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Chester

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Chester Flights as Low as $130

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

Breeze Airways
Thu, Mar 26 - Sun, Mar 29
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$130 Roundtrip, found 4 days ago
$130
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Mar 26 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Mar 29, priced at $130 found 4 days ago
Breeze Airways
Thu, Mar 26 - Sun, Mar 29
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Mar 26 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Mar 29, priced at $135 found 4 days ago
Breeze Airways
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$144 Roundtrip, found 14 hours ago
$144
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $144 found 14 hours ago
Breeze Airways
Tue, Apr 14 - Tue, Apr 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$150 Roundtrip, found 3 days ago
$150
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 14 from Orlando Intl. to Portsmouth Intl., returning Tue, Apr 28, priced at $150 found 3 days ago
Breeze Airways
Sat, Jun 6 - Sat, Jun 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$154 Roundtrip, found 14 hours ago
$154
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Sat, Jun 6 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 6, priced at $154 found 14 hours ago
Breeze Airways
Tue, Apr 14 - Tue, Apr 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$155 Roundtrip, found 3 days ago
$155
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 14 from Orlando Intl. to Portsmouth Intl., returning Tue, Apr 28, priced at $155 found 3 days ago
Breeze Airways
Thu, Mar 26 - Sun, Mar 29
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$156 Roundtrip, found 2 days ago
$156
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Mar 26 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Mar 29, priced at $156 found 2 days ago
Breeze Airways
Tue, Apr 14 - Tue, Apr 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Tue, Apr 14 from Orlando Intl. to Portsmouth Intl., returning Tue, Apr 28, priced at $157 found 1 day ago
Breeze Airways
Thu, May 28 - Sat, May 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sat, May 30, priced at $159 found 4 days ago
Breeze Airways
Tue, Apr 14 - Tue, Apr 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$160 Roundtrip, found 3 days ago
$160
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Tue, Apr 14 from Orlando Intl. to Portsmouth Intl., returning Tue, Apr 28, priced at $160 found 3 days ago
Breeze Airways
Tue, Apr 14 - Tue, Apr 28
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$161 Roundtrip, found 8 hours ago
$161
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Tue, Apr 14 from Orlando Intl. to Portsmouth Intl., returning Tue, Apr 28, priced at $161 found 8 hours ago
Breeze Airways
Wed, Apr 1 - Wed, Apr 8
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$211 Roundtrip, found 2 hours ago
$211
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Apr 1 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Apr 8, priced at $211 found 2 hours ago
JetBlue Airways
Tue, Apr 7 - Sat, Apr 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$268 Roundtrip, found 1 hour ago
$268
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Apr 7 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Apr 11, priced at $268 found 1 hour ago
American Airlines
Tue, Apr 7 - Sat, Apr 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$288 Roundtrip, found 1 hour ago
$288
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Apr 7 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Apr 11, priced at $288 found 1 hour ago
United
Tue, Apr 7 - Sat, Apr 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$394 Roundtrip, found 1 hour ago
$394
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Apr 7 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Apr 11, priced at $394 found 1 hour ago
Breeze Airways
Thu, Mar 26 - Sun, Mar 29
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$447 Roundtrip, just found
$447
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Mar 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Mar 29, priced at $447 just found

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 March, 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 $130, 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 $130 right now, why wait?

Chester Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$130

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! (1,147 reviews)
The room was spacious and clean. check I. Went really well, we received the famous chocolate chip cookies ar check in!

Reviewed on Mar 22, 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! (1,007 reviews)
I was under the impression that the continental breakfast came with the room price, I was unpleasantly surprised when I had to pay $50 extra dollars for a breakfast I had already expected to have available to me with the price of the room. That really bothered me.

Reviewed on Mar 22, 2026

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DoubleTree by Hilton Boston - Andover
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! (1,718 reviews)
The staff was friendly and thorough. The rooms were clean and the location was perfect for our visit to a Tuscan village event. The only complaint..if you call it that, would be the room was a bit dated and had some loose wallpaper and chipped corners on walls. Accessible outlets by the beds would ...

Reviewed on Mar 23, 2026

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Park View Inn - Salem
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! (1,125 reviews)
The lobby could be better ventilated and room could be cleaner - towels, lampshade and clogged sink. Otherwise, the hotel is fine for sleeping.

Reviewed on Mar 21, 2026

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La Quinta Inn & Suites by Wyndham Salem NH
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! (1,357 reviews)
The room was clean, staff was friendly. The only issue was the jacuzzi tub in the room was not working as it should.

Reviewed on Mar 23, 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.
9.8/10 Exceptional! (135 reviews)
Great stay

Reviewed on Mar 19, 2026

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Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Hampton Inn Haverhill

Hampton Inn Haverhill

2.5 out of 5
106 Bank Road Haverhill MA
Book a stay at this business-friendly hotel in Haverhill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,002 reviews)
Property was pretty clean, there was a couple of functions going on that night that made for a very busy lobby area, breakfast was 3 out of 5, pool area was small and very crowded.

Reviewed on Mar 19, 2026

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Hampton Inn Haverhill
Tru by Hilton Manchester Downtown

Tru by Hilton Manchester Downtown

2.5 out of 5
135 Spring Street Manchester NH
Book a stay at this business-friendly hotel in Manchester. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
9.2/10 Wonderful! (1,005 reviews)
Nice place to stay. Staff was great! Diamond was super helpful and overall very attentive to our needs.

Reviewed on Mar 23, 2026

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Tru by Hilton Manchester Downtown
See all 479 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.