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Chester

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Chester Flights as Low as $349

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

JetBlue Airways
Wed, Jun 25 - Sat, Jun 28
RIC
Richmond Intl.
LEB
Lebanon Municipal
$349 Roundtrip, found 3 days ago
$349
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Sat, Jun 28, priced at $349 found 3 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$400 Roundtrip, found 3 days ago
$400
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $400 found 3 days ago
JetBlue Airways
Thu, Jun 26 - Fri, Jul 4
RIC
Richmond Intl.
LEB
Lebanon Municipal
$405 Roundtrip, found 2 days ago
$405
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Fri, Jul 4, priced at $405 found 2 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$410 Roundtrip, found 3 days ago
$410
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $410 found 3 days ago
JetBlue Airways
Fri, Jun 27 - Tue, Jul 1
RIC
Richmond Intl.
LEB
Lebanon Municipal
$413 Roundtrip, found 3 days ago
$413
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Jun 27 from Richmond Intl. to Lebanon Municipal, returning Tue, Jul 1, priced at $413 found 3 days ago
JetBlue Airways
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $415 found 3 days ago
American Airlines
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$420 Roundtrip, found 3 days ago
$420
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $420 found 3 days ago
JetBlue Airways
Fri, Jun 27 - Sat, Jun 28
RIC
Richmond Intl.
LEB
Lebanon Municipal
$423 Roundtrip, found 3 days ago
$423
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Fri, Jun 27 from Richmond Intl. to Lebanon Municipal, returning Sat, Jun 28, priced at $423 found 3 days ago
Delta
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$430 Roundtrip, found 3 days ago
$430
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $430 found 3 days ago
JetBlue Airways
Sun, Jun 29 - Wed, Jul 2
RIC
Richmond Intl.
LEB
Lebanon Municipal
$433 Roundtrip, found 1 day ago
$433
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, Jun 29 from Richmond Intl. to Lebanon Municipal, returning Wed, Jul 2, priced at $433 found 1 day ago
JetBlue Airways
Thu, Jun 26 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$435 Roundtrip, found 3 days ago
$435
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $435 found 3 days ago
American Airlines
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$437 Roundtrip, found 3 days ago
$437
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $437 found 3 days ago
Delta
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$437 Roundtrip, found 3 days ago
$437
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $437 found 3 days ago
JetBlue Airways
Thu, Jun 26 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Jun 26 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $441 found 3 days ago
JetBlue Airways
Tue, Jun 24 - Sat, Jun 28
RIC
Richmond Intl.
LEB
Lebanon Municipal
$441 Roundtrip, found 3 days ago
$441
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Jun 24 from Richmond Intl. to Lebanon Municipal, returning Sat, Jun 28, priced at $441 found 3 days ago
American Airlines
Wed, Jun 25 - Mon, Jun 30
RIC
Richmond Intl.
LEB
Lebanon Municipal
$442 Roundtrip, found 3 days ago
$442
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Jun 25 from Richmond Intl. to Lebanon Municipal, returning Mon, Jun 30, priced at $442 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 June, 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 $349, 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 $349 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$348

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! (355 reviews)
"We enjoyed our stay at this lovely Inn, it was quiet and the owner was welcoming and knowledgeable about the area. Our youngest especially enjoyed the checkerboard in the lounge"

Reviewed on Jun 9, 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! (519 reviews)
Stunning
"Always a stunning stay in Woodstock!"

Reviewed on Jun 2, 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! (482 reviews)
"The facility is lovely. As much as the coffee set up near the lobby was good it is still better to have one in the room when you first wake up. The TV reception could be improved if possible. Watching Ladies golf tournament and when the 18th hole deciding game it lost connection, other than that ..."

Reviewed on Jun 5, 2025

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The Equinox Golf Resort & Spa
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 ...
6.8/10 (1,001 reviews)
"Fabulous and clean for an affordable price"

Reviewed on May 27, 2025

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Colonial Motel And 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! (757 reviews)
"property was great , small grocery store across the street very convenient. Everything in walking distance. Only negative was we arrived on a monday and most restaurants are closed."

Reviewed on Jun 13, 2025

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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 ...
8/10 Very Good! (833 reviews)
"So far so good. We definitely coming back again in the future."

Reviewed on Jun 8, 2025

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Hampton Inn Brattleboro
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (639 reviews)
"Staff was very helpful and easy access to the interstate."

Reviewed on Jun 9, 2025

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Comfort Inn & Suites Brattleboro I-91
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! (772 reviews)
"Absolutely Beautiful property."

Reviewed on Jun 9, 2025

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Kimpton Taconic Hotel by IHG
See all 2,981 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.