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Chester

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Chester Flights as Low as $216

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

Avelo Airlines
Thu, Jul 23 - Mon, Jul 27
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$216 Roundtrip, found 1 day ago
$216
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Thu, Jul 23 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Mon, Jul 27, priced at $216 found 1 day ago
Avelo Airlines
Thu, Jul 16 - Mon, Jul 20
ATL
Hartsfield-Jackson Atlanta Intl.
HVN
Tweed - New Haven Regional
$266 Roundtrip, found 6 days ago
$266
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Thu, Jul 16 from Hartsfield-Jackson Atlanta Intl. to Tweed - New Haven Regional, returning Mon, Jul 20, priced at $266 found 6 days ago
Avelo Airlines
Wed, Jul 29 - Thu, Jul 30
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Jul 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jul 30, priced at $304 found 1 day ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$306 Roundtrip, found 5 days ago
$306
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $306 found 5 days ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$311 Roundtrip, found 5 days ago
$311
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $311 found 5 days ago
Breeze Airways
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$316 Roundtrip, found 5 days ago
$316
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $316 found 5 days ago
Avelo Airlines
Thu, Jul 30 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$343 Roundtrip, found 5 days ago
$343
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $343 found 5 days ago
Avelo Airlines
Thu, Jul 30 - Fri, Jul 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$358 Roundtrip, found 3 days ago
$358
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Fri, Jul 31, priced at $358 found 3 days ago
Breeze Airways
Mon, Jul 27 - Thu, Jul 30
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$525 Roundtrip, found 5 days ago
$525
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Mon, Jul 27 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jul 30, priced at $525 found 5 days ago
Breeze Airways
Wed, Jul 29 - Thu, Jul 30
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$531 Roundtrip, found 5 days ago
$531
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Thu, Jul 30, priced at $531 found 5 days ago
Breeze Airways
Sat, Aug 1 - Mon, Aug 3
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$561 Roundtrip, found 5 days ago
$561
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Aug 1 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Aug 3, priced at $561 found 5 days ago
Breeze Airways
Sun, Aug 2 - Mon, Aug 3
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$572 Roundtrip, found 5 days ago
$572
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Aug 2 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Aug 3, priced at $572 found 5 days ago
Breeze Airways
Thu, Jul 30 - Fri, Jul 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$593 Roundtrip, found 5 days ago
$593
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Jul 30 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Fri, Jul 31, priced at $593 found 5 days ago
Breeze Airways
Wed, Jul 29 - Fri, Jul 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$598 Roundtrip, found 5 days ago
$598
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Fri, Jul 31, priced at $598 found 5 days ago
Breeze Airways
Wed, Jul 29 - Sun, Aug 2
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$619 Roundtrip, found 5 days ago
$619
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jul 29 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Sun, Aug 2, priced at $619 found 5 days ago
Breeze Airways
Fri, Jul 3 - Thu, Jul 9
IAD
Washington Dulles Intl.
HVN
Tweed - New Haven Regional
$1,123 Roundtrip, found 1 day ago
$1,123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Jul 3 from Washington Dulles Intl. to Tweed - New Haven Regional, returning Thu, Jul 9, priced at $1,123 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 FID 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 Tweed - New Haven Regional 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 $216, 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 $216 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$215

Last Minute Hotel Deals in Chester

Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,697 reviews)
"The overall appearance of the hotel seemed to be a bit run down. Our room had several spots where the ceiling looked like there was water damage and it was not repaired. Breakfast area didn't seem well maintained. I expected more from a Hyatt."

Reviewed on Jun 29, 2026

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Hyatt Place Uncasville - Casino Area
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Book a stay at this business-friendly hotel in Meriden. Enjoy free WiFi, free parking, and a health club. Our guests praise the helpful staff and the clean rooms ...
7.4/10 Good! (1,005 reviews)
"Surprisingly nice hotel for the money. The furniture was a bit worn; but at that price, who cares? The room was very attractive. The front desk responded immediately when we had a minor issue with the room. The staff were very cordial. We had an excellent stay."

Reviewed on Jun 28, 2026

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Red Roof Inn Meriden
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
1954 Norwich New London Tpke Montville CT
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,930 reviews)
"I thought the hotel was nice and comfortable for one night. I stayed with my mom so we could enjoy a comedy show at Mohegan Sun. The shuttle service was a nice bonus—Troy, the shuttle driver, was kind and easy to talk with. The front desk staff was also kind and helpful when needed. I thought the ..."

Reviewed on Jun 29, 2026

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Microtel Inn & Suites by Wyndham Uncasville Casino Area
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,002 reviews)
"staff and parking"

Reviewed on Jun 22, 2026

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Pier Blue Inn Old Saybrook - Essex
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.2/10 Good! (1,010 reviews)
"The worst customer service, they had mysterious charges, toilet didn’t work, and beds were dirty and disgusting. Worst experience of my life!"

Reviewed on Jun 28, 2026

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Motel 6 New Haven - Branford, CT
Holiday Inn Norwich by IHG

Holiday Inn Norwich by IHG

3 out of 5
10 Laura Blvd Norwich CT
Book a stay at this business-friendly hotel in Norwich. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,005 reviews)
"Nice"

Reviewed on Jun 28, 2026

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Holiday Inn Norwich by IHG
Regency Inn & Suites New London, Mystic

Regency Inn & Suites New London, Mystic

2.5 out of 5
269 North Frontage Road New London CT
Book a stay at this family-friendly hotel in New London. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6/10 (1,004 reviews)
"Everything Was Absolutely Great About this Establishment, in fact You Get More Then You Expect and See"

Reviewed on Jun 29, 2026

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Regency Inn & Suites New London, Mystic
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on Jun 25, 2026

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Water's Edge Resort & Spa
See all 1,098 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.