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Chester

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Chester Flights as Low as $474

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

JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$474 Roundtrip, just found
$474
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $474 just found
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$484 Roundtrip, just found
$484
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $484 just found
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, just found
$495
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $495 just found
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, just found
$495
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $495 just found
Delta
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$505 Roundtrip, just found
$505
Roundtrip
just found
Select Delta flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $505 just found
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$506 Roundtrip, just found
$506
Roundtrip
just found
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $506 just found
American Airlines
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$510 Roundtrip, just found
$510
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $510 just found
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$511 Roundtrip, found 3 days ago
$511
Roundtrip
found 3 days ago
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $511 found 3 days ago
Delta
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$515 Roundtrip, just found
$515
Roundtrip
just found
Select Delta flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $515 just found
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$515 Roundtrip, found 4 days ago
$515
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $515 found 4 days ago
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$516 Roundtrip, just found
$516
Roundtrip
just found
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $516 just found
American Airlines
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$520 Roundtrip, just found
$520
Roundtrip
just found
Select American Airlines flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $520 just found
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$521 Roundtrip, found 3 days ago
$521
Roundtrip
found 3 days ago
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $521 found 3 days ago
Delta
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$525 Roundtrip, just found
$525
Roundtrip
just found
Select Delta flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $525 just found
United
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$526 Roundtrip, just found
$526
Roundtrip
just found
Select United flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $526 just found
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$530 Roundtrip, found 11 hours ago
$530
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $530 found 11 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 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 $474, 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 $474 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$479

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 ...
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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! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."

Reviewed on Oct 8, 2026

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Stone Hearth Inn and Eatery
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! (617 reviews)
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."

Reviewed on Oct 11, 2026

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Woodstock Inn & Resort
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
5669 Main Street Manchester Center VT
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (700 reviews)
"This was the first time I've ever stayed in a hotel where you arrive and go straight to your room without having to check in at a front desk first. The instructions via email or text (whichever it was) for how to do so were clear and we had no problems getting into our room. The location was convenient ..."

Reviewed on Oct 11, 2026

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Aspen At Manchester
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 ...
6.2/10 (87 reviews)
"No hot water, and it was a known problem. They ran out of fuel for hot water heater. Couldn’t have cared less!"

Reviewed on Oct 10, 2026

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Colonial Motel
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 ...
8.6/10 Excellent! (314 reviews)
"Allen in the restaurant is great."

Reviewed on Oct 6, 2026

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Grand Summit Resort, A Vail Resorts Property
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions ...
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The Jackson
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A 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 helpful staff and ...
9.4/10 Exceptional! (925 reviews)
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked ..."

Reviewed on Oct 10, 2026

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The Manchester View
See all 3,116 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.