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 $315

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

JetBlue Airways
Wed, Sep 10 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$315 Roundtrip, found 4 days ago
$315
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $315 found 4 days ago
JetBlue Airways
Tue, Sep 9 - Sat, Sep 13
TPA
Tampa Intl.
LEB
Lebanon Municipal
$320 Roundtrip, found 4 days ago
$320
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, Sep 9 from Tampa Intl. to Lebanon Municipal, returning Sat, Sep 13, priced at $320 found 4 days ago
American Airlines
Mon, Sep 1 - Wed, Sep 10
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$335 Roundtrip, found 6 days ago
$335
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 1 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Sep 10, priced at $335 found 6 days ago
American Airlines
Wed, Sep 10 - Wed, Sep 17
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$337 Roundtrip, found 6 days ago
$337
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Sep 10 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Sep 17, priced at $337 found 6 days ago
JetBlue Airways
Tue, Sep 16 - Tue, Sep 23
TPA
Tampa Intl.
LEB
Lebanon Municipal
$340 Roundtrip, found 3 days ago
$340
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Tue, Sep 16 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 23, priced at $340 found 3 days ago
American Airlines
Mon, Sep 1 - Wed, Sep 10
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$345 Roundtrip, found 6 days ago
$345
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 1 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Sep 10, priced at $345 found 6 days ago
JetBlue Airways
Wed, Sep 10 - Mon, Sep 15
TPA
Tampa Intl.
LEB
Lebanon Municipal
$345 Roundtrip, found 10 hours ago
$345
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Mon, Sep 15, priced at $345 found 10 hours ago
American Airlines
Wed, Sep 10 - Wed, Sep 17
MIA
Miami Intl.
LEB
Lebanon Municipal
$346 Roundtrip, found 21 hours ago
$346
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Wed, Sep 10 from Miami Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $346 found 21 hours ago
JetBlue Airways
Sat, Sep 6 - Wed, Sep 10
TPA
Tampa Intl.
LEB
Lebanon Municipal
$346 Roundtrip, found 10 hours ago
$346
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sat, Sep 6 from Tampa Intl. to Lebanon Municipal, returning Wed, Sep 10, priced at $346 found 10 hours ago
JetBlue Airways
Sat, Sep 13 - Tue, Sep 23
TPA
Tampa Intl.
LEB
Lebanon Municipal
$350 Roundtrip, found 3 days ago
$350
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Sep 13 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 23, priced at $350 found 3 days ago
JetBlue Airways
Wed, Sep 10 - Fri, Sep 12
TPA
Tampa Intl.
LEB
Lebanon Municipal
$355 Roundtrip, found 10 hours ago
$355
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Wed, Sep 10 from Tampa Intl. to Lebanon Municipal, returning Fri, Sep 12, priced at $355 found 10 hours ago
JetBlue Airways
Mon, Sep 8 - Tue, Sep 16
TPA
Tampa Intl.
LEB
Lebanon Municipal
$356 Roundtrip, found 10 hours ago
$356
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Mon, Sep 8 from Tampa Intl. to Lebanon Municipal, returning Tue, Sep 16, priced at $356 found 10 hours ago
American Airlines
Mon, Sep 1 - Wed, Sep 10
DCA
Ronald Reagan Washington National
LEB
Lebanon Municipal
$359 Roundtrip, found 6 days ago
$359
Roundtrip
found 6 days ago
Select American Airlines flight, departing Mon, Sep 1 from Ronald Reagan Washington National to Lebanon Municipal, returning Wed, Sep 10, priced at $359 found 6 days ago
American Airlines
Sat, Sep 13 - Wed, Sep 17
MIA
Miami Intl.
LEB
Lebanon Municipal
$361 Roundtrip, found 21 hours ago
$361
Roundtrip
found 21 hours ago
Select American Airlines flight, departing Sat, Sep 13 from Miami Intl. to Lebanon Municipal, returning Wed, Sep 17, priced at $361 found 21 hours ago
JetBlue Airways
Mon, Sep 15 - Sat, Sep 20
TPA
Tampa Intl.
RUT
Rutland Southern Vermont Regional
$381 Roundtrip, found 1 day ago
$381
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 15 from Tampa Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 20, priced at $381 found 1 day ago
American Airlines
Wed, Sep 17 - Fri, Oct 24
AUS
Austin-Bergstrom Intl.
LEB
Lebanon Municipal
$476 Roundtrip, found 11 hours ago
$476
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Sep 17 from Austin-Bergstrom Intl. to Lebanon Municipal, returning Fri, Oct 24, priced at $476 found 11 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 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 $315, 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 $315 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$314

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! (369 reviews)
"It’s not like anyplace I have stayed before. It’s so homey and very comfortable. The staff is very friendly and it’s clean as a whistle."

Reviewed on Jul 25, 2025

Get rates
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! (528 reviews)
"Really enjoyed our stay."

Reviewed on Jul 18, 2025

Get rates
Woodstock Inn & Resort
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 ...
6.6/10 (1,009 reviews)
"Location, quiet, suite amenities and size"

Reviewed on Jul 27, 2025

Get rates
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! (789 reviews)
"Decent, clean accommodations. Close to downtown. Nice views. Staff were very helpful and worked with our changing plans. Rooms on the lowest level of the River building had a good deal of moisture build-up (like a basement), so things /felt/ a little damp (nice river access, though). One room had ..."

Reviewed on Jul 28, 2025

Get rates
The Shire Woodstock
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! (780 reviews)
"Great location, nice front porch. Nice bar. There is no gym, breakfast, snacks, or gift shop, however, a clothing boutique is available. As a pet-friendly hotel, oftentimes I was interrupted by dogs barking and growling at each other - I felt I was at a kennel. Value for the room rate was ..."

Reviewed on Jul 24, 2025

Get rates
Kimpton Taconic Hotel by IHG
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 ...
7.4/10 Good! (500 reviews)
"Beautiful setting! Comfortable rooms"

Reviewed on Jul 25, 2025

Get rates
The Equinox Golf Resort & Spa
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! (854 reviews)
"The peoplw were nice The room was clean For the price upgrades are needed"

Reviewed on Jul 20, 2025

Get rates
Hampton Inn Brattleboro
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. ...
8.4/10 Very Good! (765 reviews)
"The parking lot is not big enough to accommodate cars."

Reviewed on Jul 27, 2025

Get rates
Latchis Hotel
See all 2,967 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.