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Chester

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Chester Flights as Low as $111

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

Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $111 found 2 days ago
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$115 Roundtrip, found 2 days ago
$115
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $115 found 2 days ago
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$116 Roundtrip, found 2 days ago
$116
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $116 found 2 days ago
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $118 just found
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$121 Roundtrip, just found
$121
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $121 just found
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, just found
$123
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $123 just found
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $125 found 2 days ago
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $128 just found
Breeze Airways
Thu, Apr 16 - Sun, May 3
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, just found
$132
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Apr 16 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, May 3, priced at $132 just found
American Airlines
Tue, May 5 - Wed, May 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$190 Roundtrip, just found
$190
Roundtrip
just found
Select American Airlines flight, departing Tue, May 5 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, May 13, priced at $190 just found
Breeze Airways
Sun, Jun 21 - Thu, Jul 2
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$190 Roundtrip, found 6 days ago
$190
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 21 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Jul 2, priced at $190 found 6 days ago
American Airlines
Tue, May 12 - Sat, May 23
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$195 Roundtrip, found 2 days ago
$195
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 12 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Sat, May 23, priced at $195 found 2 days ago
Breeze Airways
Sun, Jun 21 - Thu, Jul 2
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$195 Roundtrip, found 6 days ago
$195
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Jun 21 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Jul 2, priced at $195 found 6 days ago
United
Tue, May 5 - Wed, May 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$195 Roundtrip, just found
$195
Roundtrip
just found
Select United flight, departing Tue, May 5 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, May 13, priced at $195 just found
American Airlines
Mon, Jun 29 - Sat, Jul 4
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$407 Roundtrip, found 1 day ago
$407
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jun 29 from Hartsfield-Jackson Atlanta Intl. to Manchester-Boston Regional, returning Sat, Jul 4, priced at $407 found 1 day ago
JetBlue Airways
Wed, Apr 29 - Fri, May 1
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$497 Roundtrip, found 1 day ago
$497
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to Manchester-Boston Regional, returning Fri, May 1, priced at $497 found 1 day 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 MHT 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 Manchester-Boston 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 $111, 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 $111 right now, why wait?

Chester Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$111

Last Minute Hotel Deals in Chester

DoubleTree by Hilton Manchester Downtown

DoubleTree by Hilton Manchester Downtown

4 out of 5
700 Elm St. Manchester NH
Stay at this hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
9.2/10 Wonderful! (1,166 reviews)
I didn't eat breakfast here.

Reviewed on Apr 13, 2026

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DoubleTree by Hilton Manchester Downtown
DoubleTree by Hilton Boston - Andover

DoubleTree by Hilton Boston - Andover

4 out of 5
123 Old River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,009 reviews)
Very nice! Staff upon arrival were very friendly and welcoming. Very clean room!

Reviewed on Apr 13, 2026

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DoubleTree by Hilton Boston - Andover
La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

3 out of 5
8 Keewaydin Dr Salem NH
Book a stay at this business-friendly hotel in Salem. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,159 reviews)
Room and hotel were clean. Breakfast was average. They had bagels, eggs, sausage, waffles, ect. Nice workout room. Staff was pleasant and greeting, all though some need deodorant. Only complaint really is the needs can use new mattresses. The mattress is worn in alot.

Reviewed on Apr 13, 2026

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La Quinta Inn & Suites by Wyndham Salem NH
Park View Inn - Salem

Park View Inn - Salem

2 out of 5
109 S Broadway Salem NH
Stay at this motel in Salem. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,742 reviews)
Everything was good only complaint is I have been staying here for quite a few years and the last few times neighbors were very noisy in the early morning like 1:00 am noise. But staff, and everything else is great. Maybe just inform in room and staff that quite time is at 10:00pm

Reviewed on Apr 13, 2026

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Park View Inn - Salem
Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

3 out of 5
13500 S Willow St Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.2/10 Very Good! (1,362 reviews)
Good breakfast, Good and safe parking

Reviewed on Apr 12, 2026

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Best Western Plus Executive Court Inn & Conference Center
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2 out of 5
76 Mountain Rd Epsom NH
Stay at this cabin in Epsom. Enjoy free parking, patios, and climate control. Popular attractions James Park and Epsom Public Library are located nearby.
9.6/10 Exceptional! (141 reviews)
Can 9 was very cozy and provided what we needed very well. I would suggest having a small mirror on desk or in bathroom. Also, although water was hot and enough it may be good to share there is about 5 gallons of hot water before it heats up which is helpful to be prepared to take an efficient ...

Reviewed on Apr 12, 2026

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Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
La Quinta Inn & Suites by Wyndham Boston-Andover

La Quinta Inn & Suites by Wyndham Boston-Andover

3 out of 5
131 River Rd Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8.2/10 Very Good! (2,038 reviews)
I was there for 4 nights and didn’t receive any housekeeping. I was told that I’d need to put in a request on the 3rd day, I did that and still no housekeeping. No clean towels, or trash bags. Before I left I brought it to the front desk and the guy seemed like he didn’t care at all. (didn’t get ...

Reviewed on Apr 13, 2026

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La Quinta Inn & Suites by Wyndham Boston-Andover
Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

3 out of 5
4 Tech Drive Andover MA
Book a stay at this business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and ...
9/10 Wonderful! (1,016 reviews)
I was looking forward to the outside pool when the staff told me that outside pool is out of service until the Summer. I was bummed by that. I wish that the establishment was clear when I reserved their room because I would of went somewhere else to stay.

Reviewed on Apr 13, 2026

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Sonesta ES Suites Andover Boston
See all 485 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.