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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, Sep 17 - Wed, Sep 17
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$102 Roundtrip, found 14 hours ago
$102
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Wed, Sep 17 from Orlando Intl. to Portsmouth Intl., returning Wed, Sep 17, priced at $102 found 14 hours ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $107 found 1 day ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 6 hours ago
$108
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $108 found 6 hours ago
Spirit Airlines
Tue, Jul 8 - Fri, Jul 11
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$108 Roundtrip, found 1 day ago
$108
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Fri, Jul 11, priced at $108 found 1 day ago
Spirit Airlines
Sat, Nov 15 - Mon, Nov 17
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 14 hours ago
$108
Roundtrip
found 14 hours ago
Select Spirit Airlines flight, departing Sat, Nov 15 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 17, priced at $108 found 14 hours ago
Breeze Airways
Wed, Dec 3 - Sat, Dec 6
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 1 day ago
$112
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Dec 6, priced at $112 found 1 day ago
Breeze Airways
Fri, Aug 1 - Mon, Aug 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$113 Roundtrip, found 6 hours ago
$113
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Aug 1 from Orlando Intl. to Bradley Intl., returning Mon, Aug 4, priced at $113 found 6 hours ago
Breeze Airways
Wed, Oct 22 - Wed, Oct 22
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$117 Roundtrip, found 1 day ago
$117
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Oct 22 from Orlando Intl. to Portsmouth Intl., returning Wed, Oct 22, priced at $117 found 1 day ago
Spirit Airlines
Mon, Jun 30 - Tue, Jul 8
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Jun 30 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Jul 8, priced at $121 found 1 day ago
Spirit Airlines
Mon, Sep 15 - Sat, Sep 20
MCO
Orlando Intl.
BOS
Logan Intl.
$130 Roundtrip, found 6 hours ago
$130
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Mon, Sep 15 from Orlando Intl. to Logan Intl., returning Sat, Sep 20, priced at $130 found 6 hours ago
Delta
Wed, Sep 3 - Tue, Sep 9
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Sep 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Sep 9, priced at $137 found 16 hours ago
JetBlue Airways
Wed, Sep 3 - Tue, Sep 9
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Wed, Sep 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Sep 9, priced at $137 found 16 hours ago
Frontier Airlines
Sat, Jul 5 - Sat, Jul 12
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$157 Roundtrip, found 22 hours ago
$157
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Sat, Jul 5 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, Jul 12, priced at $157 found 22 hours ago
Frontier Airlines
Sat, Jul 12 - Mon, Jul 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jul 12 from Orlando Intl. to Bradley Intl., returning Mon, Jul 14, priced at $157 found 1 day ago
American Airlines
Wed, Sep 3 - Tue, Sep 9
FLL
Fort Lauderdale - Hollywood Intl.
BOS
Logan Intl.
$159 Roundtrip, found 16 hours ago
$159
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Wed, Sep 3 from Fort Lauderdale - Hollywood Intl. to Logan Intl., returning Tue, Sep 9, priced at $159 found 16 hours ago
United
Tue, Aug 19 - Tue, Aug 26
ATL
Hartsfield-Jackson Atlanta Intl.
BOS
Logan Intl.
$182 Roundtrip, found 13 hours ago
$182
Roundtrip
found 13 hours ago
Select United flight, departing Tue, Aug 19 from Hartsfield-Jackson Atlanta Intl. to Logan Intl., returning Tue, Aug 26, priced at $182 found 13 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 September, 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 $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
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$101

Last Minute Hotel Deals in Chesterfield

Red Roof Inn PLUS+ West Springfield
Red Roof Inn PLUS+ West Springfield
2.5 out of 5
1254 Riverdale Street, West Springfield, MA
Stay at this hotel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,001 reviews)
"Amazing space clean and well maintained"

Reviewed on Jun 10, 2025

Get rates
Red Roof Inn PLUS+ West Springfield
D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
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! (2,268 reviews)
"It was the perfect stay for our family for a night! It was so clean, everyone was kind, the breakfast was AMAZING & so was the indoor pool! Highly recommend!"

Reviewed on Jun 15, 2025

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D. Hotel Suites & Spa
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
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! (1,009 reviews)
"I like everything cleanness, pool,staff especially very professional, cleanness of room,plus quiet ,ac runs great"

Reviewed on Jun 16, 2025

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Quality Inn West Springfield
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
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! (710 reviews)
"Very comfortable"

Reviewed on Jun 14, 2025

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The Ellery
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
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 ...
7/10 Good! (1,005 reviews)
"Great room. Very clean and accommodating."

Reviewed on Jun 15, 2025

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Red Roof Inn PLUS+ South Deerfield – Amherst
Riverdale Inn
Riverdale Inn
2 out of 5
1500 Riverdale Street, On Route 5, West Springfield, MA
Stay at this motel in West Springfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions MGM Springfield and Naismith Memorial Basketball ...
5.8/10 (1,000 reviews)
"I like the quiet covenant"

Reviewed on Jun 15, 2025

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Riverdale Inn
Hotel UMass
Hotel UMass
2.5 out of 5
1 Campus Center Way, Amherst, MA
Stay at this hotel in Amherst. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Mullins ...
8.6/10 Excellent! (975 reviews)
"Great staff at check in, property was very clean and the rooms were really nice and fairly new remodeling!!"

Reviewed on Jun 16, 2025

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Hotel UMass
Quality Inn & Suites Northampton - Amherst
Quality Inn & Suites Northampton - Amherst
2.5 out of 5
117 Conz St, Northampton, MA
Book a stay at this business-friendly hotel in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7/10 Good! (1,004 reviews)
"The room was clean and large. They do need to have a luggage rack for suitcases because the only place to put and open a suitcase was on the floor! Not good for seniors!"

Reviewed on Jun 14, 2025

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Quality Inn & Suites Northampton - Amherst
See all 463 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.