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Chesterfield

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Chesterfield Flights as Low as $102

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

Breeze Airways
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$102 Roundtrip, found 16 hours ago
$102
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Wed, May 7 from Orlando Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $102 found 16 hours ago
Breeze Airways
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$107 Roundtrip, found 16 hours ago
$107
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Wed, May 7 from Orlando Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $107 found 16 hours ago
Breeze Airways
Wed, May 14 - Mon, May 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$111 Roundtrip, found 4 days ago
$111
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 14 from Orlando Intl. to Manchester-Boston Regional, returning Mon, May 19, priced at $111 found 4 days ago
Breeze Airways
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$112 Roundtrip, found 16 hours ago
$112
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Wed, May 7 from Orlando Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $112 found 16 hours ago
Breeze Airways
Wed, May 14 - Mon, May 19
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$116 Roundtrip, found 4 days ago
$116
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, May 14 from Orlando Intl. to Manchester-Boston Regional, returning Mon, May 19, priced at $116 found 4 days ago
JetBlue Airways
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, May 7 from Orlando Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $137 found 16 hours ago
American Airlines
Wed, May 21 - Wed, May 28
CLT
Charlotte-Douglas Intl.
MHT
Manchester-Boston Regional
$145 Roundtrip, found 6 days ago
$145
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, May 21 from Charlotte-Douglas Intl. to Manchester-Boston Regional, returning Wed, May 28, priced at $145 found 6 days ago
American Airlines
Wed, May 14 - Tue, May 20
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$200 Roundtrip, found 17 hours ago
$200
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Wed, May 14 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Tue, May 20, priced at $200 found 17 hours ago
United
Wed, May 7 - Wed, May 21
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$207 Roundtrip, found 16 hours ago
$207
Roundtrip
found 16 hours ago
Select United flight, departing Wed, May 7 from Orlando Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $207 found 16 hours ago
Bargain Flight
Tue, May 13 - Tue, May 20
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$240 Roundtrip, found 16 hours ago
$240
Roundtrip
found 16 hours ago
Select Bargain Flight flight, departing Tue, May 13 from Hartsfield-Jackson Atlanta Intl. to Manchester-Boston Regional, returning Tue, May 20, priced at $240 found 16 hours ago
JetBlue Airways
Wed, Jun 25 - Tue, Jul 1
PIT
Pittsburgh Intl.
MHT
Manchester-Boston Regional
$241 Roundtrip, found 17 hours ago
$241
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Wed, Jun 25 from Pittsburgh Intl. to Manchester-Boston Regional, returning Tue, Jul 1, priced at $241 found 17 hours ago
American Airlines
Tue, May 20 - Sat, May 24
GSO
Piedmont Triad Intl.
MHT
Manchester-Boston Regional
$253 Roundtrip, found 2 days ago
$253
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 20 from Piedmont Triad Intl. to Manchester-Boston Regional, returning Sat, May 24, priced at $253 found 2 days ago
American Airlines
Tue, May 20 - Wed, May 21
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$275 Roundtrip, found 2 days ago
$275
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 20 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Wed, May 21, priced at $275 found 2 days ago
American Airlines
Thu, May 15 - Sun, May 18
HHH
Hilton Head Island
MHT
Manchester-Boston Regional
$373 Roundtrip, found 17 hours ago
$373
Roundtrip
found 17 hours ago
Select American Airlines flight, departing Thu, May 15 from Hilton Head Island to Manchester-Boston Regional, returning Sun, May 18, priced at $373 found 17 hours ago
American Airlines
Tue, Jun 17 - Tue, Jul 1
PNS
Pensacola Intl.
MHT
Manchester-Boston Regional
$381 Roundtrip, found 4 days ago
$381
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jun 17 from Pensacola Intl. to Manchester-Boston Regional, returning Tue, Jul 1, priced at $381 found 4 days ago
American Airlines
Wed, May 7 - Thu, May 15
PHL
Philadelphia Intl.
MHT
Manchester-Boston Regional
$443 Roundtrip, found 11 hours ago
$443
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, May 7 from Philadelphia Intl. to Manchester-Boston Regional, returning Thu, May 15, priced at $443 found 11 hours ago

Cheap Flights to Chesterfield

Fall in love at first flight with your vacation to Chesterfield 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 Chesterfield on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chesterfield, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chesterfield

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chesterfield 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 VSF airport.

What is the cheapest month to fly to Chesterfield?

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 Chesterfield are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chesterfield?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Chesterfield.

What airport is best to fly into Chesterfield?

When you’re planning your trip to Chesterfield, convenience is the name of the game. Luckily, Chesterfield Hartness State Airport is nearby so you can deplane and get going on checking off everything on your Chesterfield must-do list.

How much are flights to Chesterfield?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chesterfield 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 Chesterfield?

The trick to saving a stack of cash on your flight to Chesterfield? 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?

Chesterfield Flight Information
Destination airport
Manchester-Boston Regional
Destination airport IATA code
MHT
Roundtrip price
$101

Last Minute Hotel Deals in Chesterfield

Hampton Inn Brattleboro
Hampton Inn Brattleboro
2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is $112 per night from Apr 28 to Apr 29
$112
includes taxes & fees
Apr 28 - Apr 29
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8/10 Very Good! (813 reviews)
Will stay there again
"Robert the guest service person was extremely professional and friendly when we checked in. The room was clean. The breakfast was adequate. Had an issue hooking up to the WiFI - also the pool wasn’t available- we did tell the front desk in the morning that the tub was not draining. We hadn’t brought ..."

Reviewed on Apr 8, 2025

Hampton Inn Brattleboro
The Putney Inn
The Putney Inn
2.5 out of 5
57 Putney Landing Rd, Putney, VT
The price is $102 per night from Apr 20 to Apr 21
$102
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,000 reviews)
"Good basic hotel. Very clean. Very reasonably priced"

Reviewed on Apr 5, 2025

The Putney Inn
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $120 per night from Apr 17 to Apr 18
$120
includes taxes & fees
Apr 17 - Apr 18
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,000 reviews)
"The sauna after a ski day is great"

Reviewed on Apr 10, 2025

Colonial Motel And Spa
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
The price is $119 per night from Apr 22 to Apr 23
$119
includes taxes & fees
Apr 22 - Apr 23
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (616 reviews)
"All nice"

Reviewed on Apr 5, 2025

Comfort Inn & Suites Brattleboro I-91
Courtyard by Marriott Keene Downtown
Courtyard by Marriott Keene Downtown
3 out of 5
75 Railroad St, Keene, NH
The price is $151 per night from Apr 20 to Apr 21
$151
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Keene. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,008 reviews)
"Great location! Nice staff. Clean."

Reviewed on Apr 13, 2025

Courtyard by Marriott Keene Downtown
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3 out of 5
401 Winchester St, Keene, NH
The price is $136 per night from Apr 20 to Apr 21
$136
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.2/10 Very Good! (1,001 reviews)
"Property was nice and clean, staff was friendly. In walking distance to many fast food/restaurant stops and even had one right next door."

Reviewed on Apr 10, 2025

Best Western Plus Keene Hotel
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHG
2.5 out of 5
100 Chickering Drive, Brattleboro, VT
The price is $158 per night from Apr 27 to Apr 28
$158
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (979 reviews)
"Great property. There is not a lot in the area, but the hotel is really quiet and clean! Large rooms and friendly staff!!"

Reviewed on Apr 7, 2025

Holiday Inn Express Hotel & Suites Brattleboro by IHG
Latchis Hotel
Latchis Hotel
2.5 out of 5
50 Main Street, Brattleboro, VT
The price is $144 per night from Apr 17 to Apr 18
$144
includes taxes & fees
Apr 17 - Apr 18
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (726 reviews)
"The ambience of the Latchis makes it a favorite place to stay. I’ve stayed there many times on business trips and have never been disappointed."

Reviewed on Apr 13, 2025

Latchis Hotel
See all 506 properties in Chesterfield
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.