Search Cheap Flights toChester
Search 400 airlines and 321,000 hotels worldwide.
Stop Planning & Start Exploring
FREE 24 hour cancellation on most flights
Chester Flights as Low as $102
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 11 hours ago
$102
Roundtrip
found 11 hours ago
Wed, May 21 - Wed, May 21
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 4 days ago
$103
Roundtrip
found 4 days ago
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 11 hours ago
$107
Roundtrip
found 11 hours ago
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 4 days ago
$108
Roundtrip
found 4 days ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Wed, May 21 - Wed, May 21
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 4 days ago
$113
Roundtrip
found 4 days ago
Wed, May 7 - Sat, May 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 4 days ago
$114
Roundtrip
found 4 days ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Wed, May 7 - Sat, May 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$119 Roundtrip, found 4 days ago
$119
Roundtrip
found 4 days ago
Sat, Aug 9 - Sat, Aug 23
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Wed, May 7 - Sat, May 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$124 Roundtrip, found 4 days ago
$124
Roundtrip
found 4 days ago
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$145 Roundtrip, found 1 day ago
$145
Roundtrip
found 1 day ago
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Thu, Jun 12 - Tue, Jun 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
Wed, May 14 - Mon, May 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$201 Roundtrip, found 4 days ago
$201
Roundtrip
found 4 days ago
Wed, May 14 - Mon, May 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$210 Roundtrip, found 4 days ago
$210
Roundtrip
found 4 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 July, 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 $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 | Portsmouth Intl. |
Destination airport IATA code | PSM |
Roundtrip price | $101 |
Last Minute Hotel Deals in Chester
La Quinta Inn & Suites by Wyndham Salem NH
8 Keewaydin Dr, Salem, NH
The price is $105 per night from May 4 to May 5
$105
includes taxes & fees
May 4 - May 5
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 ...
8/10 Very Good! (1,002 reviews)
"Water pressure is very nice"
Reviewed on Apr 29, 2025
Park View Inn - Salem
109 S Broadway, Salem, NH
The price is $103 per night from May 1 to May 2
$103
includes taxes & fees
May 1 - May 2
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. ...
8.6/10 Excellent! (1,336 reviews)
"Always a winner."
Reviewed on Apr 25, 2025
La Quinta Inn & Suites by Wyndham Boston-Andover
131 River Rd, Andover, MA
The price is $137 per night from May 4 to May 5
$137
includes taxes & fees
May 4 - May 5
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 ...
8/10 Very Good! (1,728 reviews)
"Love coming here. There's always room for improvement, we all know this. The only thing I can critique is cleaning."
Reviewed on Apr 29, 2025
Best Western Plus Executive Court Inn & Conference Center
13500 S Willow St, Manchester, NH
The price is $107 per night from May 11 to May 12
$107
includes taxes & fees
May 11 - May 12
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! (1,174 reviews)
"It was delightfully pleasant! Staff was friendly and welcoming 😊"
Reviewed on Apr 28, 2025
Even Hotels Manchester Airport by IHG
55 John E. Devine Drive, Manchester, NH
The price is $113 per night from May 7 to May 8
$113
includes taxes & fees
May 7 - May 8
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 ...
8.6/10 Excellent! (665 reviews)
"I was shocked this hotel was so nice as others dont know to much about it. I was impressed and loved the quality of the rooms and the cleaness was impecable."
Reviewed on Apr 28, 2025
DoubleTree by Hilton Manchester Downtown
700 Elm St., Manchester, NH
The price is $156 per night from May 1 to May 2
$156
includes taxes & fees
May 1 - May 2
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! (1,000 reviews)
"Very clean"
Reviewed on Apr 28, 2025
Holiday Inn Express Andover North-Lawrence by IHG
224 Winthrop Ave, Lawrence, MA
The price is $123 per night from May 5 to May 6
$123
includes taxes & fees
May 5 - May 6
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 ...
8/10 Very Good! (1,003 reviews)
"Everything is perfect, the only thing I didn't like is the TV it doesn'thave YouTube. the room is hygenic, well designed and good value for the price. Secure and worry-free environment. Very good staff 👍"
Reviewed on Apr 28, 2025
DoubleTree by Hilton Boston - Andover
123 Old River Rd, Andover, MA
The price is $151 per night from May 9 to May 10
$151
includes taxes & fees
May 9 - May 10
Stay at this 4-star business-friendly hotel in Andover. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,005 reviews)
Do it
"Amazing everything and everyone was awesome"
Reviewed on Apr 26, 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.
Nearby Cities
Popular Flight Routes
- Atlanta to New York
- Detroit to Las Vegas
- Dallas to Atlanta
- Dallas to Yosemite National Park
- Toronto to Edmonton
- Chicago to Tulum
- Houston to Lake Tahoe
- Chicago to Las Vegas
- Dallas to Miami
- Dallas to Lake Tahoe
- New York to Miami
- New York to Las Vegas
- Miami to Atlanta
- Minneapolis St Paul to Fort Walton Beach Destin
- Dallas to Branson
- Cleveland to Vero Beach
- Managua to Miami
- Atlanta to Boston
- Austin to Tulum
- Calgary to Vancouver
Flights to Our Favorite Destinations
- Flights to Las Vegas
- Flights to New York
- Flights to Orlando
- Flights to Myrtle Beach
- Flights to Chicago
- Flights to Panama City Beach
- Flights to San Diego
- Flights to Miami
- Flights to Destin
- Flights to Los Angeles
- Flights to Boston
- Flights to Nashville
- Flights to Honolulu
- Flights to Gulf Shores
- Flights to Key West
- Flights to Washington
Top Chester Hotels
- La Quinta Inn & Suites by Wyndham Salem NH
- Park View Inn - Salem
- La Quinta Inn & Suites by Wyndham Boston-Andover
- Best Western Plus Executive Court Inn & Conference Center
- Even Hotels Manchester Airport by IHG
- DoubleTree by Hilton Manchester Downtown
- Holiday Inn Express Andover North-Lawrence by IHG
- DoubleTree by Hilton Boston - Andover
- Comfort Inn Airport
- Country Inn & Suites by Radisson, Manchester Airport, NH
- Motel 6 Nashua, NH - South
- SpringHill Suites Manchester-Boston Regional Airport
- Econo Lodge
- Hampton Village Inn
- SpringHill Suites by Marriott Boston/Andover