Search Cheap Flights to
Chestnut Hill

Name: Harborside Inn Of Boston
Rating: 9

The 18th hole of the Open Course at The Country Club

Photo by Ed Gaffny

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Chestnut Hill Flights as Low as $103

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

All deals

One way

Roundtrip

Mon, Jun 9 - Sat, Jun 14

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$103

Roundtrip

found 3 hours ago

Wed, Aug 27 - Wed, Sep 3

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$128

Roundtrip

found 11 hours ago

Mon, Jun 9 - Sat, Jun 14

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$133

Roundtrip

found 3 hours ago

Mon, Jun 23 - Sat, Jun 28

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$134

Roundtrip

found 3 days ago

Tue, Jun 10 - Wed, Jun 11

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$139

Roundtrip

found 18 hours ago

Mon, Jun 9 - Sat, Jun 14

FLL

Fort Lauderdale - Hollywood Intl.

BOS

Logan Intl.

$140

Roundtrip

found 3 hours ago

Fri, Jun 6 - Tue, Jun 10

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$153

Roundtrip

found 1 day ago

Sat, Aug 2 - Tue, Aug 12

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$157

Roundtrip

found 22 hours ago

Tue, Aug 19 - Tue, Aug 26

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$157

Roundtrip

found 1 day ago

Mon, Jun 30 - Fri, Aug 29

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$159

Roundtrip

found 17 hours ago

Tue, Aug 19 - Tue, Aug 26

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$172

Roundtrip

found 1 day ago

Tue, Aug 19 - Tue, Aug 26

ATL

Hartsfield-Jackson Atlanta Intl.

BOS

Logan Intl.

$177

Roundtrip

found 1 day ago

Fri, Oct 31 - Fri, Oct 31

LAX

Los Angeles Intl.

BOS

Logan Intl.

$179

Roundtrip

found 2 days ago

Thu, Jun 5 - Sat, Jun 7

LAX

Los Angeles Intl.

BOS

Logan Intl.

$319

Roundtrip

found 4 days ago

Tue, Jun 17 - Wed, Jun 25

LAX

Los Angeles Intl.

BOS

Logan Intl.

$372

Roundtrip

found 16 hours ago

Sat, Jun 14 - Mon, Jun 30

LAX

Los Angeles Intl.

BOS

Logan Intl.

$393

Roundtrip

found 3 days ago

Cheap Flights to Chestnut Hill

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

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

Frequently Asked Questions About flights to Chestnut Hill

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chestnut Hill 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 BOS airport.

What is the cheapest month to fly to Chestnut Hill?

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 Chestnut Hill are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chestnut Hill?

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 Chestnut Hill.

What airport is best to fly into Chestnut Hill?

When you’re planning your trip to Chestnut Hill, convenience is the name of the game. Luckily, Chestnut Hill Boston Harbor Seaplane Base Airport is nearby so you can deplane and get going on checking off everything on your Chestnut Hill must-do list.

How much are flights to Chestnut Hill?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chestnut Hill on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $103, 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 Chestnut Hill?

The trick to saving a stack of cash on your flight to Chestnut Hill? 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 $103 right now, why wait?

Chestnut Hill Flight Information
Destination airport	Portsmouth Intl.
Destination airport IATA code	PSM
Roundtrip price	$101

Last Minute Hotel Deals in Chestnut Hill

YOTEL Boston

65 Seaport Blvd, Boston, MA

Stay at this 4-star hotel in Boston. Enjoy free WiFi, 2 bars/lounges, and a rooftop terrace. Our guests praise the restaurant and the bar in our reviews. Popular ...

8.4/10 Very Good! (2,031 reviews)

"Even though the rooms are small they are quite utilitarian and comfortable."

Reviewed on May 22, 2025

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Four Points by Sheraton Boston Newton

320 Washington Street, Newton, MA

Book a stay at this business-friendly hotel in Newton. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...

8.2/10 Very Good! (2,858 reviews)

"Y"

Reviewed on May 26, 2025

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The Dagny Boston

89 Broad Street, Boston, MA

Stay at this 4-star luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the restaurant in our ...

9.2/10 Wonderful! (5,846 reviews)

"Beautiful property with helpful staff. Comfortable beds! We loved our stay and can’t wait to go back!"

Reviewed on May 21, 2025

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Hilton Boston Park Plaza

50 Park Plaza, Boston, MA

Book a stay at this historic hotel in Boston. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the bar and the helpful staff ...

8.2/10 Very Good! (3,273 reviews)

"I have often stayed here. It is a dependable hotel, that is very welcoming to its guests."

Reviewed on May 21, 2025

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The Revolution Hotel

40 Berkeley Street, Boston, MA

Stay at this 3.5-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful ...

8.8/10 Excellent! (2,034 reviews)

"Great hotel. Optimal location in Boston, especially for the price. The room with the bathroom down the hall is worth the price cut."

Reviewed on May 23, 2025

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citizenM Boston Back Bay

408 Newbury street, Boston, MA

Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Popular attractions Fenway Park and Copley Square ...

9.4/10 Exceptional! (1,177 reviews)

"The view overlooking Massachusetts avenue was perfect! Would for sure stay here again"

Reviewed on May 23, 2025

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Omni Boston Hotel at the Seaport

450 Summer Street, Boston, MA

Stay at this 4-star spa hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...

9/10 Wonderful! (3,445 reviews)

"I love staying here but this time i had the DND on the door and housekeeping was pounding on the door at 9am"

Reviewed on May 22, 2025

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Harborside Inn Of Boston

185 State St, Boston, MA

Stay at this 4-star hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour front desk. Our guests praise the breakfast and the restaurant in ...

9/10 Wonderful! (5,151 reviews)

"1st room’s air conditioner did not work. Staff were quick to move us to a more suitable room."

Reviewed on May 22, 2025

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See all 3,553 properties in Chestnut Hill

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.

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