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Massachusetts

$134+ 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 1/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This Southwest deal was found by Cheapflights users on 12/17. 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.
Sat 12/275:15 amOAK - BOS
1 stop11h 15mSouthwest
Tue 1/66:50 amBOS - OAK
1 stop11h 05mSouthwest
Deal found 12/17$462
This Southwest deal was found by Cheapflights users on 12/16. 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.
Wed 12/2411:00 amOAK - BOS
1 stop7h 35mSouthwest
Thu 12/256:45 amBOS - OAK
2 stops10h 45mSouthwest
Deal found 12/16$612
This Southwest deal was found by Cheapflights users on 12/15. 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.
Fri 12/195:35 amOAK - BOS
1 stop9h 50mSouthwest
Sun 12/214:40 pmBOS - OAK
1 stop10h 40mSouthwest
Deal found 12/15$617
This Southwest deal was found by Cheapflights users on 12/17. 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.
Wed 12/1711:00 amOAK - BOS
1 stop7h 35mSouthwest
Wed 12/245:00 pmBOS - OAK
1 stop8h 20mSouthwest
Deal found 12/17$618
This Southwest deal was found by Cheapflights users on 12/16. 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.
Sat 12/275:15 amOAK - BOS
1 stop11h 15mSouthwest
Wed 12/311:35 pmBOS - OAK
2 stops11h 10mSouthwest
Deal found 12/16$619
This Southwest deal was found by Cheapflights users on 12/15. 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.
Thu 12/185:25 amOAK - ALB
1 stop7h 50mSouthwest
Tue 12/237:20 pmALB - OAK
1 stop8h 05mSouthwest
Deal found 12/15$842
This Southwest deal was found by Cheapflights users on 12/15. 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.
Wed 12/247:00 amOAK - ALB
1 stop7h 35mSouthwest
Mon 12/297:20 pmALB - OAK
1 stop8h 05mSouthwest
Deal found 12/15$857
This Southwest deal was found by Cheapflights users on 12/16. 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.
Sat 12/2012:45 pmOAK - ALB
1 stop10h 05mSouthwest
Sat 12/276:45 amALB - OAK
1 stop12h 20mSouthwest
Deal found 12/16$970
This Delta deal was found by Cheapflights users on 12/16. 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.
Thu 12/255:53 amOAK - ALB
2 stops13h 20mDelta
Wed 12/316:07 amALB - OAK
2 stops32h 47mDelta
Deal found 12/16$982
This Delta deal was found by Cheapflights users on 12/17. 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.
Mon 12/225:53 amOAK - BDL
2 stops12h 55mDelta
Mon 12/292:09 pmBDL - OAK
2 stops12h 49mDelta
Deal found 12/17$1,321
This Delta deal was found by Cheapflights users on 12/16. 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.
Sun 12/214:50 pmOAK - BDL
2 stops14h 25mDelta
Sat 12/2712:48 pmBDL - OAK
2 stops11h 57mDelta
Deal found 12/16$1,932

Find flight deals from Oakland to Massachusetts

Keep the following information in mind while searching for Oakland to Massachusetts flight deals. Data was last updated December 18, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$287
(Alaska Airlines)

One-way from

$134
(Southwest)

Popular in

December

Cheapest in

January

Average price

$474
Provider with most accurate pricing for San Francisco-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for San Francisco-Boston Logan Intl flights.
Search Deals
From Oakland to Massachusetts
Search Deals
One-way flight from Oakland to Massachusetts
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 18, 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

Thu 1/8

9:40 am-10:30 pm

1 stop9h 50m

Boston Logan Intl

Tue 1/13

5:30 am-2:05 pm

1 stop11h 35m

$287

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 1/21

5:55 am-4:30 pm

1 stop7h 35m

Boston Logan Intl

Mon 2/2

5:35 pm-11:53 pm

1 stop9h 18m

$297

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 1/23

4:54 pm-6:05 am

1 stop10h 11m

Boston Logan Intl

Tue 2/3

4:25 pm-11:53 pm

1 stop10h 28m

$297

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 1/23

4:54 pm-6:05 am

1 stop10h 11m

Boston Logan Intl

Mon 2/2

1:50 pm-11:53 pm

2 stops13h 03m

$302

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 1/9

4:54 pm-6:05 am

1 stop10h 11m

Boston Logan Intl

Mon 1/12

1:40 pm-10:53 pm

2 stops12h 13m

$302

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Sat 1/17

5:55 am-8:55 pm

1 stop12h 00m

Boston Logan Intl

Sat 1/24

6:05 am-4:40 pm

1 stop13h 35m

$304

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 1/23

11:43 am-11:54 pm

1 stop9h 11m

Boston Logan Intl

Tue 2/3

7:00 am-4:23 pm

1 stop12h 23m

$312

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 3/30

7:30 pm-8:05 am

2 stops9h 35m

Boston Logan Intl

Wed 4/1

7:15 am-12:45 pm

1 stop8h 30m

$320

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 1/21

12:33 pm-11:56 pm

1 stop8h 23m

Boston Logan Intl

Sat 1/31

6:10 am-11:52 am

1 stop8h 42m

$326

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Thu 1/22

11:43 am-11:54 pm

1 stop9h 11m

Boston Logan Intl

Mon 2/2

7:00 am-9:46 am

2 stops29h 46m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 50 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, December is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $118). Flying from Oakland, California to Massachusetts in June is currently the most expensive (average of $219). 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 December 18, 2025.

It’s optimal to fly from Oakland, California to Massachusetts at noon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the afternoon.

What is the cheapest day to fly from Oakland, California to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Oakland to Massachusetts. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Oakland, California to Massachusetts flight should consider departing on Friday evenings when fares are most often at their lowest. Thursday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 December 18, 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
11,477 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Alaska Airlines
8.0
Very good
11,477 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Southwest
7.9
Good
4,250 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
Delta
7.9
Good
8,005 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.
JetBlue
7.2
Good
2,897 reviews
Alaska Airlines
8.0
Very good
11,477 reviews

Comfort

7.8

Entertainment

7.0

Overall

8.0

Food

7.1

Crew

8.5

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Art,Dec 2025

SAN - OGG

It was a five hour flight and my seat did not recline. I have had three back surgeries and I’m solid bone for my L3 vertebrae all the way to my tailbone. My body has never hurt so much. There was no TV on this flight and only a small can of soda was free.

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 $297. 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?

    $98 is the cheapest one-way deal found within the past few days, from JetBlue. You may also be able to find cheap deals on Delta and Alaska Airlines, with prices starting from $118 and $144, 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 - Albany Intl and Oakland - Hartford Bradley 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, December is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $118). Flying from Oakland, California to Massachusetts in June is currently the most expensive (average of $219). 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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Top 4 airlines flying from Oakland to Massachusetts

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$149Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$208Average$386FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$289Average$458FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$326Average$466FlexibilityNo cancel feeOn-time63%

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