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Chesterfield

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Chesterfield Flights as Low as $92

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

Spirit Airlines
Wed, May 21 - Tue, May 27
MCO
Orlando Intl.
BOS
Logan Intl.
$92 Roundtrip, found 15 hours ago
$92
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Wed, May 21 from Orlando Intl. to Logan Intl., returning Tue, May 27, priced at $92 found 15 hours ago
Breeze Airways
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 9 hours ago
$102
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Portsmouth Intl., returning Wed, Aug 13, priced at $102 found 9 hours ago
Breeze Airways
Wed, May 21 - Wed, May 21
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$103 Roundtrip, found 5 days ago
$103
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, May 21 from Orlando Intl. to Portsmouth Intl., returning Wed, May 21, priced at $103 found 5 days ago
Spirit Airlines
Fri, May 23 - Tue, May 27
MCO
Orlando Intl.
BOS
Logan Intl.
$105 Roundtrip, found 15 hours ago
$105
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, May 23 from Orlando Intl. to Logan Intl., returning Tue, May 27, priced at $105 found 15 hours ago
Breeze Airways
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 9 hours ago
$107
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Portsmouth Intl., returning Wed, Aug 13, priced at $107 found 9 hours ago
Breeze Airways
Wed, Jun 4 - Sat, Jun 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$108 Roundtrip, found 5 days ago
$108
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 4 from Orlando Intl. to Portsmouth Intl., returning Sat, Jun 7, priced at $108 found 5 days ago
Frontier Airlines
Thu, Jun 12 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 6 days ago
$109
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jun 12 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $109 found 6 days ago
Spirit Airlines
Fri, May 23 - Sun, May 25
MCO
Orlando Intl.
BOS
Logan Intl.
$110 Roundtrip, found 15 hours ago
$110
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, May 23 from Orlando Intl. to Logan Intl., returning Sun, May 25, priced at $110 found 15 hours ago
Breeze Airways
Wed, Jul 9 - Wed, Aug 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 9 hours ago
$112
Roundtrip
found 9 hours ago
Select Breeze Airways flight, departing Wed, Jul 9 from Orlando Intl. to Portsmouth Intl., returning Wed, Aug 13, priced at $112 found 9 hours ago
Spirit Airlines
Tue, Jun 3 - Thu, Jun 5
MCO
Orlando Intl.
BOS
Logan Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Tue, Jun 3 from Orlando Intl. to Logan Intl., returning Thu, Jun 5, priced at $112 found 5 days ago
Breeze Airways
Wed, May 7 - Sat, May 10
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$114 Roundtrip, found 5 days ago
$114
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, May 7 from Orlando Intl. to Portsmouth Intl., returning Sat, May 10, priced at $114 found 5 days ago
Frontier Airlines
Sun, Jun 15 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$117 Roundtrip, found 6 days ago
$117
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sun, Jun 15 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $117 found 6 days ago
JetBlue Airways
Sat, May 24 - Sat, May 24
MCO
Orlando Intl.
BDL
Bradley Intl.
$195 Roundtrip, found 15 hours ago
$195
Roundtrip
found 15 hours ago
Select JetBlue Airways flight, departing Sat, May 24 from Orlando Intl. to Bradley Intl., returning Sat, May 24, priced at $195 found 15 hours ago
United
Wed, Jun 11 - Tue, Jun 17
MCO
Orlando Intl.
BOS
Logan Intl.
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Select United flight, departing Wed, Jun 11 from Orlando Intl. to Logan Intl., returning Tue, Jun 17, priced at $195 found 5 days ago
American Airlines
Tue, May 13 - Tue, May 20
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 8 hours ago
$199
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Tue, May 13 from Orlando Intl. to Logan Intl., returning Tue, May 20, priced at $199 found 8 hours ago
Delta
Tue, May 20 - Wed, May 28
MCO
Orlando Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 15 hours ago
$217
Roundtrip
found 15 hours ago
Select Delta flight, departing Tue, May 20 from Orlando Intl. to Bradley Intl., returning Wed, May 28, priced at $217 found 15 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 CEF 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 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 Barnes Municipal 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 $92, 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 $92 right now, why wait?

Chesterfield Flight Information
Destination airport
Logan Intl.
Destination airport IATA code
BOS
Roundtrip price
$91

Last Minute Hotel Deals in Chesterfield

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
The price is $141 per night from May 4 to May 5
$141
includes taxes & fees
May 4 - May 5
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,297 reviews)
"You have a real shortage of electric outlets in the room for this day and age. Since the hotel used three of the 4 outlets for its own needs, there was only one left, plus a couple at the phone. We had to use the ones in the bathroom to meet all our needs. Easily fixed."

Reviewed on Apr 28, 2025

D. Hotel Suites & Spa
Howard Johnson by Wyndham Amherst Hadley
Howard Johnson by Wyndham Amherst Hadley
2 out of 5
401 Russell St, Hadley, MA
The price is $122 per night from May 4 to May 5
$122
includes taxes & fees
May 4 - May 5
Stay at this hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
7.2/10 Good! (1,001 reviews)
"Very friendly staff; breakfast was decent; Very confusing to find rooms 1001-3; room was very low on toilet paper and tissues when we got there; the sidewalks in the front had over grown trees covering them; the hotel overall felt clean and safe."

Reviewed on Apr 21, 2025

Howard Johnson by Wyndham Amherst Hadley
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
400 Russell St, Hadley, MA
The price is $141 per night from May 5 to May 6
$141
includes taxes & fees
May 5 - May 6
Book a stay at this business-friendly hotel in Hadley. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (1,000 reviews)
"loved it , would recommend and come again only downfall was our card randomly stopped working but they were communicative with us and got it back working quickly"

Reviewed on Apr 28, 2025

Comfort Inn & Suites
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
The price is $96 per night from May 18 to May 19
$96
includes taxes & fees
May 18 - May 19
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,001 reviews)
"Courteous desk"

Reviewed on Apr 24, 2025

Quality Inn West Springfield
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
The price is $116 per night from Jun 1 to Jun 2
$116
includes taxes & fees
Jun 1 - Jun 2
Stay at this hotel in South Deerfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
7.2/10 Good! (1,000 reviews)
"The carpeted area around the beds were very dirty, but the bed and bath linens seemed clean. The heat/cool worked fine and tv options were better than some hotels. We had several issues with our key cards not working, but staff was friendly and fixed the issues right away. Definitely better than ..."

Reviewed on Apr 28, 2025

Red Roof Inn PLUS+ South Deerfield – Amherst
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
The price is $155 per night from May 4 to May 5
$155
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (667 reviews)
"We love staying here every time we visit Smith"

Reviewed on Apr 28, 2025

The Ellery
Candlewood Suites West Springfield by IHG
Candlewood Suites West Springfield by IHG
2.5 out of 5
572 Riverdale St, West Springfield, MA
The price is $113 per night from Jun 1 to Jun 2
$113
includes taxes & fees
Jun 1 - Jun 2
Book a stay at this business-friendly hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff ...
8.2/10 Very Good! (688 reviews)
"Clean ..comfortable and close to highway..affordable"

Reviewed on Apr 27, 2025

Candlewood Suites West Springfield by IHG
Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield
2.5 out of 5
440 Memorial Dr, Chicopee, MA
The price is $115 per night from May 26 to May 27
$115
includes taxes & fees
May 26 - May 27
Stay at this hotel in Chicopee. 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! (1,004 reviews)
Nice place
"Beds were comfy, rooms were nice and clean. Love the soap and hair product dispensers in the bathroom."

Reviewed on Apr 27, 2025

Tru by Hilton Chicopee Springfield
See all 458 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.