Search Cheap Flights to
Chester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chester Flights as Low as $399

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

JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$399 Roundtrip, found 11 hours ago
$399
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $399 found 11 hours ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$409 Roundtrip, found 11 hours ago
$409
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $409 found 11 hours ago
Delta
Tue, Nov 17 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$419 Roundtrip, found 5 days ago
$419
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $419 found 5 days ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$419 Roundtrip, found 11 hours ago
$419
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $419 found 11 hours ago
Delta
Wed, Nov 18 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$429 Roundtrip, found 5 days ago
$429
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $429 found 5 days ago
Delta
Wed, Nov 18 - Tue, Dec 1
MIA
Miami Intl.
LEB
Lebanon Municipal
$440 Roundtrip, found 5 days ago
$440
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $440 found 5 days ago
American Airlines
Wed, Nov 18 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$450 Roundtrip, found 3 hours ago
$450
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $450 found 3 hours ago
American Airlines
Wed, Nov 18 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$460 Roundtrip, found 3 hours ago
$460
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $460 found 3 hours ago
American Airlines
Wed, Nov 18 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$470 Roundtrip, found 3 hours ago
$470
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $470 found 3 hours ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$474 Roundtrip, just found
$474
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $474 just found
Delta
Tue, Nov 17 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$479 Roundtrip, found 5 days ago
$479
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $479 found 5 days ago
United
Tue, Nov 17 - Wed, Dec 2
MIA
Miami Intl.
LEB
Lebanon Municipal
$481 Roundtrip, found 2 hours ago
$481
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Nov 17 from Miami Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $481 found 2 hours ago
JetBlue Airways
Wed, Nov 18 - Tue, Dec 1
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$484 Roundtrip, just found
$484
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Nov 18 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Tue, Dec 1, priced at $484 just found
United
Wed, Nov 18 - Thu, Dec 3
MIA
Miami Intl.
LEB
Lebanon Municipal
$485 Roundtrip, found 3 hours ago
$485
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Nov 18 from Miami Intl. to Lebanon Municipal, returning Thu, Dec 3, priced at $485 found 3 hours ago
JetBlue Airways
Tue, Nov 17 - Wed, Dec 2
FLL
Fort Lauderdale - Hollywood Intl.
LEB
Lebanon Municipal
$495 Roundtrip, found 11 hours ago
$495
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Nov 17 from Fort Lauderdale - Hollywood Intl. to Lebanon Municipal, returning Wed, Dec 2, priced at $495 found 11 hours ago
American Airlines
Mon, Oct 19 - Tue, Oct 20
SEA
Seattle - Tacoma Intl.
LEB
Lebanon Municipal
$755 Roundtrip, found 1 day ago
$755
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Oct 19 from Seattle - Tacoma Intl. to Lebanon Municipal, returning Tue, Oct 20, priced at $755 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 November, 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 $399, 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 $399 right now, why wait?

Chester Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$479

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 ...
Get rates
Fullerton Inn
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! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."

Reviewed on Oct 8, 2026

Get rates
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! (617 reviews)
"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."

Reviewed on Oct 11, 2026

Get rates
Woodstock Inn & Resort
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 ...
Get rates
Grand Summit Resort, A Vail Resorts Property
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
5669 Main Street Manchester Center VT
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (700 reviews)
"This was the first time I've ever stayed in a hotel where you arrive and go straight to your room without having to check in at a front desk first. The instructions via email or text (whichever it was) for how to do so were clear and we had no problems getting into our room. The location was convenient ..."

Reviewed on Oct 11, 2026

Get rates
Aspen At Manchester
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A 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 helpful staff and ...
9.4/10 Exceptional! (925 reviews)
"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked ..."

Reviewed on Oct 10, 2026

Get rates
The Manchester View
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 ...
6.2/10 (88 reviews)
"The room smelled unpleasant and the tub was fairly mildewy."

Reviewed on Oct 12, 2026

Get rates
Colonial Motel
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Book a stay at this ski hotel in Ludlow. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the property condition in ...
8.6/10 Excellent! (925 reviews)
"Bed was a very uncomfortable Murphy bed which was not disclosed when booking. Property and room did not feel clean. Property amenities were nice and in a convenient location."

Reviewed on Oct 12, 2026

Get rates
Jackson Gore Village, A Vail Resorts Property
See all 3,116 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.