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Chester

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Chester Flights as Low as $103

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

Avelo Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Avelo Airlines
Breeze Airways

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 December, 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 $103, 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 $103 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$103

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! (2,827 reviews)
"In"

Reviewed on Nov 9, 2026

Hyatt Place Uncasville - Casino 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 ...
Mohegan Sun
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. ...
Pier Blue Inn Old Saybrook - Essex
The Spa at Norwich Inn

The Spa at Norwich Inn

3.5 out of 5
607 W Thames St Norwich CT
Book a stay at this spa hotel in Norwich. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (1,007 reviews)
"I had the most relaxing amazing time. I love the spa there and being able to charge meals and things to the room makes it easier when lounging in a robe all day. The staff everywhere was exceptional. I would definitely come back again!"

Reviewed on Nov 9, 2026

The Spa at Norwich Inn
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. ...
Motel 6 New Haven - Branford, CT
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 parking, and a 24-hour front desk. Our guests praise the breakfast and the ...
Microtel Inn & Suites by Wyndham 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! (1,009 reviews)
"Great location. The restaurant / bistro is very good. Try the salmon. Staff accommodating and helpful. Room and facilities were clean and inviting. Would stay again."

Reviewed on Nov 9, 2026

Water's Edge Resort & Spa
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! (1,057 reviews)
"I was charged for making a duplicate reservation and reversed it within 15 minutes. They were inflexible and they said they were not able to remove the charge. I have been traveling extensively for many years and have never had this problem."

Reviewed on Nov 10, 2026

Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
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.