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Chester

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Chester Flights as Low as $496

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

American Airlines
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$496 Roundtrip, found 1 hour ago
$496
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $496 found 1 hour ago
American Airlines
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$506 Roundtrip, found 1 hour ago
$506
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $506 found 1 hour ago
American Airlines
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$511 Roundtrip, found 1 hour ago
$511
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $511 found 1 hour ago
United
Wed, Jul 8 - Mon, Aug 31
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$516 Roundtrip, found 2 hours ago
$516
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Mon, Aug 31, priced at $516 found 2 hours ago
American Airlines
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$522 Roundtrip, found 1 hour ago
$522
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $522 found 1 hour ago
United
Wed, Jul 8 - Mon, Aug 31
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$527 Roundtrip, found 2 hours ago
$527
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Mon, Aug 31, priced at $527 found 2 hours ago
American Airlines
Fri, Jul 10 - Tue, Aug 25
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$530 Roundtrip, found 2 hours ago
$530
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Jul 10 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Aug 25, priced at $530 found 2 hours ago
American Airlines
Wed, Jul 8 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$532 Roundtrip, found 2 hours ago
$532
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $532 found 2 hours ago
JetBlue Airways
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$533 Roundtrip, found 1 hour ago
$533
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $533 found 1 hour ago
United
Wed, Jul 8 - Mon, Aug 31
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$537 Roundtrip, found 2 hours ago
$537
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Mon, Aug 31, priced at $537 found 2 hours ago
United
Wed, Jul 8 - Tue, Aug 25
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$537 Roundtrip, found 2 hours ago
$537
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Aug 25, priced at $537 found 2 hours ago
American Airlines
Fri, Jul 10 - Tue, Aug 25
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$540 Roundtrip, found 2 hours ago
$540
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Fri, Jul 10 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Aug 25, priced at $540 found 2 hours ago
JetBlue Airways
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$542 Roundtrip, found 1 hour ago
$542
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $542 found 1 hour ago
American Airlines
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$542 Roundtrip, found 1 hour ago
$542
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $542 found 1 hour ago
American Airlines
Wed, Jul 8 - Mon, Aug 31
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$543 Roundtrip, found 2 hours ago
$543
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Mon, Aug 31, priced at $543 found 2 hours ago
JetBlue Airways
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$558 Roundtrip, found 1 hour ago
$558
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $558 found 1 hour 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 July, 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 $496, 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 $496 right now, why wait?

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$496

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! (434 reviews)
Fun stay at a neat old inn in a very convenient and lovely location, walking distance to good food and shopping. This is an older hotel that doesn’t have all the updated and most modern conveniences but if it did, it would be twice as expensive and I probably would not have stayed there. And it would ...

Reviewed on May 10, 2026

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Fullerton Inn
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! (577 reviews)
Everything was excellent

Reviewed on May 5, 2026

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Woodstock Inn & Resort
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! (1,000 reviews)
Very clean. Well equipped kitchen. Helpful staff.

Reviewed on May 12, 2026

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Pointe at Castle Hill Resort
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! (841 reviews)
We always love this property!!

Reviewed on May 4, 2026

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Kimpton Taconic Hotel by IHG
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 ...
8.2/10 Very Good! (976 reviews)
Great staff. Newly updated decor

Reviewed on May 16, 2026

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Hampton Inn Brattleboro
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! (928 reviews)
Lovely hotel with views of river and walkable to variety of shops and restaurants

Reviewed on May 12, 2026

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The Shire Woodstock
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! (619 reviews)
No coffee makers in the rooms and no coffee service in the lobby except in the morning. No refrigerators in the rooms. Bed was comfortable and clean. Room was spacious and lovely. Hot tub was wonderful. The stay was nice.

Reviewed on May 17, 2026

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The Equinox Golf Resort & Spa
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. ...
8.6/10 Excellent! (881 reviews)
Historic hotel in the heart of downtown, close to everything-- restaurants, galleries, stores, train station. Great location, wonderful staff, movie theater and pub on site!

Reviewed on May 15, 2026

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Latchis Hotel
See all 3,110 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.