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Chester

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Chester Flights as Low as $608

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

United
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$608 Roundtrip, found 1 day ago
$608
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $608 found 1 day ago
United
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$618 Roundtrip, found 1 day ago
$618
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $618 found 1 day ago
United
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$628 Roundtrip, found 2 days ago
$628
Roundtrip
found 2 days ago
Select United flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $628 found 2 days ago
United
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$633 Roundtrip, found 3 hours ago
$633
Roundtrip
found 3 hours ago
Select United flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $633 found 3 hours ago
United
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$638 Roundtrip, found 1 day ago
$638
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $638 found 1 day ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$640 Roundtrip, found 3 days ago
$640
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $640 found 3 days ago
United
Thu, Oct 1 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$643 Roundtrip, found 5 days ago
$643
Roundtrip
found 5 days ago
Select United flight, departing Thu, Oct 1 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $643 found 5 days ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$644 Roundtrip, found 3 hours ago
$644
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $644 found 3 hours ago
American Airlines
Sun, Sep 27 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$646 Roundtrip, found 5 days ago
$646
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Sep 27 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $646 found 5 days ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$649 Roundtrip, found 2 days ago
$649
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $649 found 2 days ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$651 Roundtrip, found 3 days ago
$651
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $651 found 3 days ago
American Airlines
Sun, Sep 27 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$651 Roundtrip, found 5 days ago
$651
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Sep 27 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $651 found 5 days ago
United
Sun, Sep 27 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$653 Roundtrip, found 3 days ago
$653
Roundtrip
found 3 days ago
Select United flight, departing Sun, Sep 27 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $653 found 3 days ago
JetBlue Airways
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$655 Roundtrip, found 3 hours ago
$655
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $655 found 3 hours ago
American Airlines
Sun, Sep 27 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$656 Roundtrip, found 5 days ago
$656
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Sep 27 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $656 found 5 days ago
American Airlines
Tue, Sep 29 - Wed, Oct 7
LAX
Los Angeles Intl.
LEB
Lebanon Municipal
$658 Roundtrip, found 1 day ago
$658
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 29 from Los Angeles Intl. to Lebanon Municipal, returning Wed, Oct 7, priced at $658 found 1 day 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 $608, 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 $608 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$607

Last Minute Hotel Deals in Chester

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! (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie ..."

Reviewed on Aug 30, 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! (604 reviews)
"I wouldn’t run back here. It’s a nice hotel in general. The gardens are pretty. Downsides are the facility’s. Outdoor pool area is average. Looks run down. There is no onsite indoor pool, gym, sauna etc , this is over 1 mile away and also is currently under construction. Breakfast was poor for a ..."

Reviewed on Sep 9, 2026

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Woodstock Inn & Resort
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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Latchis Hotel
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! (308 reviews)
"Pool and hot tub were closed, no fresh towels or maid service or coffee replenishment. No shuttle service available and no coffee cups provided in the lobby for complimentary coffee. The bar closed at 8:30 even though posted hours were until 10:00"

Reviewed on Sep 7, 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 ...
9.6/10 Exceptional! (314 reviews)
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."

Reviewed on Sep 6, 2026

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The Jackson
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 ...
6.6/10 (54 reviews)
"The room was dirty and smelled musty and of urine. The hallways have all broken down ice machines and the breakfast was non-existent."

Reviewed on Sep 6, 2026

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Colonial Motel
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (991 reviews)
"Lovely room for a quick stay! Staff was so kind and accommodating! 10/10 Highly recommend!"

Reviewed on Sep 7, 2026

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The Shire Woodstock
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,008 reviews)
"The inn is a little run down. The carpet in the first level hallway is in desperate need of replacement, and the downstairs hallway has a very off putting sewer smell. Lastly, the back of the inn, viewed from the expansive lawn in the back, is dirty and the railings need to be painted. On a bright ..."

Reviewed on Sep 9, 2026

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On The River Inn
See all 3,094 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.