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Chester

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Chester Flights as Low as $134

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

JetBlue Airways
Sun, May 24 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$134 Roundtrip, found 4 hours ago
$134
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sun, May 24 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $134 found 4 hours ago
JetBlue Airways
Sat, May 23 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 4 hours ago
$163
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $163 found 4 hours ago
JetBlue Airways
Thu, May 21 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Thu, May 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $167 found 4 hours ago
JetBlue Airways
Wed, May 20 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 4 hours ago
$178
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, May 20 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $178 found 4 hours ago
Cape Air
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 2 hours ago
$180
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $180 found 2 hours ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 3 hours ago
$183
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $183 found 3 hours ago
JetBlue Airways
Sat, Apr 25 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Apr 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $183 found 3 days ago
Cape Air
Mon, May 18 - Thu, Jun 4
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 4 hours ago
$184
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Mon, May 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 4, priced at $184 found 4 hours ago
Cape Air
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 2 hours ago
$186
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $186 found 2 hours ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 3 hours ago
$188
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $188 found 3 hours ago
Cape Air
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 3 hours ago
$189
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $189 found 3 hours ago
Cape Air
Sat, May 23 - Sun, Jun 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 4 hours ago
$190
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 7, priced at $190 found 4 hours ago
JetBlue Airways
Sat, Apr 18 - Sun, May 3
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, May 3, priced at $193 found 2 days ago
Cape Air
Wed, May 20 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 4 hours ago
$194
Roundtrip
found 4 hours ago
Select Cape Air flight, departing Wed, May 20 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $194 found 4 hours ago
JetBlue Airways
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 2 hours ago
$196
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $196 found 2 hours ago
Cape Air
Sat, May 23 - Sun, Jun 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 14 hours ago
$196
Roundtrip
found 14 hours ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 7, priced at $196 found 14 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 May, 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 $134, 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 $134 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$134

Last Minute Hotel Deals in Chester

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.2/10 Very Good! (430 reviews)
The carpets could have been vacuumed and it was overpriced for what it was.

Reviewed on Apr 10, 2026

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Fullerton Inn
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (118 reviews)
Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking.

Reviewed on Mar 29, 2026

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Stone Hearth Inn and Eatery
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,001 reviews)
Room was perfect (king bed), and big. Hot tub was wonderful after skiing all day and hot, but jets could have been stronger. Staff efficient and very friendly. Location great-10 minutes from Okemo. Will definitely come back!

Reviewed on Apr 10, 2026

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Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
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. ...
9.4/10 Exceptional! (572 reviews)
Wonderful historic property with warm and thoughtful staff. Even though some areas in the lobby were being refurbished, we still enjoyed the experience. Look forward to returning when the huge fireplace in the lobby is back up and operational.

Reviewed on Apr 10, 2026

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Woodstock Inn & Resort
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this 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 (1,001 reviews)
Awesome and clean and quiet love the staff

Reviewed on Apr 14, 2026

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Colonial Motel And Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
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! (1,000 reviews)
Well managed and clean property. Phenomenal breakfast and started serving at 6am!

Reviewed on Apr 14, 2026

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Hampton Inn and Suites Manchester
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (929 reviews)
it's all good

Reviewed on Apr 2, 2026

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The Palmer House Resort, an Ascend Collection Hotel
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ...
8.8/10 Excellent! (85 reviews)
Beautifully modernized Inn. Well maintained and very clean. The entire check in/out process was smooth, hot tub was easy to use, and the room was impeccable. 100% recommend to anyone. For the skiers/boarders, they even have a whole room with boot dryers, no more resorting to hair dryers!

Reviewed on Apr 13, 2026

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Hideaway Inn Mt. Snow
See all 3,097 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.