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Chester

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Chester Flights as Low as $342

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

Delta
Wed, Mar 18 - Wed, Mar 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$342 Roundtrip, found 3 hours ago
$342
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 18, priced at $342 found 3 hours ago
Delta
Wed, Mar 18 - Sat, Mar 28
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$345 Roundtrip, found 2 hours ago
$345
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Mar 28, priced at $345 found 2 hours ago
Delta
Tue, Mar 17 - Tue, Mar 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$346 Roundtrip, found 3 hours ago
$346
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Mar 17 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 17, priced at $346 found 3 hours ago
Delta
Thu, Mar 19 - Sat, Mar 28
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$347 Roundtrip, found 2 hours ago
$347
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Mar 28, priced at $347 found 2 hours ago
Delta
Wed, Mar 18 - Fri, Mar 27
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$348 Roundtrip, found 2 hours ago
$348
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Fri, Mar 27, priced at $348 found 2 hours ago
Delta
Tue, Mar 17 - Sat, Mar 28
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$348 Roundtrip, found 2 hours ago
$348
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Mar 17 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Mar 28, priced at $348 found 2 hours ago
Delta
Thu, Mar 19 - Fri, Mar 27
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$350 Roundtrip, found 2 hours ago
$350
Roundtrip
found 2 hours ago
Select Delta flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Fri, Mar 27, priced at $350 found 2 hours ago
Delta
Wed, Mar 18 - Wed, Mar 25
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$351 Roundtrip, found 3 hours ago
$351
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 25, priced at $351 found 3 hours ago
American Airlines
Thu, Mar 19 - Wed, Mar 25
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$353 Roundtrip, found 2 hours ago
$353
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Thu, Mar 19 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 25, priced at $353 found 2 hours ago
JetBlue Airways
Wed, Mar 18 - Wed, Mar 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$354 Roundtrip, found 3 hours ago
$354
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 18, priced at $354 found 3 hours ago
Delta
Tue, Mar 17 - Wed, Mar 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$355 Roundtrip, found 2 hours ago
$355
Roundtrip
found 2 hours ago
Select Delta flight, departing Tue, Mar 17 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 18, priced at $355 found 2 hours ago
Delta
Mon, Mar 16 - Sat, Mar 28
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$355 Roundtrip, found 2 hours ago
$355
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Mar 16 from Ronald Reagan Washington National to Lebanon Municipal, returning Sat, Mar 28, priced at $355 found 2 hours ago
Delta
Wed, Mar 18 - Wed, Mar 25
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$357 Roundtrip, found 3 hours ago
$357
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 25, priced at $357 found 3 hours ago
JetBlue Airways
Tue, Mar 17 - Tue, Mar 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$357 Roundtrip, found 3 hours ago
$357
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Mar 17 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 17, priced at $357 found 3 hours ago
Delta
Mon, Mar 16 - Tue, Mar 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$358 Roundtrip, found 1 hour ago
$358
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Mar 16 from Ronald Reagan Washington National to Lebanon Municipal, returning Tue, Mar 17, priced at $358 found 1 hour ago
JetBlue Airways
Wed, Mar 18 - Wed, Mar 18
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$359 Roundtrip, found 3 hours ago
$359
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Wed, Mar 18 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Mar 18, priced at $359 found 3 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 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 $342, 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 $342 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$342

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! (420 reviews)
The hotel bed sinks . My partner and I woke up with terrible stiffness and back pain. We could not sta another night there ( we booked 3 nights ) and stayed at another hotel for one night. The bed was so uncomfortable that we decided to end our trip a day early rather than stay there. Overall the ...

Reviewed on Feb 24, 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! (994 reviews)
Service was good. the people at the front desk are very nice. the photos are misleading for the booking I thought I would have a kitchen but I showed up with trays of food and not even a microwave. only a mini fridge. For these prices they gotta be better than that.

Reviewed on Feb 27, 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! (565 reviews)
Very clean, high end, friendly staff

Reviewed on Feb 20, 2026

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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
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! (598 reviews)
Beautiful hotel. Nice pool and gym.

Reviewed on Feb 19, 2026

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The Equinox Golf Resort & Spa
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! (905 reviews)
Save your money and stay next door

Reviewed on Feb 28, 2026

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The Palmer House Resort, an Ascend Collection Hotel
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! (1,001 reviews)
Great

Reviewed on Feb 23, 2026

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Hampton Inn and Suites Manchester
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! (833 reviews)
Hotel was lovely. Beautifully appointed. Staff was excellent and very helpful.

Reviewed on Feb 27, 2026

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Kimpton Taconic Hotel by IHG
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! (805 reviews)
Courteous staff. Clean rooms.

Reviewed on Feb 23, 2026

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 3,131 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.