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Chester

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Chester Flights as Low as $155

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

JetBlue Airways
Tue, Apr 21 - Wed, Apr 29
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Apr 29, priced at $155 found 1 day ago
JetBlue Airways
Wed, Apr 22 - Wed, Apr 29
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$166 Roundtrip, found 1 day ago
$166
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Apr 22 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Apr 29, priced at $166 found 1 day ago
JetBlue Airways
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 9 hours ago
$178
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $178 found 9 hours ago
Cape Air
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$179 Roundtrip, found 9 hours ago
$179
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $179 found 9 hours ago
Cape Air
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 9 hours ago
$180
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $180 found 9 hours ago
JetBlue Airways
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 9 hours ago
$183
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $183 found 9 hours ago
Cape Air
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 9 hours ago
$186
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $186 found 9 hours ago
JetBlue Airways
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 9 hours ago
$189
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $189 found 9 hours ago
Cape Air
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 15 hours ago
$189
Roundtrip
found 15 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $189 found 15 hours ago
Cape Air
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 10 hours ago
$190
Roundtrip
found 10 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $190 found 10 hours ago
JetBlue Airways
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 15 hours ago
$194
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $194 found 15 hours ago
Cape Air
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 9 hours ago
$194
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $194 found 9 hours ago
JetBlue Airways
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 9 hours ago
$196
Roundtrip
found 9 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $196 found 9 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 1 day ago
$196
Roundtrip
found 1 day ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $196 found 1 day ago
Cape Air
Tue, Apr 21 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$199 Roundtrip, found 9 hours ago
$199
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Tue, Apr 21 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $199 found 9 hours ago
Cape Air
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$200 Roundtrip, found 9 hours ago
$200
Roundtrip
found 9 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $200 found 9 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 April, 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 $155, 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 $155 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$155

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 ...
8/10 Very Good! (425 reviews)
The staff were so friendly and helpful...made us feel very welcome. There was no television in our room, which was no problem...just wish we had known in advance. Then we could have brought a good book or crossword puzzle!

Reviewed on Apr 1, 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! (1,003 reviews)
Have stayed here many times. Close to town and Okemo. Very convenient.

Reviewed on Mar 30, 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! (571 reviews)
Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍

Reviewed on Apr 5, 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 (1,002 reviews)
Older motel style not fancy. Good hot tub in pool area. Ok for overnight on a budget.

Reviewed on Apr 6, 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! (1,008 reviews)
Great breakfast and excellent location.

Reviewed on Apr 5, 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! (928 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 ...
8.6/10 Excellent! (81 reviews)
Stayed in February for easy access to skiing at Mount Snow. Hideaway Inn is 2 minutes from Mount Snow and a confortable place to stay. Basic accomodations in winter but you have everything you need in a room. Beverages in common area and helpfull staff. Very pleasant check in and check out. Overall, ...

Reviewed on Apr 3, 2026

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Hideaway Inn Mt. Snow
See all 3,146 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.