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Chester

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Chester Flights as Low as $102

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

Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Avelo Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
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 April, 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 $102, 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 $102 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$101

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! (2,651 reviews)
Easy access to the casino without the casino crowd. Huge room, nice staff. I stayed an extra night.

Reviewed on Feb 19, 2026

Hyatt Place Uncasville - Casino Area
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. ...
7/10 Good! (1,006 reviews)
Good service

Reviewed on Feb 16, 2026

Motel 6 New Haven - Branford, CT
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 ...
9/10 Wonderful! (2,067 reviews)
Excellent hotel!

Reviewed on Feb 19, 2026

Mohegan Sun
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 ...
8.6/10 Excellent! (1,885 reviews)
Room spotless staff friendly and courteous. The location is central , close to casino and highway.

Reviewed on Feb 17, 2026

Microtel Inn & Suites by Wyndham Uncasville Casino Area
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 ...
7.4/10 Good! (1,002 reviews)
Staff was ok, the bath tub wasn’t too clean

Reviewed on Feb 16, 2026

Holiday Inn Norwich by IHG
Hampton Inn Norwich

Hampton Inn Norwich

2.5 out of 5
154 Salem Turnpike Norwich CT
Book a stay at this business-friendly hotel in Norwich. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,006 reviews)
Nice & clean Breakfast delicios 😋 pool salt water very clean. Nice people The reception staff are very friendly and treat you with great respect and courtesy. They explain all the services available for your comfort. ( Michelle 👏) Thank you,

Reviewed on Feb 21, 2026

Hampton Inn Norwich
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 ...
9/10 Wonderful! (1,002 reviews)
Staff was great, very friendly, breakfast was nice. Room was clean. The bed was horrible. Very uncomfortable. Everything else was great.

Reviewed on Feb 16, 2026

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

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Book a stay at this business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (554 reviews)
The hotel staff and accommodations were great. I would highly recommend it.

Reviewed on Jan 17, 2026

Inn at Middletown
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.