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$126+ Cheap flights from Oakland, CA (OAK) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap flight deals from Oakland to Massachusetts

Keep the following information in mind while searching for Oakland to Massachusetts flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$288
(Southwest)

One-way from

$126
(Southwest)

Popular in

December

Cheapest in

January

Average price

$348
From Oakland to Massachusetts
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One-way flight from Oakland to Massachusetts
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Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Oakland to Massachusetts

Cheapest flights from Oakland to Massachusetts
Explore the most affordable flight options available from Oakland to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/195:45 amOAK - BOS
1 stop7h 20mSouthwest
lun. 11/246:20 pmBOS - OAK
1 stop8h 50mSouthwest
Deal found 9/16$288
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:50 amOAK - BOS
1 stop9h 25mSouthwest
mar. 12/166:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 9/14$293
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/24:54 pmOAK - BOS
1 stop10h 36mDelta
mar. 12/96:47 pmBOS - OAK
1 stop8h 21mDelta
Deal found 9/14$297
This Delta deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/2512:30 pmOAK - BOS
1 stop8h 18mDelta
mar. 10/286:50 pmBOS - OAK
1 stop8h 03mDelta
Deal found 9/16$298
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/612:30 pmOAK - BOS
1 stop8h 10mDelta
lun. 12/156:47 pmBOS - OAK
1 stop8h 21mDelta
Deal found 9/14$299
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/225:50 amOAK - BDL
1 stop7h 25mSouthwest
mar. 10/284:15 pmBDL - OAK
2 stops9h 45mSouthwest
Deal found 9/16$306
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/251:10 pmOAK - BOS
1 stop7h 10mSouthwest
mié. 10/295:00 amBOS - OAK
2 stops10h 00mSouthwest
Deal found 9/15$307
This Alaska Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/296:30 amOAK - BOS
1 stop14h 50mAlaska Airlines
mar. 11/47:00 amBOS - OAK
1 stop9h 55mAlaska Airlines
Deal found 9/15$310
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/126:50 amOAK - BOS
1 stop9h 25mSouthwest
mié. 12/176:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 9/14$311
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/2710:10 amOAK - ALB
2 stops10h 35mSouthwest
vie. 10/312:25 pmALB - OAK
2 stops9h 45mSouthwest
Deal found 9/14$338
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/218:45 amOAK - ALB
2 stops9h 10mSouthwest
vie. 10/245:10 pmALB - OAK
1 stop8h 45mSouthwest
Deal found 9/16$353
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/2412:20 pmOAK - ALB
2 stops8h 00mSouthwest
vie. 10/312:25 pmALB - OAK
2 stops9h 45mSouthwest
Deal found 9/16$377

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Oakland to Massachusetts that are best for you.

Fly from

Oakland

Fly to

Massachusetts

Route

Depart

Return

Price

OaklandBoston

OAK - BOS

OAKBOS

Oakland

lun. 2/2

6:15 am-4:50 pm

1 stop7h 35m

Boston Logan Intl

mié. 2/11

6:50 am-2:55 pm

1 stop11h 05m

$298

OaklandBoston

OAK - BOS

OAKBOS

Oakland

mar. 3/3

6:35 pm-7:16 am

1 stop9h 41m

Boston Logan Intl

mié. 3/4

10:00 am-5:43 pm

1 stop10h 43m

$300

OaklandHartford

OAK - BDL

OAKBDL

Oakland

mié. 10/22

5:50 am-4:15 pm

1 stop7h 25m

Hartford Bradley Intl

mar. 10/28

4:15 pm-11:00 pm

2 stops9h 45m

$306

OaklandBoston

OAK - BOS

OAKBOS

Oakland

jue. 11/13

6:30 am-12:20 am

1 stop14h 50m

Boston Logan Intl

sáb. 11/15

7:00 am-1:55 pm

1 stop9h 55m

$320

OaklandBoston

OAK - BOS

OAKBOS

Oakland

sáb. 10/18

1:10 pm-11:20 pm

1 stop7h 10m

Boston Logan Intl

mié. 10/22

5:00 am-12:00 pm

2 stops10h 00m

$342

OaklandBoston

OAK - BOS

OAKBOS

Oakland

sáb. 11/1

9:30 am-12:20 am

2 stops11h 50m

Boston Logan Intl

mar. 11/4

7:00 am-1:55 pm

1 stop9h 55m

$345

OaklandBoston

OAK - BOS

OAKBOS

Oakland

mar. 10/14

5:20 am-4:55 pm

1 stop8h 35m

Boston Logan Intl

mar. 11/4

6:45 am-1:55 pm

2 stops10h 10m

$352

OaklandHartford

OAK - BDL

OAKBDL

Oakland

mié. 11/19

9:00 am-10:05 pm

2 stops10h 05m

Hartford Bradley Intl

mié. 12/3

5:15 am-1:00 pm

2 stops10h 45m

$354

OaklandBoston

OAK - BOS

OAKBOS

Oakland

mié. 11/12

9:48 am-12:20 am

2 stops11h 32m

Boston Logan Intl

sáb. 11/15

7:00 am-1:55 pm

1 stop9h 55m

$359

OaklandBoston

OAK - BOS

OAKBOS

Oakland

sáb. 10/18

6:40 am-7:25 pm

1 stop9h 45m

Boston Logan Intl

mié. 10/22

7:20 am-12:03 am

1 stop19h 43m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 48 results
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Best time to book a flight from Oakland to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Massachusetts

What is the cheapest month to book a flight from Oakland, California to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $218). Flying from Oakland, California to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from OAK to MA?

Find hourly flight availability from Oakland to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Oakland, California to Massachusetts as you normally would.

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated septiembre 16, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta from Oakland to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Southwest
8.0
Very good
4,242 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,957 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
United Airlines
7.4
Good
8,924 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
JetBlue
7.2
Good
2,914 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Oakland to Massachusetts?

    Located just 7.0 mi from the city center, Oakland (OAK) is the airport most travelers will use when flying to Massachusetts from Oakland.

  • How long is the flight from Oakland, California to Massachusetts?

    A quick flight from Oakland, California to Massachusetts can take about 7h 35m. Southwest provides one of the quickest options available for as low as $298. The distance from Oakland, California to Massachusetts is about 2685 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Oakland, California to Massachusetts one-way?

    $126 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Spirit Airlines and Alaska Airlines, with prices starting from $129 and $139, respectively.

  • What are the most popular routes from Oakland, California to Massachusetts?

    The most popular flight routes from Oakland, California to Massachusetts are Oakland - Boston Logan Intl, Oakland - Hartford Bradley Intl and Oakland - Albany Intl.

  • Can I find deals for flights from Oakland to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Oakland to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Massachusetts.

  • Can I find deals for business class flights from Oakland to Massachusetts?

    Yes. Cheapflights offers flight deals from Oakland to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $218). Flying from Oakland, California to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Oakland to Massachusetts

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Top 5 airlines flying from Oakland to Massachusetts

Discover the top 5 airlines that operate flights from Oakland to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$148Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$222Average$419FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$329FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$289Average$465FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$324Average$487FlexibilityNo cancel feeOn-time63%

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