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Chester

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Chester Flights as Low as $373

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

JetBlue Airways
Thu, Dec 5 - Mon, Dec 16
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$373 Roundtrip, found 23 hours ago
$373
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Thu, Dec 5 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Mon, Dec 16, priced at $373 found 23 hours ago
JetBlue Airways
Tue, Dec 10 - Thu, Dec 12
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$378 Roundtrip, found 23 hours ago
$378
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Tue, Dec 10 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Thu, Dec 12, priced at $378 found 23 hours ago
JetBlue Airways
Mon, Dec 9 - Mon, Dec 16
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$383 Roundtrip, found 23 hours ago
$383
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Mon, Dec 9 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Mon, Dec 16, priced at $383 found 23 hours ago
United
Sun, Dec 8 - Tue, Dec 10
IAD
Washington Dulles Intl.
RUT
Rutland Southern Vermont Regional
$384 Roundtrip, found 23 hours ago
$384
Roundtrip
found 23 hours ago
Select United flight, departing Sun, Dec 8 from Washington Dulles Intl. to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $384 found 23 hours ago
Delta
Mon, Dec 9 - Thu, Dec 12
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$384 Roundtrip, found 23 hours ago
$384
Roundtrip
found 23 hours ago
Select Delta flight, departing Mon, Dec 9 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Thu, Dec 12, priced at $384 found 23 hours ago
JetBlue Airways
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$388 Roundtrip, found 23 hours ago
$388
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $388 found 23 hours ago
United
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$388 Roundtrip, found 23 hours ago
$388
Roundtrip
found 23 hours ago
Select United flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $388 found 23 hours ago
JetBlue Airways
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$393 Roundtrip, found 23 hours ago
$393
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $393 found 23 hours ago
Delta
Fri, Dec 6 - Fri, Dec 6
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$394 Roundtrip, found 23 hours ago
$394
Roundtrip
found 23 hours ago
Select Delta flight, departing Fri, Dec 6 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Fri, Dec 6, priced at $394 found 23 hours ago
JetBlue Airways
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$398 Roundtrip, found 23 hours ago
$398
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $398 found 23 hours ago
JetBlue Airways
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$403 Roundtrip, found 23 hours ago
$403
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $403 found 23 hours ago
United
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$403 Roundtrip, found 23 hours ago
$403
Roundtrip
found 23 hours ago
Select United flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $403 found 23 hours ago
American Airlines
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$410 Roundtrip, found 23 hours ago
$410
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $410 found 23 hours ago
Delta
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$414 Roundtrip, found 23 hours ago
$414
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $414 found 23 hours ago
American Airlines
Sun, Dec 8 - Tue, Dec 10
DCA
Ronald Reagan Washington National
RUT
Rutland Southern Vermont Regional
$415 Roundtrip, found 23 hours ago
$415
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Sun, Dec 8 from Ronald Reagan Washington National to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $415 found 23 hours ago
Delta
Sun, Dec 8 - Tue, Dec 10
BWI
Baltimore Washington Intl. Thurgood Marshall
RUT
Rutland Southern Vermont Regional
$470 Roundtrip, found 23 hours ago
$470
Roundtrip
found 23 hours ago
Select Delta flight, departing Sun, Dec 8 from Baltimore Washington Intl. Thurgood Marshall to Rutland Southern Vermont Regional, returning Tue, Dec 10, priced at $470 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 December, 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 $373, 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 $373 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$373

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 Nov 14 to Nov 15
$244
includes taxes & fees
Nov 14 - Nov 15
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! (73 reviews)
"If you’re looking for an authentic experience in a 200 year old home - with tons of wonderful history and true early American character - you’ll love this stay! This is NOT a shiny new hotel, with all the conveniences. You can forget your free “make-your-own hot breakfast” deal. This chef-curated ..."

Reviewed on Oct 12, 2024

Stone Hearth Inn and Eatery
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 $175 per night from Nov 14 to Nov 15
$175
includes taxes & fees
Nov 14 - Nov 15
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! (872 reviews)
"Pleasant staff and good location. dorm line feel to facility."

Reviewed on Nov 6, 2024

The Black Bear Lodge at Stratton Mountain Resort
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $384 per night from Dec 1 to Dec 2
$384
includes taxes & fees
Dec 1 - Dec 2
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! (480 reviews)
"Lovely hotel. Could do with some updates in areas but a very unique picturesque place ."

Reviewed on Nov 8, 2024

Woodstock Inn & Resort
The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is $115 per night from Nov 14 to Nov 15
$115
includes taxes & fees
Nov 14 - Nov 15
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! (1,003 reviews)
Good motel for the price.
"Good motel for the pice"

Reviewed on Nov 11, 2024

The Covered Bridge Inn
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $129 per night from Nov 14 to Nov 15
$129
includes taxes & fees
Nov 14 - Nov 15
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 ...
6.6/10 (1,006 reviews)
"Room was clean and comfortable. Continental breakfast was good. Conventionally located."

Reviewed on Nov 3, 2024

Colonial Motel And Spa
Mount Snow Grand Summit Resort
Mount Snow Grand Summit Resort
3 out of 5
89 Grand Summit Way, West Dover, VT
The price is $178 per night from Nov 14 to Nov 15
$178
includes taxes & fees
Nov 14 - Nov 15
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are ...
8.8/10 Excellent! (164 reviews)
"My wife and I recently celebrated our first wedding anniversary here, and we couldn’t have imagined a more perfect getaway. From the moment we arrived, the warmth of the staff, especially Joel, set the tone for our entire stay. Joel went above and beyond to ensure we had the experience we hoped for, ..."

Reviewed on Nov 8, 2024

Mount Snow Grand Summit Resort
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 out of 5
4519 Main St, Manchester Center, VT
The price is $156 per night from Dec 1 to Dec 2
$156
includes taxes & fees
Dec 1 - Dec 2
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! (1,006 reviews)
"Easy checkin, close to all amenities"

Reviewed on Nov 11, 2024

Hampton Inn and Suites Manchester
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is $177 per night from Nov 14 to Nov 15
$177
includes taxes & fees
Nov 14 - Nov 15
Stay at this 3.5-star spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (760 reviews)
"Desk staff excellent. Maintenance employee Rick very helpful."

Reviewed on Nov 4, 2024

Pointe at Castle Hill Resort
See all 2,873 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.