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Chester

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Chester Flights as Low as $486

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

Delta
Mon, Nov 2 - Fri, Nov 13
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$486 Roundtrip, found 2 days ago
$486
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Fri, Nov 13, priced at $486 found 2 days ago
Delta
Tue, Oct 20 - Mon, Nov 9
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$493 Roundtrip, found 2 days ago
$493
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Mon, Nov 9, priced at $493 found 2 days ago
Delta
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$496 Roundtrip, found 2 days ago
$496
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $496 found 2 days ago
Delta
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 2 days ago
$503
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $503 found 2 days ago
Delta
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$506 Roundtrip, found 1 day ago
$506
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $506 found 1 day ago
Delta
Fri, Oct 23 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 7 hours ago
$513
Roundtrip
found 7 hours ago
Select Delta flight, departing Fri, Oct 23 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $513 found 7 hours ago
Delta
Fri, Oct 30 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$516 Roundtrip, found 2 days ago
$516
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 30 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $516 found 2 days ago
Delta
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$523 Roundtrip, found 17 hours ago
$523
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $523 found 17 hours ago
Delta
Tue, Sep 29 - Fri, Oct 2
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$523 Roundtrip, found 2 days ago
$523
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 29 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $523 found 2 days ago
Delta
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$526 Roundtrip, found 1 day ago
$526
Roundtrip
found 1 day ago
Select Delta flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $526 found 1 day ago
Delta
Tue, Oct 20 - Sat, Nov 7
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$533 Roundtrip, found 17 hours ago
$533
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Nov 7, priced at $533 found 17 hours ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$536 Roundtrip, found 1 day ago
$536
Roundtrip
found 1 day ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $536 found 1 day ago
United
Mon, Nov 2 - Wed, Nov 18
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$541 Roundtrip, found 1 day ago
$541
Roundtrip
found 1 day ago
Select United flight, departing Mon, Nov 2 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Wed, Nov 18, priced at $541 found 1 day ago
Delta
Tue, Oct 20 - Mon, Nov 9
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$543 Roundtrip, found 20 hours ago
$543
Roundtrip
found 20 hours ago
Select Delta flight, departing Tue, Oct 20 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Mon, Nov 9, priced at $543 found 20 hours ago
American Airlines
Mon, Oct 5 - Sat, Oct 17
SAT
San Antonio Intl.
RUT
Rutland Southern Vermont Regional
$546 Roundtrip, found 2 days ago
$546
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Oct 5 from San Antonio Intl. to Rutland Southern Vermont Regional, returning Sat, Oct 17, priced at $546 found 2 days ago
United
Sat, Sep 26 - Tue, Sep 29
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$606 Roundtrip, found 5 days ago
$606
Roundtrip
found 5 days ago
Select United flight, departing Sat, Sep 26 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $606 found 5 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 November, 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 $486, 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 $486 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$486

Last Minute Hotel Deals in Chester

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. ...
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Woodstock Inn & Resort
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! (970 reviews)
"The hotel was very clean and the bed quite comfy. The only downside was insufficient parking. We had to use the adjacent lot but then had to leave there by 9:00 am. We ended up having to buy time to park which wasn’t a lot of money but was a bit of an irritant. Would def stay there again!"

Reviewed on Aug 29, 2026

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Latchis Hotel
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski ...
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Grand Summit Resort, A Vail Resorts Property
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.8/10 (46 reviews)
"It was dirty. The sink, bathroom, tub, floors. All dead bugs all over. TV was great. But a very musty smell in room. My sheets were not dry when we went to bed."

Reviewed on Aug 26, 2026

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Colonial Motel
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. ...
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The Shire Woodstock
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 ...
9.2/10 Wonderful! (1,001 reviews)
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), ..."

Reviewed on Aug 29, 2026

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On The River Inn
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 a business center, a fireplace in the lobby, and laundry facilities. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (868 reviews)
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."

Reviewed on Aug 22, 2026

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG
The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
3567 Main Street Manchester VT
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
7.4/10 Good! (661 reviews)
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."

Reviewed on Aug 29, 2026

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The Equinox Golf Resort And Spa
See all 3,093 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.