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Chesterfield

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Chesterfield Flights as Low as $185

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

Breeze Airways
Thu, Nov 26 - Sun, Dec 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$185 Roundtrip, found 3 hours ago
$185
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Dec 13, priced at $185 found 3 hours ago
Breeze Airways
Thu, Nov 26 - Sun, Dec 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Dec 13, priced at $190 found 3 hours ago
Breeze Airways
Thu, Nov 26 - Sun, Dec 13
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Sun, Dec 13, priced at $195 found 3 hours ago
Breeze Airways
Thu, Nov 26 - Thu, Dec 10
RDU
Raleigh - Durham Intl.
MHT
Manchester-Boston Regional
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Manchester-Boston Regional, returning Thu, Dec 10, priced at $205 found 1 day ago
Breeze Airways
Fri, Jan 8 - Fri, Jan 22
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$218 Roundtrip, found 8 hours ago
$218
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa Intl. to Manchester-Boston Regional, returning Fri, Jan 22, priced at $218 found 8 hours ago
Breeze Airways
Fri, Jan 8 - Sun, Jan 10
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$235 Roundtrip, found 9 hours ago
$235
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Orlando Intl. to Manchester-Boston Regional, returning Sun, Jan 10, priced at $235 found 9 hours ago
Southwest Airlines
Thu, Nov 26 - Thu, Dec 3
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$239 Roundtrip, found 12 hours ago
$239
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Thu, Nov 26 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Thu, Dec 3, priced at $239 found 12 hours ago
Southwest Airlines
Fri, Dec 11 - Mon, Dec 14
RSW
Southwest Florida Intl.
MHT
Manchester-Boston Regional
$247 Roundtrip, found 10 hours ago
$247
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Fri, Dec 11 from Southwest Florida Intl. to Manchester-Boston Regional, returning Mon, Dec 14, priced at $247 found 10 hours ago
American Airlines
Fri, Nov 6 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$251 Roundtrip, found 1 hour ago
$251
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Fri, Nov 6 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at $251 found 1 hour ago
United
Fri, Nov 6 - Sat, Nov 14
FLL
Fort Lauderdale - Hollywood Intl.
MHT
Manchester-Boston Regional
$279 Roundtrip, found 1 hour ago
$279
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Nov 6 from Fort Lauderdale - Hollywood Intl. to Manchester-Boston Regional, returning Sat, Nov 14, priced at $279 found 1 hour ago
American Airlines
Tue, Nov 10 - Tue, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
MHT
Manchester-Boston Regional
$281 Roundtrip, found 16 hours ago
$281
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Tue, Nov 10 from Hartsfield-Jackson Atlanta Intl. to Manchester-Boston Regional, returning Tue, Nov 17, priced at $281 found 16 hours ago
American Airlines
Thu, Oct 22 - Sat, Nov 7
DCA
Ronald Reagan Washington National
MHT
Manchester-Boston Regional
$389 Roundtrip, found 5 days ago
$389
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Oct 22 from Ronald Reagan Washington National to Manchester-Boston Regional, returning Sat, Nov 7, priced at $389 found 5 days ago
United
Fri, Nov 6 - Tue, Nov 10
LAX
Los Angeles Intl.
MHT
Manchester-Boston Regional
$442 Roundtrip, just found
$442
Roundtrip
just found
Select United flight, departing Fri, Nov 6 from Los Angeles Intl. to Manchester-Boston Regional, returning Tue, Nov 10, priced at $442 just found
Southwest Airlines
Wed, Dec 23 - Tue, Dec 29
GSP
Greenville-Spartanburg Intl.
MHT
Manchester-Boston Regional
$446 Roundtrip, found 3 days ago
$446
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Wed, Dec 23 from Greenville-Spartanburg Intl. to Manchester-Boston Regional, returning Tue, Dec 29, priced at $446 found 3 days ago
Alaska Airlines
Fri, Nov 6 - Tue, Nov 10
LAX
Los Angeles Intl.
MHT
Manchester-Boston Regional
$789 Roundtrip, just found
$789
Roundtrip
just found
Select Alaska Airlines flight, departing Fri, Nov 6 from Los Angeles Intl. to Manchester-Boston Regional, returning Tue, Nov 10, priced at $789 just found
Accessrail
Wed, Nov 18 - Tue, Dec 1
EKW
Miami Central Brightline Train Station
MHT
Manchester-Boston Regional
$1,254 Roundtrip, found 16 hours ago
$1,254
Roundtrip
found 16 hours ago
Select Accessrail flight, departing Wed, Nov 18 from Miami Central Brightline Train Station to Manchester-Boston Regional, returning Tue, Dec 1, priced at $1,254 found 16 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 November, 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 16 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 Manchester-Boston Regional 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 $185, 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 $185 right now, why wait?

Chesterfield Flight Information
Destination airport
Manchester-Boston Regional
Destination airport IATA code
MHT
Roundtrip price
$185

Last Minute Hotel Deals in Chesterfield

Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.2/10 (103 reviews)
"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."

Reviewed on Oct 20, 2026

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Colonial Motel
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
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. ...
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Latchis Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
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 ...
8.4/10 Very Good! (1,008 reviews)
"Excellent place to stay"

Reviewed on Oct 19, 2026

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Best Western Plus Keene Hotel
The White House Inn

The White House Inn

3.5 out of 5
178 Route 9 East Wilmington VT
Stay at this hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. ...
9.2/10 Wonderful! (381 reviews)
"The staff was amazing here and we absolutely loved our stay. We will be coming back and staying again."

Reviewed on Oct 19, 2026

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The White House Inn
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
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! (889 reviews)
"Was a good room for a one night stay on a road trip."

Reviewed on Oct 18, 2026

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Comfort Inn & Suites Brattleboro I-91
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road Keene NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (1,002 reviews)
"I arrived late and exhausted. Young man at front counter was friendly and efficient. Carpet in hallway slightly warn. Room and bath very clean, no complaints. Bed was large and soft. I slept well. Parking lot safe and quiet. Free breakfast was… nothing special. Other businesses close by. Would definitely ..."

Reviewed on Oct 17, 2026

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Days Inn by Wyndham Keene NH
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
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 ...
8.4/10 Very Good! (1,007 reviews)
"Our room was quiet, clean and very comfortable. Breakfast was nice--more than enough for a decent breakfast before heading out-- waffle maker, toast, yogurt, cold cereal, fruit, juice coffee, and tea, etc. The grounds were beautiful and well kept. The staff was very helpful and parking was super ..."

Reviewed on Oct 19, 2026

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The Putney Inn
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
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 ...
8.2/10 Very Good! (1,000 reviews)
"The room had a smell we couldn't identify. The carpet are dirty. The beds are worn out. The breakfast was not great . Fake eggs! The waffles were okay. The staff weren't welcoming at all. Absolutely not worth $300.00 a night!"

Reviewed on Oct 19, 2026

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Hampton Inn Brattleboro
See all 527 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.