Search Cheap Flights to
Chestnut Hill

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Chestnut Hill Flights as Low as $92

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

JetBlue Airways
Wed, Apr 16 - Wed, Apr 16
ORD
O'Hare Intl.
BOS
Logan Intl.
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Apr 16 from O'Hare Intl. to Logan Intl., returning Wed, Apr 16, priced at $92 found 3 days ago
JetBlue Airways
Sat, May 3 - Tue, May 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, May 3 from O'Hare Intl. to Logan Intl., returning Tue, May 6, priced at $97 found 1 day ago
American Airlines
Fri, Apr 4 - Mon, Apr 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Apr 4 from O'Hare Intl. to Logan Intl., returning Mon, Apr 7, priced at $97 found 6 days ago
United
Wed, Apr 2 - Sat, Apr 5
ORD
O'Hare Intl.
BOS
Logan Intl.
$97 Roundtrip, found 5 days ago
$97
Roundtrip
found 5 days ago
Select United flight, departing Wed, Apr 2 from O'Hare Intl. to Logan Intl., returning Sat, Apr 5, priced at $97 found 5 days ago
Delta
Sat, May 3 - Sat, May 3
ORD
O'Hare Intl.
BOS
Logan Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, May 3 from O'Hare Intl. to Logan Intl., returning Sat, May 3, priced at $97 found 1 day ago
Delta
Tue, May 6 - Sat, May 10
ORD
O'Hare Intl.
BOS
Logan Intl.
$98 Roundtrip, found 4 days ago
$98
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, May 6 from O'Hare Intl. to Logan Intl., returning Sat, May 10, priced at $98 found 4 days ago
JetBlue Airways
Fri, Apr 4 - Sun, Apr 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Fri, Apr 4 from O'Hare Intl. to Logan Intl., returning Sun, Apr 6, priced at $107 found 2 days ago
Delta
Fri, Apr 4 - Sun, Apr 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Apr 4 from O'Hare Intl. to Logan Intl., returning Sun, Apr 6, priced at $107 found 2 days ago
JetBlue Airways
Wed, May 7 - Fri, May 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, May 7 from O'Hare Intl. to Logan Intl., returning Fri, May 9, priced at $117 found 4 days ago
JetBlue Airways
Tue, May 6 - Fri, May 9
ORD
O'Hare Intl.
BOS
Logan Intl.
$117 Roundtrip, found 4 days ago
$117
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Tue, May 6 from O'Hare Intl. to Logan Intl., returning Fri, May 9, priced at $117 found 4 days ago
Delta
Wed, Apr 2 - Mon, Apr 14
ORD
O'Hare Intl.
BOS
Logan Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 2 from O'Hare Intl. to Logan Intl., returning Mon, Apr 14, priced at $118 found 2 days ago
United
Fri, Apr 4 - Mon, Apr 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Select United flight, departing Fri, Apr 4 from O'Hare Intl. to Logan Intl., returning Mon, Apr 7, priced at $120 found 6 days ago
Spirit Airlines
Sun, Apr 20 - Wed, Apr 23
SAT
San Antonio Intl.
BOS
Logan Intl.
$175 Roundtrip, found 15 hours ago
$175
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Sun, Apr 20 from San Antonio Intl. to Logan Intl., returning Wed, Apr 23, priced at $175 found 15 hours ago
Hawaiian Airlines
Wed, Apr 9 - Wed, May 28
SFO
San Francisco Intl.
BOS
Logan Intl.
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Wed, Apr 9 from San Francisco Intl. to Logan Intl., returning Wed, May 28, priced at $199 found 3 days ago
Alaska Airlines
Thu, Apr 10 - Wed, May 28
SFO
San Francisco Intl.
BOS
Logan Intl.
$218 Roundtrip, found 3 days ago
$218
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Thu, Apr 10 from San Francisco Intl. to Logan Intl., returning Wed, May 28, priced at $218 found 3 days ago
Frontier Airlines
Sun, May 4 - Thu, May 8
SFO
San Francisco Intl.
BOS
Logan Intl.
$249 Roundtrip, found 1 hour ago
$249
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, May 4 from San Francisco Intl. to Logan Intl., returning Thu, May 8, priced at $249 found 1 hour 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 April, 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 $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 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 $92 right now, why wait?

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

Last Minute Hotel Deals in Chestnut Hill

citizenM Boston Back Bay
citizenM Boston Back Bay
4 out of 5
408 Newbury street, Boston, MA
The price is $185 per night from Mar 30 to Mar 31
$185
includes taxes & fees
Mar 30 - Mar 31
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! (903 reviews)
"Transit station right across street. Staff very helpful in suggesting restaurants"

Reviewed on Mar 26, 2025

citizenM Boston Back Bay
Seaport Hotel Boston
Seaport Hotel Boston
4 out of 5
1 Seaport Lane, Boston, MA
The price is $347 per night from Apr 11 to Apr 12
$347
includes taxes & fees
Apr 11 - Apr 12
Stay at this 4-star eco-certified hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.4/10 Exceptional! (2,860 reviews)
"Excellent location, friendly and accommodating staff."

Reviewed on Mar 28, 2025

Seaport Hotel Boston
Harborside Inn Of Boston
Harborside Inn Of Boston
4 out of 5
185 State St, Boston, MA
The price is $174 per night from Mar 30 to Mar 31
$174
includes taxes & fees
Mar 30 - Mar 31
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! (4,960 reviews)
"The property is decently maintained, and the staff is absolutely friendly, attentive and professional. The property could use some updating as far as the rooms, i.e., lumpy mattress, cracked tiles in bathroom. The bathrooms in the common area are located in the basement and you are introduced to ..."

Reviewed on Mar 28, 2025

Harborside Inn Of Boston
The Revolution Hotel
The Revolution Hotel
3.5 out of 5
40 Berkeley Street, Boston, MA
The price is $177 per night from Mar 30 to Mar 31
$177
includes taxes & fees
Mar 30 - Mar 31
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 ...
8.6/10 Excellent! (1,973 reviews)
Nice Surprise
"Great experience. The hotel was in an authentic Boston location near the subway and copley square. the lobby was inviting and sold good coffee. The front staff were helpful, kind and answered all of my annoying questions. I had to cut short my trip and the hotel has a policy to refund you if you ..."

Reviewed on Mar 25, 2025

The Revolution Hotel
Omni Boston Hotel at the Seaport
Omni Boston Hotel at the Seaport
4 out of 5
450 Summer Street, Boston, MA
The price is $289 per night from Apr 18 to Apr 19
$289
includes taxes & fees
Apr 18 - Apr 19
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! (3,340 reviews)
"Access to Convention Center is perfect! Great Sports Bar! Very Modern! Too many things did not have real people staffing them. I dislike ordering off aps or going in a convenience store with no one there to discuss items with. Room was way too small. I appreciate the desire to be green, but no closets, ..."

Reviewed on Mar 28, 2025

Omni Boston Hotel at the Seaport
The Godfrey Hotel Boston
The Godfrey Hotel Boston
4 out of 5
505 Washington Street, Boston, MA
The price is $224 per night from Mar 30 to Mar 31
$224
includes taxes & fees
Mar 30 - Mar 31
Stay at this 4-star boutique hotel in Boston. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the ...
9.4/10 Exceptional! (3,831 reviews)
"We would definitely stay here again! The staff is friendly and the location is great."

Reviewed on Mar 28, 2025

The Godfrey Hotel Boston
citizenM Boston North Station
citizenM Boston North Station
4 out of 5
80-120 Causeway Street, Boston, MA
The price is $162 per night from Mar 30 to Mar 31
$162
includes taxes & fees
Mar 30 - Mar 31
Stay at this 4-star business-friendly hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
9.2/10 Wonderful! (3,241 reviews)
"This hotel is perfect for a single traveler or a couple. The room is small but it has everything you need. It is also very modern, and an iPad controls everything in the room including lights, temperature, tv and blinds. Highly recommend!"

Reviewed on Mar 28, 2025

citizenM Boston North Station
The Dagny Boston
The Dagny Boston
4 out of 5
89 Broad Street, Boston, MA
The price is $202 per night from Mar 30 to Mar 31
$202
includes taxes & fees
Mar 30 - Mar 31
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! (5,606 reviews)
Great hotel, nice experience
"Great hotel, great experience highly recommend good location"

Reviewed on Mar 28, 2025

The Dagny Boston
See all 3,562 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.