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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
Mon, May 25 - Sun, Jun 14
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$134 Roundtrip, found 1 hour ago
$134
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, May 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at $134 found 1 hour ago
JetBlue Airways
Sat, May 30 - Sun, Jun 14
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 1 hour ago
$163
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at $163 found 1 hour ago
JetBlue Airways
Mon, May 25 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 1 hour ago
$167
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Mon, May 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $167 found 1 hour ago
JetBlue Airways
Mon, May 4 - Wed, May 20
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$174 Roundtrip, found 23 hours ago
$174
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 20, priced at $174 found 23 hours ago
JetBlue Airways
Wed, May 27 - Sun, Jun 14
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Wed, May 27 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at $178 found 1 hour ago
Cape Air
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 1 hour ago
$180
Roundtrip
found 1 hour 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 1 hour ago
JetBlue Airways
Sat, Apr 25 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 5 hours ago
$184
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Apr 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $184 found 5 hours ago
Cape Air
Tue, May 26 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Tue, May 26 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $184 found 1 hour ago
Cape Air
Sat, May 30 - Sun, Jun 14
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 1 hour ago
$186
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at $186 found 1 hour ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 11 hours ago
$188
Roundtrip
found 11 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 11 hours ago
JetBlue Airways
Sat, Apr 25 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 5 hours ago
$189
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Sat, Apr 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $189 found 5 hours ago
Cape Air
Sat, May 30 - Sat, Jun 13
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 11 hours ago
$190
Roundtrip
found 11 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, Jun 13, priced at $190 found 11 hours ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $193 found 11 hours ago
Cape Air
Fri, May 29 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 1 hour ago
$194
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Fri, May 29 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $194 found 1 hour ago
JetBlue Airways
Sat, May 30 - Sun, Jun 14
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 1 hour ago
$196
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 14, priced at $196 found 1 hour ago
JetBlue Airways
Tue, Aug 25 - Tue, Sep 1
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$438 Roundtrip, found 1 day ago
$438
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Denver Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 1, priced at $438 found 1 day 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! (431 reviews)
The staff were incredible and the property have the perfect vibes for a ski trip. The food was great and everything was very clean and comfy.

Reviewed on Apr 16, 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! (1,002 reviews)
Super kind staff members. Our family arrived early, and they were able to find a room for us within an hour. Pool is clean as well!

Reviewed on Apr 15, 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
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
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! (1,001 reviews)
Nice stay! Staff was very accommodating.

Reviewed on Apr 17, 2026

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Hampton Inn and Suites Manchester
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
Stay at this resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (825 reviews)
Staff were super friendly. Miles was great to deal with. Amazing gentleman and very friendly and helpful. Others were also equally helpful. Loved it!

Reviewed on Apr 9, 2026

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
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Kimpton Taconic Hotel by IHG
See all 3,079 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.