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Chester

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Chester Flights as Low as $393

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

Avelo Airlines
Wed, Nov 25 - Sun, Nov 29
USA
Concord Regional
HVN
Tweed - New Haven Regional
$393 Roundtrip, found 1 day ago
$393
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Nov 25 from Concord Regional to Tweed - New Haven Regional, returning Sun, Nov 29, priced at $393 found 1 day ago
Breeze Airways
Mon, Aug 31 - Thu, Sep 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$791 Roundtrip, found 16 hours ago
$791
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 31 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 17, priced at $791 found 16 hours ago
Breeze Airways
Tue, Sep 1 - Thu, Sep 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$801 Roundtrip, found 16 hours ago
$801
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 17, priced at $801 found 16 hours ago
Breeze Airways
Sun, Aug 30 - Thu, Sep 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$804 Roundtrip, found 16 hours ago
$804
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, Aug 30 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 17, priced at $804 found 16 hours ago
Breeze Airways
Thu, Aug 27 - Thu, Sep 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$808 Roundtrip, found 16 hours ago
$808
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 17, priced at $808 found 16 hours ago
Breeze Airways
Mon, Aug 31 - Sun, Sep 13
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$816 Roundtrip, found 16 hours ago
$816
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 31 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $816 found 16 hours ago
Breeze Airways
Sun, Aug 23 - Thu, Sep 10
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$818 Roundtrip, found 16 hours ago
$818
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, Aug 23 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 10, priced at $818 found 16 hours ago
Breeze Airways
Tue, Sep 1 - Sun, Sep 13
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$826 Roundtrip, found 16 hours ago
$826
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Tue, Sep 1 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $826 found 16 hours ago
Breeze Airways
Sun, Aug 16 - Sun, Aug 30
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$828 Roundtrip, found 16 hours ago
$828
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, Aug 16 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Sun, Aug 30, priced at $828 found 16 hours ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 13
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$829 Roundtrip, found 16 hours ago
$829
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, Aug 30 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $829 found 16 hours ago
Breeze Airways
Fri, Jul 24 - Thu, Aug 13
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$831 Roundtrip, found 16 hours ago
$831
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Fri, Jul 24 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Aug 13, priced at $831 found 16 hours ago
Breeze Airways
Sun, Aug 9 - Tue, Aug 25
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$832 Roundtrip, found 16 hours ago
$832
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Sun, Aug 9 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Tue, Aug 25, priced at $832 found 16 hours ago
Breeze Airways
Thu, Aug 27 - Sun, Sep 13
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$833 Roundtrip, found 16 hours ago
$833
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Aug 27 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $833 found 16 hours ago
Breeze Airways
Mon, Aug 10 - Tue, Aug 25
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$834 Roundtrip, found 16 hours ago
$834
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Mon, Aug 10 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Tue, Aug 25, priced at $834 found 16 hours ago
Breeze Airways
Tue, Aug 4 - Mon, Aug 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$837 Roundtrip, found 16 hours ago
$837
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Tue, Aug 4 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Mon, Aug 17, priced at $837 found 16 hours ago
Breeze Airways
Fri, Aug 28 - Thu, Sep 17
CVG
Cincinnati - Northern Kentucky Intl.
HVN
Tweed - New Haven Regional
$838 Roundtrip, found 16 hours ago
$838
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Fri, Aug 28 from Cincinnati - Northern Kentucky Intl. to Tweed - New Haven Regional, returning Thu, Sep 17, priced at $838 found 16 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 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 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 $393, 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 $393 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$392

Last Minute Hotel Deals in Chester

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! (1,023 reviews)
"Exactly what I was looking for and an incredibly pleasant stay for a business trip, cheers!"

Reviewed on Jun 15, 2026

Get rates
Motel 6 New Haven - Branford, CT
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! (2,686 reviews)
"It was a nice stay"

Reviewed on Jun 18, 2026

Get rates
Hyatt Place Uncasville - Casino Area
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! (1,005 reviews)
"The spa was nice. The pool can be busy, but the beach side was calm."

Reviewed on Jun 16, 2026

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Water's Edge Resort & Spa
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 (1,016 reviews)
"DO NOT STAY AT THIS HOTEL!!!!! This was by far the worst hotel experience of my entire life. Lobby and hallways smell like cigarettes and weed. After waiting 30 min to check in because of “internet” I was given a room with disgusting used silverware on the bed. After refusing that 20 Min later I ..."

Reviewed on Jun 16, 2026

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Regency Inn & Suites New London, Mystic
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! (1,934 reviews)
"Being older, it was difficult taking a shower. Wish there was a walk in shower"

Reviewed on Jun 14, 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! (1,000 reviews)
"very nice stay"

Reviewed on Jun 15, 2026

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Pier Blue Inn Old Saybrook - Essex
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area

3 out of 5
2255 Norwich-New London Turnpike 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 ...
9.2/10 Wonderful! (1,021 reviews)
"I was SO impressed with this hotel. Front desk staff were informative, friendly and efficient! Comfy room. Food kiosk was much appreciated!! Close to venue we were visiting and convenient shuttle bus service! We will definitely be back !!! Thank you !"

Reviewed on Jun 16, 2026

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Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
Mohegan Sun

Mohegan Sun

4.5 out of 5
1 Mohegan Sun Boulevard Montville CT
Book a stay at this luxury resort in Montville. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,978 reviews)
"Teddy swims concert was amazing. Great venue to see a show. Rooms clean and Italian restaurant was excellent. JR"

Reviewed on Jun 10, 2026

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Mohegan Sun
See all 1,092 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.