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Brookline

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Brookline Flights as Low as $127

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

Breeze Airways
Thu, Nov 19 - Thu, Dec 10
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Nov 19 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Dec 10, priced at $127 found 11 hours ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$130 Roundtrip, found 1 day ago
$130
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $130 found 1 day ago
Breeze Airways
Thu, Nov 19 - Thu, Dec 10
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Nov 19 from Raleigh - Durham Intl. to Portsmouth Intl., returning Thu, Dec 10, priced at $132 found 11 hours ago
Frontier Airlines
Mon, Aug 10 - Sat, Aug 29
MCO
Orlando Intl.
BOS
Logan Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Aug 10 from Orlando Intl. to Logan Intl., returning Sat, Aug 29, priced at $133 found 5 days ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$135 Roundtrip, found 1 day ago
$135
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $135 found 1 day ago
Frontier Airlines
Wed, Aug 12 - Sat, Aug 29
MCO
Orlando Intl.
BOS
Logan Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Logan Intl., returning Sat, Aug 29, priced at $137 found 3 days ago
Frontier Airlines
Sat, Aug 29 - Sat, Sep 5
MCO
Orlando Intl.
BOS
Logan Intl.
$139 Roundtrip, found 4 hours ago
$139
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Logan Intl., returning Sat, Sep 5, priced at $139 found 4 hours ago
Breeze Airways
Sun, Aug 30 - Sun, Sep 6
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$140 Roundtrip, found 1 day ago
$140
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Sep 6, priced at $140 found 1 day ago
Breeze Airways
Sun, Aug 30 - Sun, Aug 30
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$140 Roundtrip, found 5 days ago
$140
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sun, Aug 30 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Aug 30, priced at $140 found 5 days ago
Frontier Airlines
Tue, Aug 11 - Thu, Aug 13
MCO
Orlando Intl.
BOS
Logan Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Aug 11 from Orlando Intl. to Logan Intl., returning Thu, Aug 13, priced at $142 found 2 days ago
Frontier Airlines
Thu, Aug 27 - Mon, Aug 31
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$160 Roundtrip, found 5 days ago
$160
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Aug 27 from Raleigh - Durham Intl. to Logan Intl., returning Mon, Aug 31, priced at $160 found 5 days ago
Breeze Airways
Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$185 Roundtrip, found 2 days ago
$185
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Portsmouth Intl., returning Sun, Dec 13, priced at $185 found 2 days ago
United
Fri, Aug 21 - Sun, Aug 23
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$193 Roundtrip, found 10 hours ago
$193
Roundtrip
found 10 hours ago
Select United flight, departing Fri, Aug 21 from Raleigh - Durham Intl. to Logan Intl., returning Sun, Aug 23, priced at $193 found 10 hours ago
Delta
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando Intl.
BOS
Logan Intl.
$199 Roundtrip, found 4 hours ago
$199
Roundtrip
found 4 hours ago
Select Delta flight, departing Wed, Sep 2 from Orlando Intl. to Logan Intl., returning Wed, Sep 9, priced at $199 found 4 hours ago
American Airlines
Wed, Aug 26 - Tue, Sep 15
MCO
Orlando Intl.
BOS
Logan Intl.
$202 Roundtrip, found 5 days ago
$202
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Logan Intl., returning Tue, Sep 15, priced at $202 found 5 days ago
JetBlue Airways
Tue, Oct 27 - Tue, Oct 27
RDU
Raleigh - Durham Intl.
BOS
Logan Intl.
$232 Roundtrip, found 2 days ago
$232
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Tue, Oct 27 from Raleigh - Durham Intl. to Logan Intl., returning Tue, Oct 27, priced at $232 found 2 days ago

Cheap Flights to Brookline

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

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

Frequently Asked Questions About flights to Brookline

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

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 Brookline are in November, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Brookline?

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 Brookline.

What airport is best to fly into Brookline?

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

How much are flights to Brookline?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Brookline on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $127, 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 Brookline?

The trick to saving a stack of cash on your flight to Brookline? 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 $127 right now, why wait?

Brookline Flight Information
Destination airport
Portsmouth Intl.
Destination airport IATA code
PSM
Roundtrip price
$126

Last Minute Hotel Deals in Brookline

Arcadian Hotel

Arcadian Hotel

3.5 out of 5
1200 Beacon St Brookline MA
Stay at this hotel in Brookline. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our ...
8/10 Very Good! (4,310 reviews)
"The only thing I liked about this hotel was its location. It was very convenient to get anywhere in the city. Unfortunately, that’s where the positives end. The room windows faced the hallway, so everyone walking by could look directly into our room. It felt like living in a zoo behind glass, with ..."

Reviewed on Jul 10, 2026

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Arcadian Hotel
Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Book a stay at this business-friendly hotel in Boston. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the breakfast and the restaurant ...
9.6/10 Exceptional! (4,552 reviews)
"The staff was really nice and helpful! They had umbrellas ready as soon as the rain started picking up."

Reviewed on Jul 10, 2026

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Seaport Hotel Boston
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
575 Memorial Drive Cambridge MA
Book a stay at this business-friendly hotel in Cambridge. Enjoy free WiFi, breakfast (surcharge), and a 24-hour health club. Our guests praise the restaurant ...
9/10 Wonderful! (2,436 reviews)
"The property was located in a nice quiet area for a city hotel. The view was nice by the water and the balcony was comfortable for outdoors dining. The rooms was not as big as we expected, especially traveling with teens. The room was designed with a lot of wasted space. The room AC unit was not ..."

Reviewed on Jul 10, 2026

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Hyatt Regency Boston/Cambridge
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in ...
9/10 Wonderful! (2,732 reviews)
"The room was very clean. We didn’t know about the shared bathrooms but I have to say the staff kept them very clean. They were there several times a day. They gave us robes, towels, soap…. in a bag. Very convenient. It was a little far though from the downtown area. We didn’t have Uber."

Reviewed on Jul 10, 2026

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The Revolution Hotel
The Langham, Boston

The Langham, Boston

5 out of 5
250 Franklin St Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
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The Langham, Boston
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Stay at this hotel in Boston. Enjoy free WiFi, a 24-hour front desk, and a business center. Our guests praise the breakfast and the restaurant in our reviews. ...
9.2/10 Wonderful! (6,826 reviews)
"The room was well appointed. Bathroom finishes were tile everywhere up to the wainscot. Plenty of counter space. Good lighting. Bedside furniture, lights, and electrical plugs were perfect. Completely solid construction. Well placed and permanently installed bedside lantern with a dimmer switch conveniently ..."

Reviewed on Jul 10, 2026

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Harborside Inn Of Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Book a stay at this luxury hotel in Boston. Enjoy free WiFi, a full-service spa, and 4 restaurants. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (4,798 reviews)
"It’s our kids first trip to America, and our first stop is Boston. I’m so relieved that Omni has exceeded our expectations in every possible way of not more. We had the best time in Boston. Start with the check-in: straight forward, easy check in with helpful staff at the front. Plus complimentary ..."

Reviewed on Jul 10, 2026

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Omni Boston Hotel at the Seaport
The Midtown Hotel MOD Collection by Sonesta

The Midtown Hotel MOD Collection by Sonesta

3 out of 5
220 Huntington Avenue Boston MA
Stay at this hotel in Boston. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Copley Square and Fenway Park are located nearby.
8.2/10 Very Good! (594 reviews)
"Clean room, but little to no complimentary breakfast. Very disappointing."

Reviewed on Jul 10, 2026

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The Midtown Hotel MOD Collection by Sonesta
See all 4,254 properties in Brookline
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.