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Chester

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Chester Flights as Low as $144

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

Breeze Airways
Thu, May 28 - Sat, May 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$144 Roundtrip, found 6 days ago
$144
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sat, May 30, priced at $144 found 6 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $149 found 3 days ago
Breeze Airways
Thu, May 28 - Sat, May 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sat, May 30, priced at $153 found 6 days ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $154 found 6 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$155 Roundtrip, found 10 hours ago
$155
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $155 found 10 hours ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$159 Roundtrip, found 6 days ago
$159
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $159 found 6 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$160 Roundtrip, found 10 hours ago
$160
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $160 found 10 hours ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $161 found 2 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$164 Roundtrip, found 3 days ago
$164
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, May 28 from Orlando Intl. to Portsmouth Intl., returning Sun, May 31, priced at $164 found 3 days ago
Breeze Airways
Thu, May 28 - Sun, May 31
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$188 Roundtrip, found 9 hours ago
$188
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Thu, May 28 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, May 31, priced at $188 found 9 hours ago
JetBlue Airways
Thu, Sep 3 - Thu, Sep 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$224 Roundtrip, found 3 hours ago
$224
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Sep 3 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Sep 17, priced at $224 found 3 hours ago
JetBlue Airways
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$242 Roundtrip, found 2 hours ago
$242
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $242 found 2 hours ago
American Airlines
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$247 Roundtrip, found 2 hours ago
$247
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $247 found 2 hours ago
United
Tue, Sep 8 - Tue, Sep 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$326 Roundtrip, found 1 day ago
$326
Roundtrip
found 1 day ago
Select United flight, departing Tue, Sep 8 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Sep 29, priced at $326 found 1 day ago
American Airlines
Fri, May 15 - Wed, May 20
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$388 Roundtrip, found 5 days ago
$388
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, May 15 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Wed, May 20, priced at $388 found 5 days ago
American Airlines
Wed, Jun 24 - Wed, Jul 1
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$429 Roundtrip, found 16 hours ago
$429
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Jun 24 from Charlotte-Douglas Intl. to Manchester-Boston Regional, returning Wed, Jul 1, priced at $429 found 16 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 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 May, 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 $144, 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 $144 right now, why wait?

Chester Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$143

Last Minute Hotel Deals in Chester

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 ...
8.4/10 Very Good! (1,023 reviews)
Everything great !

Reviewed on May 10, 2026

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DoubleTree by Hilton Boston - Andover
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! (2,077 reviews)
Definitely need improvement in the rooms. A handle on the dresser was broken and thus the drawer was unusable. Had a thermostat in the room, but it was not hooked up at all. There were people partying in the hotel until 2:00 a.m. with music blasting throughout the entire hotel, but there was no response ...

Reviewed on May 11, 2026

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La Quinta Inn & Suites by Wyndham 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 breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,195 reviews)
When I checked in after unloading, went to use the bathroom and the toilet seat had urine and pubic hair on it. I went down to front desk and they moved me right away. The room was clean the second time. The price was affordable and the women who was working when I checked out was very nice to deal ...

Reviewed on May 12, 2026

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La Quinta Inn & Suites by Wyndham Salem NH
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! (1,020 reviews)
Can’t get coffee until 730 on the weekends did not get our room refreshed asked for clean towels said they couldn’t give us clean towels because they were shortstaffed. Other than that. It was a delightful day. Breakfast was pretty good.

Reviewed on May 11, 2026

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Sonesta ES Suites Andover Boston
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! (1,786 reviews)
Everything was perfect, clean Room, confortable bed and Nice staff. I recommand and Will stay There again

Reviewed on May 7, 2026

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Park View Inn - Salem
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! (1,022 reviews)
They do charge for parking, so be sure to ask the amount. Room very very clean, free breakfast covered every taste from pancakes to eggs, yogurt, cereal, oatmeal, cereal. And free hot coffee or tea 24/7.

Reviewed on May 11, 2026

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Tru by Hilton Manchester Downtown
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! (1,194 reviews)
The issue I ran into was brown water coming out of the faucets on the last day I was there. I was told that there was some kind of maintenance going on (no warning given to the guests) and that the water was fine, but I did not trust it. That issue should have been handled better.

Reviewed on May 11, 2026

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DoubleTree by Hilton Manchester Downtown
Holiday Inn Express Andover North-Lawrence by IHG

Holiday Inn Express Andover North-Lawrence by IHG

2.5 out of 5
224 Winthrop Ave Lawrence MA
Book a stay at this business-friendly hotel in Lawrence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,000 reviews)
Great stay aways

Reviewed on May 12, 2026

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Holiday Inn Express Andover North-Lawrence by IHG
See all 486 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.