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Chester

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Chester Flights as Low as $476

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

JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$476 Roundtrip, found 5 hours ago
$476
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $476 found 5 hours ago
United
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$479 Roundtrip, found 12 hours ago
$479
Roundtrip
found 12 hours ago
Select United flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $479 found 12 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$486 Roundtrip, found 5 hours ago
$486
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $486 found 5 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$489 Roundtrip, found 12 hours ago
$489
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $489 found 12 hours ago
JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 4 hours ago
$492
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $492 found 4 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$497 Roundtrip, found 12 hours ago
$497
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $497 found 12 hours ago
American Airlines
Tue, Aug 4 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$499 Roundtrip, found 1 day ago
$499
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 4 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $499 found 1 day ago
JetBlue Airways
Wed, Sep 23 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 4 hours ago
$502
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $502 found 4 hours ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 4 hours ago
$503
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $503 found 4 hours ago
JetBlue Airways
Fri, Jul 17 - Thu, Jul 23
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 4 hours ago
$504
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Fri, Jul 17 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at $504 found 4 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$505 Roundtrip, found 5 hours ago
$505
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $505 found 5 hours ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DEN
Denver Intl.
LEB
Lebanon Municipal
$507 Roundtrip, found 12 hours ago
$507
Roundtrip
found 12 hours ago
Select American Airlines flight, departing Tue, Oct 6 from Denver Intl. to Lebanon Municipal, returning Wed, Oct 14, priced at $507 found 12 hours ago
American Airlines
Sat, Aug 1 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 1 day ago
$507
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 1 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $507 found 1 day ago
United
Fri, Sep 25 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$508 Roundtrip, found 12 hours ago
$508
Roundtrip
found 12 hours ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $508 found 12 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 5 hours ago
$511
Roundtrip
found 5 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $511 found 5 hours ago
United
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$578 Roundtrip, found 3 days ago
$578
Roundtrip
found 3 days ago
Select United flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $578 found 3 days 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 July, 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 $476, 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 $476 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$475

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! (439 reviews)
"We had a wonderful weekend. Inn is a little dated but very cute. Room was clean and we sat out on our balcony with wine at night and coffee in the morning. Needed a dusting but comfortable. I would stay there again and recommend it to those traveling. Great location."

Reviewed on Jun 21, 2026

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Fullerton Inn
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! (588 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

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Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,000 reviews)
"It was beautiful, well designed with plenty of public gathering and relaxing places. The restaurant was excellent for both dinner and breakfast. We loved the coffee bars open all day. Great staff who were very professional and friendly!"

Reviewed on Jun 24, 2026

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On The River Inn
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (911 reviews)
"Enjoyed our one night stay. Convenient location. Unique vibe. Staff very helpful and friendly."

Reviewed on Jun 26, 2026

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Latchis Hotel
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. ...
9.4/10 Exceptional! (852 reviews)
"The lobby and rooms were well maintained and clean. Daytime hotel staff was professional and friendly. Nighttime staff, although may have been doing his job, was curt when inquired about the bar (closed) and fire pit access (“if it’s on. Otherwise, I don’t have the key for it.” A bunch of us sat ..."

Reviewed on Jun 26, 2026

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Kimpton Taconic Hotel by IHG
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,005 reviews)
"Everything was great except that the room's bathroom floor was still wet, presumably from the previous occupant."

Reviewed on Jun 25, 2026

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Best Western Plus Keene Hotel
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (949 reviews)
"Walkable to downtown Woodstock. Loved our room with balcony over looking the river."

Reviewed on Jun 27, 2026

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The Shire Woodstock
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8.2/10 Very Good! (1,001 reviews)
"The staff were very professional. Hotel was clean and very nice"

Reviewed on Jun 27, 2026

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Hampton Inn Brattleboro
See all 3,103 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.