Search Cheap Flights to
Chesterfield

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chesterfield Flights as Low as $179

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

Breeze Airways
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$179 Roundtrip, found 14 hours ago
$179
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $179 found 14 hours ago
Breeze Airways
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$184 Roundtrip, found 14 hours ago
$184
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $184 found 14 hours ago
Breeze Airways
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$189 Roundtrip, found 14 hours ago
$189
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $189 found 14 hours ago
American Airlines
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$198 Roundtrip, found 14 hours ago
$198
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $198 found 14 hours ago
Breeze Airways
Thu, Sep 3 - Thu, Sep 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Sep 17, priced at $215 found 2 days ago
Breeze Airways
Thu, Sep 3 - Thu, Sep 17
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$225 Roundtrip, found 2 days ago
$225
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando Intl. to Manchester-Boston Regional, returning Thu, Sep 17, priced at $225 found 2 days ago
American Airlines
Wed, Jul 15 - Wed, Jul 29
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$234 Roundtrip, found 14 hours ago
$234
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Jul 15 from Orlando Intl. to Manchester-Boston Regional, returning Wed, Jul 29, priced at $234 found 14 hours ago
United
Tue, Jul 14 - Fri, Jul 31
MCO
Orlando Intl.
MHT
Manchester-Boston Regional
$240 Roundtrip, found 2 days ago
$240
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 14 from Orlando Intl. to Manchester-Boston Regional, returning Fri, Jul 31, priced at $240 found 2 days ago
Bargain Flight
Sat, Jul 11 - Sat, Jul 18
PHL
Philadelphia Intl.
MHT
Manchester-Boston Regional
$246 Roundtrip, found 18 hours ago
$246
Roundtrip
found 18 hours ago
Select Bargain Flight flight, departing Sat, Jul 11 from Philadelphia Intl. to Manchester-Boston Regional, returning Sat, Jul 18, priced at $246 found 18 hours ago
American Airlines
Tue, Sep 8 - Tue, Sep 15
SLC
Salt Lake City Intl.
MHT
Manchester-Boston Regional
$355 Roundtrip, found 1 day ago
$355
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 8 from Salt Lake City Intl. to Manchester-Boston Regional, returning Tue, Sep 15, priced at $355 found 1 day ago
American Airlines
Wed, Nov 4 - Sun, Nov 8
IAH
George Bush Intercontinental
MHT
Manchester-Boston Regional
$406 Roundtrip, found 14 hours ago
$406
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Nov 4 from George Bush Intercontinental to Manchester-Boston Regional, returning Sun, Nov 8, priced at $406 found 14 hours ago
American Airlines
Tue, Jul 28 - Tue, Aug 4
IND
Indianapolis Intl.
MHT
Manchester-Boston Regional
$406 Roundtrip, found 1 day ago
$406
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jul 28 from Indianapolis Intl. to Manchester-Boston Regional, returning Tue, Aug 4, priced at $406 found 1 day ago
American Airlines
Sat, Jul 11 - Sat, Jul 18
TTN
Mercer
MHT
Manchester-Boston Regional
$472 Roundtrip, found 18 hours ago
$472
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Sat, Jul 11 from Mercer to Manchester-Boston Regional, returning Sat, Jul 18, priced at $472 found 18 hours ago
United
Wed, Aug 19 - Wed, Aug 26
EWR
Newark Liberty Intl. Airport
MHT
Manchester-Boston Regional
$489 Roundtrip, found 18 hours ago
$489
Roundtrip
found 18 hours ago
Select United flight, departing Wed, Aug 19 from Newark Liberty Intl. Airport to Manchester-Boston Regional, returning Wed, Aug 26, priced at $489 found 18 hours ago
American Airlines
Tue, Jun 30 - Wed, Jul 8
TPA
Tampa Intl.
MHT
Manchester-Boston Regional
$590 Roundtrip, found 1 day ago
$590
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jun 30 from Tampa Intl. to Manchester-Boston Regional, returning Wed, Jul 8, priced at $590 found 1 day ago
JetBlue Airways
Wed, Jul 1 - Sun, Jul 5
EWR
Newark Liberty Intl. Airport
MHT
Manchester-Boston Regional
$1,085 Roundtrip, found 6 days ago
$1,085
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jul 1 from Newark Liberty Intl. Airport to Manchester-Boston Regional, returning Sun, Jul 5, priced at $1,085 found 6 days 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 July, 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 $179, 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 $179 right now, why wait?

Chesterfield Flight Information
Destination airport
Manchester-Boston Regional
Destination airport IATA code
MHT
Roundtrip price
$178

Last Minute Hotel Deals in Chesterfield

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. ...
8.6/10 Excellent! (905 reviews)
"Love the historical aspects of this place."

Reviewed on Jun 17, 2026

Get rates
Latchis Hotel
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! (1,000 reviews)
"Our room smelled like mold, likely because there was a lot of rotting and what looked like mold in the bathroom. The carpets themselves needed to be replaced as they had a musty smell likely from too much moisture or spills. This hotel really needs a lot of work to make it feel inviting. Any fixes ..."

Reviewed on Jun 16, 2026

Get rates
Days Inn by Wyndham Keene NH
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! (995 reviews)
"Room clean if just a bit worn. Sheets had better days. Helpful staff."

Reviewed on Jun 15, 2026

Get rates
Hampton Inn Brattleboro
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! (1,002 reviews)
"Checked in and hour after booking, room was perfect my needs, breakfast was delicious."

Reviewed on Jun 16, 2026

Get rates
Best Western Plus Keene Hotel
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
360 Viking Village Drive Guilford VT
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (198 reviews)
"We loved staying here! We had everything we needed, and then some! What about amazing experience. We will definitely be back. Such wonderful and creative place to relax and feel at home."

Reviewed on Jun 9, 2026

Get rates
Vikings Villages Resort
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 ...
8.6/10 Excellent! (1,000 reviews)
"Excellent basic comfortable hotel room. There is a fridge and microwave, the hotel was quiet, and the staff were courteous. Everything was very clean. Location is convenient. Highly recommended!"

Reviewed on Jun 14, 2026

Get rates
The Putney Inn
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd 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 ...
8.6/10 Excellent! (1,002 reviews)
"The safety latch on my room door was broken. The staff was very helpful and found a different room for me and got a cart and offered to help. The new room had a dried coffee spill near the fridge and the body wash in the shower was empty or broken- minor inconvenience. Overall a nice stay at a great ..."

Reviewed on Jun 17, 2026

Get rates
Keene Elm City Hotel, an Ascend Collection Hotel
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 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 breakfast and the helpful ...
7.6/10 Good! (1,000 reviews)
"Tranquille et personnel gentils. Petit déjeuner copieux et bon."

Reviewed on Jun 10, 2026

Get rates
The Covered Bridge Inn
See all 519 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.