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Chester

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Chester Flights as Low as $103

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

Breeze Airways
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 12 hours ago
$103
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 30, priced at $103 found 12 hours ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 8 hours ago
$107
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $107 found 8 hours ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 12 hours ago
$112
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $112 found 12 hours ago
Breeze Airways
Sat, Aug 30 - Sat, Aug 30
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 12 hours ago
$113
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 30, priced at $113 found 12 hours ago
JetBlue Airways
Tue, Nov 4 - Tue, Nov 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$113 Roundtrip, found 5 days ago
$113
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Tue, Nov 4 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Nov 11, priced at $113 found 5 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 12 hours ago
$117
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $117 found 12 hours ago
JetBlue Airways
Sat, Nov 1 - Tue, Nov 11
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$119 Roundtrip, found 5 days ago
$119
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Nov 1 from Orlando Intl. to Manchester-Boston Regional, returning Tue, Nov 11, priced at $119 found 5 days ago
Breeze Airways
Wed, Dec 3 - Wed, Dec 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 12 hours ago
$122
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Wed, Dec 10, priced at $122 found 12 hours ago
Breeze Airways
Sat, Sep 27 - Sat, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 27 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 4, priced at $123 found 2 days ago
Breeze Airways
Sat, Aug 23 - Sat, Aug 23
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Aug 23 from Orlando Intl. to Portsmouth Intl., returning Sat, Aug 23, priced at $123 found 1 day ago
JetBlue Airways
Sat, Nov 1 - Mon, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Nov 1 from Orlando Intl. to Manchester-Boston Regional, returning Mon, Nov 10, priced at $125 found 5 days ago
Breeze Airways
Sat, Sep 27 - Sat, Oct 4
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 2 days ago
$128
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 27 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 4, priced at $128 found 2 days ago
Breeze Airways
Sat, Sep 20 - Sat, Sep 20
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$133 Roundtrip, found 6 days ago
$133
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 20 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 20, priced at $133 found 6 days ago
Breeze Airways
Sat, Sep 20 - Sat, Sep 20
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$143 Roundtrip, found 6 days ago
$143
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 20 from Orlando Intl. to Portsmouth Intl., returning Sat, Sep 20, priced at $143 found 6 days ago
American Airlines
Thu, Nov 6 - Sat, Nov 8
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Nov 6 from Orlando Intl. to Manchester-Boston Regional, returning Sat, Nov 8, priced at $207 found 6 days ago
United
Mon, Nov 3 - Mon, Nov 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$252 Roundtrip, found 5 days ago
$252
Roundtrip
found 5 days ago
Select United flight, departing Mon, Nov 3 from Orlando Intl. to Manchester-Boston Regional, returning Mon, Nov 10, priced at $252 found 5 days 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 August, 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 $103, 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 $103 right now, why wait?

Chester Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$102

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 4-star hotel in Manchester. Enjoy breakfast (surcharge), room service, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,011 reviews)
"Place was nice"

Reviewed on Aug 10, 2025

Get rates
DoubleTree by Hilton Manchester Downtown
Even Hotels Manchester Airport by IHG

Even Hotels Manchester Airport by IHG

3.5 out of 5
55 John E. Devine Drive, Manchester, NH
Stay at this 3.5-star business-friendly hotel in Manchester. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (859 reviews)
"Very nice and new and clean! Great pool!"

Reviewed on Aug 5, 2025

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Even Hotels Manchester Airport by IHG
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
Stay at this 3-star business-friendly hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
8/10 Very Good! (1,823 reviews)
"The water was cloudy is my only problem. Of the rest, perfect."

Reviewed on Aug 8, 2025

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La Quinta Inn & Suites by Wyndham Boston-Andover
Seabrook Inn

Seabrook Inn

2.5 out of 5
9 Stard Rd, Seabrook, NH
Book a stay at this business-friendly motel in Seabrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
6.4/10 (1,008 reviews)
"We had a very comfortable stay, the rooms are great and it's quiet. The staff are very pleasant."

Reviewed on Aug 9, 2025

Get rates
Seabrook Inn
SpringHill Suites by Marriott Boston/Andover

SpringHill Suites by Marriott Boston/Andover

3 out of 5
550 Minuteman Rd, Andover, MA
Stay at this 3-star hotel in Andover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
8.8/10 Excellent! (1,002 reviews)
"We had a short overnight stay, but liked the quiet location in a business park. Nice quick breakfast to start the day.was clean and comfortable. Definitely recommend."

Reviewed on Aug 8, 2025

Get rates
SpringHill Suites by Marriott Boston/Andover
Hampton Motor Inn

Hampton Motor Inn

2 out of 5
869 Lafayette Rd, Hampton, NH
Stay at this motel in Hampton. 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 (697 reviews)
"Great stay.."

Reviewed on Aug 4, 2025

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Hampton Motor Inn
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
Stay at this 3-star 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! (1,238 reviews)
"Well kept. Cute dishes and dishwasher in our little kitchen. Pool hot tub. Loved it!"

Reviewed on Aug 9, 2025

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Best Western Plus Executive Court Inn & Conference Center
Holiday Inn Express Hotel & Suites Seabrook by IHG

Holiday Inn Express Hotel & Suites Seabrook by IHG

2.5 out of 5
11 Rocks Rd, Seabrook, NH
Stay at this hotel in Seabrook. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,007 reviews)
"Very clean and comfortable"

Reviewed on Aug 9, 2025

Get rates
Holiday Inn Express Hotel & Suites Seabrook by IHG
See all 442 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.