Search Cheap Flights to
Chester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chester Flights as Low as $110

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

Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$110 Roundtrip, found 5 days ago
$110
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $110 found 5 days ago
Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 6 hours ago
$114
Roundtrip
found 6 hours ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $114 found 6 hours ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 12 hours ago
$130
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $130 found 12 hours ago
Avelo Airlines
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 12 hours ago
$130
Roundtrip
found 12 hours ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $130 found 12 hours ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$133 Roundtrip, found 8 hours ago
$133
Roundtrip
found 8 hours ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $133 found 8 hours ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 12 hours ago
$135
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $135 found 12 hours ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$141 Roundtrip, found 12 hours ago
$141
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $141 found 12 hours ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$146 Roundtrip, found 8 hours ago
$146
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $146 found 8 hours ago
Avelo Airlines
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$149 Roundtrip, found 7 hours ago
$149
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $149 found 7 hours ago
Breeze Airways
Fri, Apr 10 - Fri, Apr 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 6 days ago
$150
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Apr 17, priced at $150 found 6 days ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$151 Roundtrip, found 8 hours ago
$151
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $151 found 8 hours ago
Breeze Airways
Fri, Apr 10 - Fri, Apr 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$156 Roundtrip, found 6 days ago
$156
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Apr 17, priced at $156 found 6 days ago
Breeze Airways
Fri, Apr 10 - Fri, Apr 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Apr 17, priced at $161 found 6 days ago
Breeze Airways
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$178 Roundtrip, found 7 hours ago
$178
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $178 found 7 hours ago
Breeze Airways
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$183 Roundtrip, found 7 hours ago
$183
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $183 found 7 hours ago
Breeze Airways
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$188 Roundtrip, found 7 hours ago
$188
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $188 found 7 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 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 $110, 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 $110 right now, why wait?

Chester Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$110

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 ...
9.2/10 Wonderful! (2,659 reviews)
The staff were very helpful & the shuttle driver was very nice.

Reviewed on Mar 16, 2026

Get rates
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 ...
9.2/10 Wonderful! (2,049 reviews)
Everything was just perfect!!!

Reviewed on Mar 16, 2026

Get rates
Mohegan Sun
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! (1,000 reviews)
Disgusting! Enough said

Reviewed on Mar 11, 2026

Get rates
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 WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,876 reviews)
Easy process

Reviewed on Mar 16, 2026

Get rates
Microtel Inn & Suites by Wyndham Uncasville Casino 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 ...
9/10 Wonderful! (558 reviews)
The room was clean and relatively well appointed. Bed was very comfortable as were bed linens. However, we stayed three nights and our room was never cleaned. And, the room across from us had a dog that barked literally every waking minute keeping us awake. We complained the first day and were told ...

Reviewed on Mar 15, 2026

Get rates
Inn at Middletown
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! (1,004 reviews)
Paid $280.00 for a room that was probably worth $99.00( and that’s being nice)..This is a dated hotel,lobby is from the 80’s,the room we were given had wallpaper unglued in spots,the bath had stained ceiling tiles,the tub drain didn’t work( the drain plug wouldn’t stay up resulting in having to stand ...

Reviewed on Mar 14, 2026

Get rates
Holiday Inn Norwich by IHG
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 ...
8.8/10 Excellent! (1,003 reviews)
Clean rooms, friendly and helpful staff. Wonderful breakfast. Highly recommend.

Reviewed on Mar 15, 2026

Get rates
The Spa at Norwich Inn
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! (1,000 reviews)
Friendly staff and close to Mohegan Sun

Reviewed on Mar 12, 2026

Get rates
Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
See all 1,066 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.