Search Cheap Flights toChester
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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.
Thu, Oct 16 - Sun, Oct 19
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Thu, Oct 16 - Sun, Oct 19
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Thu, Oct 16 - Sun, Oct 19
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$136 Roundtrip, found 5 days ago
$136
Roundtrip
found 5 days ago
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$141 Roundtrip, found 5 days ago
$141
Roundtrip
found 5 days ago
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, found 4 days ago
$145
Roundtrip
found 4 days ago
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, just found
$145
Roundtrip
just found
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, just found
$148
Roundtrip
just found
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 4 days ago
$150
Roundtrip
found 4 days ago
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, just found
$150
Roundtrip
just found
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$155 Roundtrip, just found
$155
Roundtrip
just found
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$158 Roundtrip, just found
$158
Roundtrip
just found
Mon, Aug 11 - Fri, Aug 15
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$161 Roundtrip, found 6 days ago
$161
Roundtrip
found 6 days ago
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$164 Roundtrip, found 12 hours ago
$164
Roundtrip
found 12 hours ago
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$166 Roundtrip, found 12 hours ago
$166
Roundtrip
found 12 hours ago
Thu, Aug 7 - Thu, Aug 14
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$169 Roundtrip, found 12 hours ago
$169
Roundtrip
found 12 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 October, 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?
Destination airport | Tweed - New Haven Regional |
Destination airport IATA code | HVN |
Roundtrip price | $101 |
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 (1,023 reviews)
"It was good."
Reviewed on Jul 28, 2025
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! (1,953 reviews)
"All around beautiful! Had such a good time!"
Reviewed on Jul 27, 2025
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! (2,494 reviews)
"Close to highway and clean"
Reviewed on Jul 27, 2025
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 ...
9/10 Wonderful! (1,023 reviews)
"Okey breakfast"
Reviewed on Jul 28, 2025
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! (1,734 reviews)
"The room was very spacious. Lots of options in the area. Front staff made ir very easy to check in. Decent breakfast options. Only con was The bathroom was a little dated. You can tell they tried to do quick patch jobs to the cracks in the ceilings and the door didnt evenly close. Otherwise everythings ..."
Reviewed on Jul 27, 2025
Best Western Niantic - New London/Mystic Area
265 Flanders Road, Niantic, CT
Book a stay at this business-friendly hotel in Niantic. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions New London Ferry Dock and Flanders ...
9/10 Wonderful! (302 reviews)
"Brand new motel. Beautiful pool. Convenient to hi-way 95. Breakfast was good and beds are very comfortable."
Reviewed on Jul 25, 2025
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! (1,010 reviews)
"Rooms were large and spacious but quite dark. The Choo Choo lounge and the outside bar were very pleasant. The onsite dining restaurant was disappointing, food was below expectations and did not live up to their rating. Staff were all very pleasant. Parking was a difficult but it is high season."
Reviewed on Jul 21, 2025
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! (1,018 reviews)
Great Stay!
"Good area. Great staff! Great places to eat around the hotel. Had a nice quiet time ."
Reviewed on Jul 28, 2025
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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Top Chester Hotels
- Motel 6 New Haven - Branford, CT
- Hyatt Place Uncasville - Casino Area
- Fairfield by Marriott Inn & Suites Uncasville Mohegan Sun Area
- Microtel Inn & Suites by Wyndham Uncasville Casino Area
- Saybrook Point Resort & Marina
- Clarion Inn
- Quality Inn Old Saybrook - Westbrook
- Holiday Inn Norwich by IHG
- Pier Blue Inn Old Saybrook - Essex
- Sleep Inn & Suites Niantic
- Hampton Inn Norwich
- Red Roof Inn Meriden
- Comfort Inn & Suites
- Red Roof Inn Mystic - New London