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Chester

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Chester Flights as Low as $295

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

JetBlue Airways
Wed, Sep 10 - Wed, Sep 17
TPA
Tampa Intl.
LEB
Lebanon Municipal
$295 Roundtrip, found 2 days ago
$295
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $295 found 2 days ago
JetBlue Airways
Tue, Sep 9 - Wed, Sep 17
TPA
Tampa Intl.
LEB
Lebanon Municipal
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $300 found 2 days ago
JetBlue Airways
Wed, Sep 10 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$305 Roundtrip, found 2 days ago
$305
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $305 found 2 days ago
JetBlue Airways
Mon, Sep 8 - Wed, Sep 17
TPA
Tampa Intl.
LEB
Lebanon Municipal
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $310 found 2 days ago
JetBlue Airways
Tue, Sep 16 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$322 Roundtrip, found 2 days ago
$322
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Lebanon Municipal, returning Thu, Sep 18, priced at $322 found 2 days ago
JetBlue Airways
Wed, Sep 10 - Wed, Sep 17
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$324 Roundtrip, found 4 days ago
$324
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 17, priced at $324 found 4 days ago
JetBlue Airways
Tue, Sep 9 - Fri, Sep 19
TPA
Tampa Intl.
LEB
Lebanon Municipal
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 19, priced at $327 found 2 days ago
JetBlue Airways
Thu, Sep 11 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$330 Roundtrip, found 2 days ago
$330
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Sep 11 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $330 found 2 days ago
JetBlue Airways
Wed, Sep 10 - Thu, Sep 18
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$334 Roundtrip, found 4 days ago
$334
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Rutland Southern Vermont Regional, returning Thu, Sep 18, priced at $334 found 4 days ago
JetBlue Airways
Mon, Sep 8 - Fri, Sep 19
TPA
Tampa Intl.
LEB
Lebanon Municipal
$337 Roundtrip, found 2 days ago
$337
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 19, priced at $337 found 2 days ago
JetBlue Airways
Tue, Sep 16 - Wed, Sep 24
TPA
Tampa Intl.
LEB
Lebanon Municipal
$341 Roundtrip, found 2 days ago
$341
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 24, priced at $341 found 2 days ago
JetBlue Airways
Wed, Sep 10 - Mon, Sep 15
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$344 Roundtrip, found 4 days ago
$344
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Rutland Southern Vermont Regional, returning Mon, Sep 15, priced at $344 found 4 days ago
JetBlue Airways
Wed, Sep 10 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 1 day ago
$345
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $345 found 1 day ago
JetBlue Airways
Wed, Sep 17 - Thu, Sep 18
TPA
Tampa Intl.
LEB
Lebanon Municipal
$349 Roundtrip, found 2 days ago
$349
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Sep 17 from Tampa Intl. to Lebanon Municipal, returning Thu, Sep 18, priced at $349 found 2 days ago
JetBlue Airways
Tue, Sep 9 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$350 Roundtrip, found 2 days ago
$350
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $350 found 2 days ago
Delta
Thu, Sep 4 - Sat, Sep 13
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$363 Roundtrip, found 23 hours ago
$363
Roundtrip
found 23 hours ago
Select Delta flight, departing Thu, Sep 4 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Sep 13, priced at $363 found 23 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 September, 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 $295, 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 $295 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$295

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 ...
8/10 Very Good! (370 reviews)
Great Inn in a quaint town.
"A wonderful little Inn with such a pleasant owner and just a great vibe there. Would absolutely recommend for a summer or winter stay. Can imagine it is beautiful in the winter."

Reviewed on Aug 3, 2025

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Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (530 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

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Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (505 reviews)
"My husband and I stayed one night to celebrate our anniversary. The room was clean, roomy and comfortable. The hotel is huge in a beautiful surrounding with many activities included in the price. Swimming, bike riding and an easy drive into the main town. We would recommend the Equinox and plan on ..."

Reviewed on Aug 6, 2025

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The Equinox Golf Resort & Spa
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (796 reviews)
"Beautiful pet friendly place in the heart of Woodstock Village. Scenery is lovely, soothing and plenty to do. Can walk to things, bike or hike."

Reviewed on Aug 1, 2025

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The Shire Woodstock
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.6/10 (1,000 reviews)
"Always a pleasure to stay at the Colonial"

Reviewed on Jul 28, 2025

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Colonial Motel And Spa
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 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our ...
8.8/10 Excellent! (729 reviews)
"Very spacious"

Reviewed on Aug 8, 2025

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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
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (782 reviews)
"Great location, nice front porch. Nice bar. There is no gym, breakfast, snacks, or gift shop, however, a clothing boutique is available. As a pet-friendly hotel, oftentimes I was interrupted by dogs barking and growling at each other - I felt I was at a kennel. Value for the room rate was ..."

Reviewed on Jul 24, 2025

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Kimpton Taconic Hotel by IHG
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 ...
8/10 Very Good! (859 reviews)
"this is a very nice hotel, and we have stayed before and will stay again, but we will never stay in 212 again, they play music in the lobby and halls 24/7 which is fine, but 212 is right over the lobby and you can hear the drumming all night, it is very irritating, but like I said we have stayed ..."

Reviewed on Aug 4, 2025

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Hampton Inn Brattleboro
See all 2,972 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.