Search Cheap Flights to
Chester

Name: Saybrook Point Resort & Marina
Rating: 9.4

Hands down the place to be in Chester!!!!

Photo by Annette Babek

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Chester Flights as Low as $126

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

All deals

One way

Roundtrip

Sun, Aug 10 - Wed, Aug 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$126

Roundtrip

found 14 hours ago

Wed, Aug 13 - Sat, Aug 16

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$128

Roundtrip

found 10 hours ago

Sun, Aug 10 - Wed, Aug 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$131

Roundtrip

found 14 hours ago

Sun, Aug 10 - Wed, Aug 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$136

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$140

Roundtrip

found 14 hours ago

Sat, Jul 26 - Fri, Aug 1

RSW

Southwest Florida Intl.

HVN

Tweed - New Haven Regional

$143

Roundtrip

found 12 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$145

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$151

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$154

Roundtrip

found 14 hours ago

Wed, Jul 9 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$156

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$158

Roundtrip

found 14 hours ago

Wed, Jul 9 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$161

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$162

Roundtrip

found 14 hours ago

Thu, Jul 10 - Sun, Jul 13

MCO

Orlando Intl.

HVN

Tweed - New Haven Regional

$163

Roundtrip

found 14 hours ago

Sun, Jul 27 - Thu, Jul 31

ORD

O'Hare Intl.

HVN

Tweed - New Haven Regional

$181

Roundtrip

found 2 days ago

Thu, Dec 11 - Sun, Dec 14

TPA

Tampa Intl.

HVN

Tweed - New Haven Regional

$354

Roundtrip

found 15 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 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 August, 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 $126, 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 $126 right now, why wait?

Chester Flight Information
Destination airport	Tweed - New Haven Regional
Destination airport IATA code	HVN
Roundtrip price	$125

Last Minute Hotel Deals in Chester

Motel 6 New Haven - Branford, CT

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. ...

6.8/10 (1,006 reviews)

"Inexpensive, clean, and available on very short notice after a minor travel interruption. We were quite satisfied with the accommodations."

Reviewed on Jun 18, 2025

Get rates

Mohegan Sun

1 Mohegan Sun Boulevard, Montville, CT

Stay at this 4.5-star luxury resort in Montville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (1,920 reviews)

"Excellwnt all round"

Reviewed on Jun 24, 2025

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Hyatt Place Uncasville - Casino Area

2049 Norwich, New London Turnpike, Montville, CT

Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

9/10 Wonderful! (2,436 reviews)

"The room was very spacious, bed was very comfortable and it was quiet."

Reviewed on Jun 27, 2025

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Clarion Inn

201 Washington Avenue, North Haven, CT

Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

7.4/10 Good! (1,009 reviews)

"A great stay for our family weekend event. Carpet in the rooms need to be steamed cleaned."

Reviewed on Jun 23, 2025

Get rates

Microtel Inn & Suites by Wyndham Uncasville Casino Area

1954 Norwich New London Tpke, Route 32, 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! (1,697 reviews)

"perfect for the cost and a quick overnight stay"

Reviewed on Jun 24, 2025

Get rates

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

2255 Norwich-New London Turnpike, Montville, CT

Stay at this 3-star business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...

9.2/10 Wonderful! (1,005 reviews)

"Friendly staff, food was good, pool was nice for the kids. We had a great stay."

Reviewed on Jun 24, 2025

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Pier Blue Inn Old Saybrook - Essex

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. ...

7.6/10 Good! (982 reviews)

"This is a great place to stay with an outstanding location in Old Saybrook right on RT 1. Great breakfast cafe right across the street."

Reviewed on Jun 24, 2025

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Saybrook Point Resort & Marina

2 Bridge St, Old Saybrook, CT

Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...

9.4/10 Exceptional! (1,000 reviews)

"Fantastic as always!!"

Reviewed on Jun 24, 2025

Get rates

See all 1,064 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.

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