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Chester

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Chester Flights as Low as $330

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

Delta
Tue, Oct 6 - Tue, Oct 13
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$330 Roundtrip, found 1 day ago
$330
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 6 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Tue, Oct 13, priced at $330 found 1 day ago
American Airlines
Tue, Oct 6 - Wed, Oct 14
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$340 Roundtrip, found 1 day ago
$340
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Oct 14, priced at $340 found 1 day ago
Delta
Sat, Oct 10 - Tue, Oct 13
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$360 Roundtrip, found 1 day ago
$360
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Oct 10 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Tue, Oct 13, priced at $360 found 1 day ago
JetBlue Airways
Tue, Oct 6 - Fri, Oct 16
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$385 Roundtrip, found 1 day ago
$385
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Lebanon Municipal, returning Fri, Oct 16, priced at $385 found 1 day ago
Delta
Sun, Oct 11 - Tue, Oct 13
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$389 Roundtrip, found 1 day ago
$389
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Oct 11 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Tue, Oct 13, priced at $389 found 1 day ago
American Airlines
Fri, Oct 9 - Wed, Oct 14
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$390 Roundtrip, found 1 day ago
$390
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 9 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Oct 14, priced at $390 found 1 day ago
Delta
Thu, Oct 8 - Thu, Oct 8
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$399 Roundtrip, found 1 day ago
$399
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Oct 8 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Thu, Oct 8, priced at $399 found 1 day ago
Delta
Tue, Oct 6 - Sat, Oct 10
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$408 Roundtrip, found 17 hours ago
$408
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 6 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Sat, Oct 10, priced at $408 found 17 hours ago
American Airlines
Tue, Oct 6 - Tue, Oct 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$408 Roundtrip, found 1 day ago
$408
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Oct 13, priced at $408 found 1 day ago
United
Sat, Oct 10 - Mon, Oct 12
IAD
Washington Dulles Intl.
LEB
Lebanon Municipal
$412 Roundtrip, found 1 day ago
$412
Roundtrip
found 1 day ago
Select United flight, departing Sat, Oct 10 from Washington Dulles Intl. to Lebanon Municipal, returning Mon, Oct 12, priced at $412 found 1 day ago
American Airlines
Tue, Oct 6 - Sun, Oct 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$415 Roundtrip, found 1 day ago
$415
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Lebanon Municipal, returning Sun, Oct 18, priced at $415 found 1 day ago
Delta
Thu, Oct 8 - Sat, Oct 10
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$418 Roundtrip, found 17 hours ago
$418
Roundtrip
found 17 hours ago
Select Delta flight, departing Thu, Oct 8 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Sat, Oct 10, priced at $418 found 17 hours ago
American Airlines
Thu, Oct 8 - Tue, Oct 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$418 Roundtrip, found 1 day ago
$418
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Oct 8 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Oct 13, priced at $418 found 1 day ago
American Airlines
Tue, Oct 6 - Fri, Oct 9
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$424 Roundtrip, found 1 day ago
$424
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 6 from Ronald Reagan Washington National to Lebanon Municipal, returning Fri, Oct 9, priced at $424 found 1 day ago
Delta
Tue, Oct 6 - Thu, Oct 15
BWI
Baltimore Washington Intl. Thurgood Marshall
LEB
Lebanon Municipal
$428 Roundtrip, found 17 hours ago
$428
Roundtrip
found 17 hours ago
Select Delta flight, departing Tue, Oct 6 from Baltimore Washington Intl. Thurgood Marshall to Lebanon Municipal, returning Thu, Oct 15, priced at $428 found 17 hours ago
JetBlue Airways
Mon, Oct 5 - Tue, Oct 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$430 Roundtrip, found 17 hours ago
$430
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Mon, Oct 5 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Oct 13, priced at $430 found 17 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 October, 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 $330, 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 $330 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$329

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! (441 reviews)
"The building was very quaint and had a historical vibe."

Reviewed on Jul 7, 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! (591 reviews)
"I am terribly sorry to give such a bad review. They put us in the basement they call ground level, the room smelled dank and like mold. Everything stayed wet..towels bathing suits. The people were nice. The elevator smelled like urin and puke..they charge a incidentale fee of 250 dollars a day that ..."

Reviewed on Jul 16, 2026

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Woodstock Inn & Resort
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd 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 ...
8.6/10 Excellent! (1,006 reviews)
"Thoughtful and attentive staff"

Reviewed on Jul 18, 2026

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Keene Elm City Hotel, an Ascend Collection 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! (854 reviews)
"The hotel was beautiful very tranquil. Lots to see and do. The staff were friendly and attentive to the guests. The food in the restaurant was amazing. The staff there were also friendly. It was so peaceful in the mountains and the hotel grounds were beautiful."

Reviewed on Jun 29, 2026

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Kimpton Taconic Hotel by IHG
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)
"when we got to the hotel after a long day of travel we found that the bar and restaurant were closed those days of the week so had to buy chips for dinner. we found a cockroach in the room and when we put out the room cleaning notice, nobody came and cleaned. when we had a nice dinner my daughter ..."

Reviewed on Jul 13, 2026

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On The River Inn
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 ...
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Best Western Plus Keene 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 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are ...
8.6/10 Excellent! (292 reviews)
"The room was clean and the facility was fine. Considering it was off season I understand the need to work on the pool and hot tub but it was still disappointing. The deli was outrageously expensive. A coffee was $6 (gas station variety) and a breakfast sandwich $16. Considering the hotel was basically ..."

Reviewed on Jul 15, 2026

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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 ...
5.8/10 (22 reviews)
"My husband and I came here for a weekend away. I hadn’t been back in the area and I guess they changed management because it was beautiful back in the day. We had to leave early due to an emergency for our son, we never spent a night there but when I asked if we could be refunded for our second night ..."

Reviewed on Jul 17, 2026

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Colonial Motel
See all 3,087 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.