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Chester

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Chester Flights as Low as $459

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

JetBlue Airways
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$459 Roundtrip, found 4 days ago
$459
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $459 found 4 days ago
Delta
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$465 Roundtrip, found 4 days ago
$465
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $465 found 4 days ago
Delta
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$470 Roundtrip, found 4 days ago
$470
Roundtrip
found 4 days ago
Select Delta flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $470 found 4 days ago
JetBlue Airways
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$474 Roundtrip, found 4 days ago
$474
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $474 found 4 days ago
United
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$474 Roundtrip, found 4 days ago
$474
Roundtrip
found 4 days ago
Select United flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $474 found 4 days ago
JetBlue Airways
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$485 Roundtrip, found 4 days ago
$485
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $485 found 4 days ago
American Airlines
Thu, Mar 19 - Mon, Mar 23
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$490 Roundtrip, found 4 days ago
$490
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 23, priced at $490 found 4 days ago
JetBlue Airways
Thu, Mar 19 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$500 Roundtrip, found 16 hours ago
$500
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $500 found 16 hours ago
JetBlue Airways
Thu, Mar 19 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$505 Roundtrip, found 16 hours ago
$505
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $505 found 16 hours ago
American Airlines
Thu, Mar 19 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$510 Roundtrip, found 16 hours ago
$510
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $510 found 16 hours ago
JetBlue Airways
Thu, Mar 19 - Wed, Apr 1
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$510 Roundtrip, found 1 day ago
$510
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Apr 1, priced at $510 found 1 day ago
American Airlines
Wed, Mar 18 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$513 Roundtrip, just found
$513
Roundtrip
just found
Select American Airlines flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $513 just found
JetBlue Airways
Thu, Mar 19 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$514 Roundtrip, found 16 hours ago
$514
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $514 found 16 hours ago
JetBlue Airways
Thu, Mar 19 - Mon, Mar 30
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$515 Roundtrip, found 12 hours ago
$515
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Mon, Mar 30, priced at $515 found 12 hours ago
JetBlue Airways
Thu, Mar 19 - Tue, Mar 31
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$520 Roundtrip, found 16 hours ago
$520
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 31, priced at $520 found 16 hours ago
United
Fri, Mar 27 - Wed, Apr 1
MLI
Quad City Intl.
LEB
Lebanon Municipal
$561 Roundtrip, found 4 days ago
$561
Roundtrip
found 4 days ago
Select United flight, departing Fri, Mar 27 from Quad City Intl. to Lebanon Municipal, returning Wed, Apr 1, priced at $561 found 4 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 March, 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 $459, 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 $459 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$180

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! (422 reviews)
Gorgeous old Inn that is fairly well maintained to keep up with modern competition. We visited in the dead of winter so the quaint town of Chester, VT didn’t have a lot to offer. We plan on visiting again in the summer to get the full experience!

Reviewed on Mar 10, 2026

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Fullerton Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,004 reviews)
Staff is incredibly friendly and helpful. Rooms are okay. Pool and Tub fine but crowded

Reviewed on Mar 15, 2026

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Pointe at Castle Hill Resort
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. ...
9.2/10 Wonderful! (567 reviews)
Amazing restaurant and attentive staff

Reviewed on Mar 4, 2026

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Woodstock Inn & Resort
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are ...
8.8/10 Excellent! (72 reviews)
This place is a hidden gem! It looks very unassuming from the outside but inside was gorgeous and cozy. It looks newly updated/renovated, with a modern cabin feel. The room was big and spacious and even had a real record player which my husband and kids could not get enough of. Easy check in and ...

Reviewed on Mar 14, 2026

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Hideaway Inn Mt. Snow
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St 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 breakfast and the ...
9.6/10 Exceptional! (1,008 reviews)
Great hotel , friendly staff, clean and breakfast was gr

Reviewed on Mar 16, 2026

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Hampton Inn and Suites Manchester
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (914 reviews)
yes

Reviewed on Mar 15, 2026

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The Palmer House Resort, an Ascend Collection Hotel
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A 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! (604 reviews)
Hot tub nor sauna we’re working. This is pretty important for a ski Hotel, or anyone that bills themselves as a spa.

Reviewed on Mar 11, 2026

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The Equinox Golf Resort & 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 resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (812 reviews)
Road surface in parking lot when exiting car was icy

Reviewed on Mar 12, 2026

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 3,128 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.