Cheap flights To Brookline (BOS) from $57

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Cheap Flights to Brookline from $57 One Way, $110 Round Trip

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

Thu, Jan 21 - Sun, Jan 24
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $110 found 2 days ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$112 Roundtrip, found 5 days ago
$112
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $112 found 5 days ago
Sat, Oct 3 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$113 Roundtrip, found 5 days ago
$113
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Sat, Oct 3 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $113 found 5 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $118 just found
Thu, Jan 21 - Sun, Jan 24
RDU
Raleigh - Durham Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 16 hours ago
$122
Roundtrip
found 16 hours ago
Select Breeze Airways flight, departing Thu, Jan 21 from Raleigh - Durham Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $122 found 16 hours ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 13 hours ago
$122
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $122 found 13 hours ago
Thu, Jan 21 - Sun, Jan 24
SFB
Orlando Sanford Intl.
PSM
Portsmouth Intl.
$122 Roundtrip, found 12 hours ago
$122
Roundtrip
found 12 hours ago
Select Allegiant Air flight, departing Thu, Jan 21 from Orlando Sanford Intl. to Portsmouth Intl., returning Sun, Jan 24, priced at $122 found 12 hours ago
Sat, Oct 31 - Sat, Nov 7
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$123 Roundtrip, found 13 hours ago
$123
Roundtrip
found 13 hours ago
Select Breeze Airways flight, departing Sat, Oct 31 from Orlando Intl. to Portsmouth Intl., returning Sat, Nov 7, priced at $123 found 13 hours ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
BOS
Logan Intl.
$126 Roundtrip, found 4 days ago
$126
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Orlando Intl. to Logan Intl., returning Sat, Oct 31, priced at $126 found 4 days ago
Sat, Oct 24 - Sat, Oct 31
MCO
Orlando Intl.
PSM
Portsmouth Intl.
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 24 from Orlando Intl. to Portsmouth Intl., returning Sat, Oct 31, priced at $128 found 1 day ago

Brookline Flight Information

Traveling To
Brookline
Destination Airport IATA Code
BOS
Number of Airlines Serving
Airlines
Breeze Airways, Allegiant Air, Frontier Airlines
Flight Price
$110
Earliest Departing Flight
Latest Departing Flight

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Brookline economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Bell Inn
5.0-star property

The Bell Inn

Nov 2 - Nov 5

3 night stay

Los Angeles (LAX) to Boston (BOS)

Southwest Airlines • Non-stop roundtrip • Coach
Price was $703, price is now $525 per person
$525
per person
found 16 hours ago
Furnished Apartment Near Longwood
3.0-star property

Furnished Apartment Near Longwood

Oct 20 - Oct 23

3 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Coach
Price was $1,207, price is now $880 per person
$880
per person
found 1 day ago
Market Square Inn
2.0-star property

Market Square Inn

Oct 23 - Oct 26

3 night stay

Dallas (DFW) to Boston (BOS)

Southwest Airlines • Non-stop • Coach

Boston (BOS) to Dallas (DFW)

Frontier Airlines • Non-stop • Coach
Price was $1,596, price is now $1,178 per person
$1,178
per person
found 24 hours ago
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Brookline premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Omni Parker House
4.5-star property

Omni Parker House

9/10 Wonderful! (3,703 reviews)

Oct 31 - Nov 2

2 night stay

San Juan (SJU) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,023, price is now $898 per person
$898
per person
found 1 day ago
Stayed 2 nights. Great location for sightseeing. Pretty spendy, but that seems to be the case for all hotels in downtown Boston. No coffee in room or in lobby for guests, and no microwaves in rooms. Wished they provided those amenities. We had a bizarre encounter with 3 young men at 11 pm “ghost hunting” in our hallway banging on our door. We called security and they came immediately and escorted them out. Kudos for an excellent security team.

Reviewed on Sep 15, 2026

Eurostars The Boxer
4.0-star property

Eurostars The Boxer

8.8/10 Excellent! (1,588 reviews)

Oct 31 - Nov 2

2 night stay

San Juan (SJU) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,049, price is now $924 per person
$924
per person
found 1 day ago
So comfy and comfortable, I loved it.

Reviewed on Sep 14, 2026

Comfort Inn Randolph - Boston
2.5-star property

Comfort Inn Randolph - Boston

7.8/10 Good! (1,005 reviews)

Nov 6 - Nov 9

3 night stay

Phoenix (PHX) to Boston (BOS)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,162, price is now $1,000 per person
$1,000
per person
found 1 day ago
Our stay was wonderful. We had a fast check in experience. Our room was very clean and the ac worked great. The bed was extremely comfortable and felt like sleeping in a cloud. Breakfast was wonderful and there were plenty of food options. We would definitely stay again.

Reviewed on Sep 15, 2026

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Brookline business class flight packages

Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel
4.5-star property

The Atlas Hotel

9.4/10 Exceptional! (333 reviews)

Oct 15 - Oct 19

4 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • BusinessClass

Boston (BOS) to Los Angeles (LAX)

American Airlines • Non-stop • BusinessClass
Price was $3,553, price is now $2,945 per person
$2,945
per person
found 9 hours ago
The room is quite small and it’s nit as advertised as a luxury hotel.

Reviewed on Sep 14, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,014 reviews)

Oct 15 - Oct 19

4 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • BusinessClass

Boston (BOS) to Los Angeles (LAX)

American Airlines • Non-stop • BusinessClass
Price was $4,436, price is now $3,553 per person
$3,553
per person
found 9 hours ago
What a great hotel

Reviewed on Sep 13, 2026

Hotel AKA Boston Common
4.0-star property

Hotel AKA Boston Common

9/10 Wonderful! (1,773 reviews)

Oct 15 - Oct 19

4 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • BusinessClass

Boston (BOS) to Los Angeles (LAX)

American Airlines • Non-stop • BusinessClass
Price was $4,587, price is now $3,782 per person
$3,782
per person
found 9 hours ago
Hotel was great ! Excellent vibes !

Reviewed on Sep 15, 2026

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See all available trips from Los Angeles to Brookline
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Brookline first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel
4.5-star property

The Atlas Hotel

9.4/10 Exceptional! (333 reviews)

Oct 16 - Oct 21

5 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • FirstClass

Boston (BOS) to Los Angeles (LAX)

American Airlines • Non-stop • FirstClass
Price was $3,504, price is now $2,769 per person
$2,769
per person
found 9 hours ago
The room is quite small and it’s nit as advertised as a luxury hotel.

Reviewed on Sep 14, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,014 reviews)

Oct 15 - Oct 19

4 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • FirstClass

Boston (BOS) to Los Angeles (LAX)

Delta • Non-stop • FirstClass
Price was $4,288, price is now $3,311 per person
$3,311
per person
found 1 day ago
What a great hotel

Reviewed on Sep 13, 2026

Hotel AKA Back Bay
4.5-star property

Hotel AKA Back Bay

9.4/10 Exceptional! (1,338 reviews)

Oct 15 - Oct 19

4 night stay

Los Angeles (LAX) to Boston (BOS)

Frontier Airlines • Non-stop • FirstClass

Boston (BOS) to Los Angeles (LAX)

Delta • Non-stop • FirstClass
Price was $4,770, price is now $3,991 per person
$3,991
per person
found 1 day ago

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Brookline

If you are looking for affordable flights to Brookline, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Brookline now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Brookline flights. With Orbitz, booking flights to Brookline is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Brookline flights by visiting the Orbitz site or mobile application.

Orbitz looks after you

Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Brookline flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

After booking your Brookline flights, you may access your account profile on the Orbitz site and update your frequent flyer or loyalty membership details. This information will remain on the system and will be available for you to access when you make any future bookings with Orbitz.

Frequently asked questions

Which airlines fly to Brookline?
With 20 airlines running services to Logan Intl. Airport (BOS), a major entrance point to Brookline, you have plenty of choice. Find a fabulous deal among these renowned international airlines that'll take you to this city:

  • JetBlue - 175 flights to Brookline per month
  • Delta - 158 flights to Brookline per month
  • Air Canada - 151 flights to Brookline per month

What is the best airport to fly to in Brookline?
Keep your eyes peeled for a rewarding flight deal to Logan Intl. Airport (BOS). It's the city's main airport and is situated roughly 6 miles northeast of the downtown area. Once you've touched down, it won't be long before you're soaking up the very best of Brookline.
How much is a flight to Brookline?
If you're searching for return flights, airfares fluctuated from $110 to $128 this last week. The most affordable price for one-way was $57, originating in Orlando (MCO).
How to book the cheapest flight to Brookline?
Scoring cheap flights to Brookline is as easy as booking your ticket with Orbitz. But if you're eager to make sure you're nabbing the best flight deals around, here are a few tips to follow:

  • Depending on where you're departing from, select the 'Nearby airports' function (located under the departure and arrival options). In some cases, alternative departure points will have more competitive fares.
  • If your travel plans aren't written in stone, click on the 'Show flexible dates' link to browse flight deals for a range of departure dates. Go with any suitable cheaper fare that pops up.
  • You can also hit the 'Show options' link to filter results for your preferred carrier, seating class, and nonstop and refundable flights. Under 'Sort & Filter' to the left, you can even pick the time of day you want to fly.
  • The early bird catches the most rewarding savings, so book as soon as you've worked out your travel dates. The cheapest airfares sell like hotcakes and prices normally increase as the departure date nears.
  • Make even more savings on your vacation by combining your flights, hotels and car rental into an Orbitz package. Your bank account will thank you for it.
  • Flying during busier seasons can mean steep airfares. Try to plan your trip outside of popular periods, such as school breaks, Thanksgiving and Easter.

How long is a flight to Brookline?
The United States is big, so that depends on the city you're departing from. To make things simple, we've selected three of the major routes to Brookline and worked out their average flight times:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Logan Intl. Airport (BOS) - 1 hour and 44 minutes
  • New York, NY (LGA-LaGuardia) to Logan Intl. Airport (BOS) - 1 hour and 34 minutes
  • New York, NY (JFK-John F. Kennedy Intl.) to Logan Intl. Airport (BOS) - 1 hour and 17 minutes

What is the best time to book a flight to Brookline?
Book your tickets to Brookline in January. This is a fantastic month for bargain prices, followed by February and August. Find cheap flights and make your dream vacation a reality with Orbitz.
What day of the week is the cheapest to book a flight to Brookline?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days to book flights to Brookline. If you want the most competitive airfares, search across those days and you just might find an excellent flight deal.
What is the cheapest day of the week to fly to Brookline?
According to Orbitz data from 2020, you should start your vacation on a Monday to score cheap flights to Brookline. Next most affordable day? Tuesday. Saturday will cost the most. So, think about leaving early in the week if you'd like to book a bargain fare without paying premium prices.
What is the cheapest month to fly to Brookline?
To book cheap flights to Brookline, you should depart in August. If getting a great deal on your plane ticket is your main concern, Orbitz data has found that this is generally an excellent month to travel. June is when fares are the most expensive.
Which airlines allow free cancellation?
Things change, and your ticket should be able to as well. That's why Orbitz makes it a breeze to search for fares with no change fees and free cancellation. Just enter your travel details and then click on "Filter by flexible change policies." Talk about peace of mind!
What do I need for the flight to Brookline?
Flying doesn't have to be a drag. In fact it can be fun with a little pre-planning! Make your flight a stress-free one with these useful hints:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to step foot on the plane. You'll also need some kind of government-issued photo ID. If you're flying internationally, make sure your passport is valid and you've checked visa requirements.
  • Take some activities to keep you amused on your journey to Brookline. Books and devices like tablets and e-readers are ideal. Be sure to take a bottle of water with you too. Even on a short flight, it's important to keep hydrated.
  • Even if you're flying when it's 100 degrees outside, carry a hoodie or sweater on board with you. Cabins are notorious for getting a bit chilly!

How many direct flights are there to Brookline?
At present, there are 1,287 direct flights every month to Brookline. When it comes to airlines that will take you there, you have loads of options. JetBlue Airways, Delta Air Lines and American Airlines are some of the most popular. Cape Air, United Airlines and Southwest Airlines are other respected carriers that provide nonstop services.
How do I get cheap first-class/business deals to Brookline?
Smart travelers know how to find business or first-class airfares to Brookline that don't cost an arm and a leg. Follow in their footsteps with these useful hints:

  • Being flexible isn't confined to yoga. Leave some room to move around your travel dates so you can snap up more affordable airfares when a sale comes along.
  • Plenty of budget carriers nowadays have quality business or premium-class seating for a reasonable price.
  • Bid for an upgrade in online auctions (if available) or upgrade your fare through your loyalty program.

How to get into Brookline from the airport?
Hop off the plane at Logan Intl. Airport (BOS) and then collect the keys from one of the Logan Intl. Airport (BOS) car rental providers on-site, Enterprise or Advantage Rent-A-Car. With your own set of wheels, getting to the heart of Brookline from BOS will be a cinch. Set your GPS and head 6 miles to the west. Alternatively, you could use public transportation or take a taxi into town and rent a car directly from the city center. Take a look at the deals available on our Brookline car rentals.
What is the best time to go to Brookline?
Anytime is a fantastic time to vacation in Brookline, but July, August and October are the most popular months. Like most places in the Northern Hemisphere, the summer begins June 20. If you'd like to spend most of your days in a lightweight top than a winter jacket, this time of the year would suit you perfectly. Expect average daily highs of 80 ºF and nighttime lows around 65 ºF.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.