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Chester

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Chester Flights as Low as $97

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

Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $97 found 1 day ago
Spirit Airlines
Fri, Sep 5 - Fri, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 15 hours ago
$98
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, Sep 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Sep 12, priced at $98 found 15 hours ago
Spirit Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $100 found 1 hour ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$103 Roundtrip, found 5 hours ago
$103
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $103 found 5 hours ago
Frontier Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$105 Roundtrip, found 1 hour ago
$105
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $105 found 1 hour ago
Spirit Airlines
Mon, Oct 27 - Fri, Oct 31
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 2 days ago
$108
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Oct 27 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Oct 31, priced at $108 found 2 days ago
Frontier Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$110 Roundtrip, found 1 hour ago
$110
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $110 found 1 hour ago
JetBlue Airways
Sat, Oct 18 - Mon, Oct 20
TPA
Tampa Intl.
BDL
Bradley Intl.
$111 Roundtrip, found 5 days ago
$111
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Oct 18 from Tampa Intl. to Bradley Intl., returning Mon, Oct 20, priced at $111 found 5 days ago
Breeze Airways
Fri, Aug 29 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$112 Roundtrip, found 6 days ago
$112
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Aug 29 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $112 found 6 days ago
JetBlue Airways
Fri, Sep 19 - Sat, Sep 20
TPA
Tampa Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Sep 19 from Tampa Intl. to Bradley Intl., returning Sat, Sep 20, priced at $138 found 5 days ago
American Airlines
Thu, Aug 28 - Fri, Aug 29
MCO
Orlando Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 5 days ago
$161
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Fri, Aug 29, priced at $161 found 5 days ago
JetBlue Airways
Wed, Aug 20 - Mon, Aug 25
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$186 Roundtrip, found 1 day ago
$186
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Aug 20 from Southwest Florida Intl. to Bradley Intl., returning Mon, Aug 25, priced at $186 found 1 day ago
United
Fri, Sep 5 - Fri, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 15 hours ago
$190
Roundtrip
found 15 hours ago
Select United flight, departing Fri, Sep 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Sep 12, priced at $190 found 15 hours ago
Delta
Tue, Sep 9 - Tue, Sep 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Sep 9 from Orlando Intl. to Bradley Intl., returning Tue, Sep 9, priced at $197 found 1 day ago
JetBlue Airways
Sat, Oct 4 - Wed, Oct 15
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$268 Roundtrip, found 5 days ago
$268
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Oct 4 from Luis Munoz Marin Intl. to Bradley Intl., returning Wed, Oct 15, priced at $268 found 5 days ago
Spirit Airlines
Thu, Sep 25 - Mon, Sep 29
SAT
San Antonio Intl.
BDL
Bradley Intl.
$270 Roundtrip, found 2 days ago
$270
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Sep 25 from San Antonio Intl. to Bradley Intl., returning Mon, Sep 29, priced at $270 found 2 days ago

Cheap Flights to Chester

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

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

Frequently Asked Questions About flights to Chester

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

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 Chester are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

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 Chester.

What airport is best to fly into Chester?

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

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $97, 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 Chester?

The trick to saving a stack of cash on your flight to Chester? 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 $97 right now, why wait?

Chester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$96

Last Minute Hotel Deals in Chester

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (555 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on Aug 11, 2025

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Berkshire Mountain Lodge
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! (1,002 reviews)
"My daughter and the kids said it was perfect for their overnight stay after visiting Six Flags."

Reviewed on Aug 7, 2025

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Quality Inn West Springfield
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street, Springfield, MA
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,274 reviews)
"N/A"

Reviewed on Aug 8, 2025

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La Quinta Inn & Suites by Wyndham Springfield MA
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! (2,232 reviews)
"We have stayed here several times now. It is our go to for the area! We love the rooms and the breakfast is excellent!"

Reviewed on Aug 11, 2025

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D. Hotel Suites & Spa
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (766 reviews)
"The bathroom in our room looks like someone was murdered in the bathtub. There were stains on the bottom of the tub."

Reviewed on Aug 10, 2025

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FairBridge Inn Express
Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

2.5 out of 5
440 Memorial Dr, Chicopee, MA
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! (1,000 reviews)
"Staff is wonderful & attentive."

Reviewed on Aug 9, 2025

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Tru by Hilton Chicopee Springfield
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 Big E and Eastern States Exposition are ...
5.8/10 (999 reviews)
"Good"

Reviewed on Aug 5, 2025

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Riverdale Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (668 reviews)
"The room was fine, quiet and clean. It was somewhat small. This is a nicely refurbished old standard motel. The lobby area was very nice but the location is high atop a hill off of a major road. You can’t walk anywhere from the hotel and it can be difficult making a left turn into it."

Reviewed on Aug 7, 2025

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Berkshires Untold
See all 836 properties in Chester
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.