes & fees
Sep 23 - Sep 24
Stay at this 3-star ski resort in Stratton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
7.4/10 Good! (845 reviews)
"Liked your staff. Very helpful"

Reviewed on Sep 19, 2024

The Black Bear Lodge at Stratton Mountain Resort
See all 2,825 properties in Chester
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.