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$109+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$245
(Alaska Airlines)

One-way from

$109
(Southwest)

Popular in

June

Cheapest in

January

Average price

$395
Provider with most accurate pricing for San Francisco-Boston Logan Intl flight deals.
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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. 9% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Southwest deal was found by Cheapflights users on 10/28. 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.
Tue 12/912:35 pmOAK - BOS
1 stop7h 10mSouthwest
Wed 12/106:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 10/28$222
This Alaska Airlines deal was found by Cheapflights users on 10/28. 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.
Sat 12/139:45 amOAK - BOS
1 stop26h 39mAlaska Airlines
Thu 1/85:20 pmBOS - OAK
1 stop19h 26mAlaska Airlines
Deal found 10/28$251
This Southwest deal was found by Cheapflights users on 10/28. 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.
Mon 11/1712:35 pmOAK - BOS
1 stop7h 10mSouthwest
Tue 11/186:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 10/28$252
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Fri 12/57:59 pmOAK - BOS
1 stop16h 25mAlaska Airlines
Mon 12/86:59 pmBOS - OAK
1 stop18h 42mAlaska Airlines
Deal found 10/29$257
This Alaska Airlines deal was found by Cheapflights users on 10/30. 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.
Sat 11/156:30 amOAK - BOS
1 stop14h 50mAlaska Airlines
Mon 12/86:59 pmBOS - OAK
1 stop18h 42mAlaska Airlines
Deal found 10/30$267
This Alaska Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:30 amOAK - BOS
1 stop14h 50mAlaska Airlines
Tue 11/187:00 amBOS - OAK
1 stop9h 55mAlaska Airlines
Deal found 10/29$277
This Southwest deal was found by Cheapflights users on 10/30. 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.
Mon 12/812:35 pmOAK - BOS
1 stop7h 10mSouthwest
Thu 12/116:45 amBOS - OAK
1 stop10h 55mSouthwest
Deal found 10/30$282
This Southwest deal was found by Cheapflights users on 10/30. 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 11/155:10 amOAK - BOS
1 stop7h 40mSouthwest
Mon 12/86:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 10/30$297
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/512:30 pmOAK - BOS
1 stop8h 11mDelta
Mon 12/82:35 pmBOS - OAK
2 stops12h 33mDelta
Deal found 10/29$302
This Southwest deal was found by Cheapflights users on 10/29. 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 11/195:45 amOAK - BOS
1 stop7h 20mSouthwest
Sat 11/227:55 pmBOS - OAK
1 stop8h 35mSouthwest
Deal found 10/29$305
This Delta deal was found by Cheapflights users on 10/29. 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.
Fri 12/55:55 amOAK - BDL
2 stops12h 16mDelta
Mon 12/85:10 pmBDL - OAK
2 stops9h 58mDelta
Deal found 10/29$307
This Southwest deal was found by Cheapflights users on 10/28. 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 12/119:40 amOAK - BDL
2 stops9h 25mSouthwest
Mon 12/153:40 pmBDL - OAK
2 stops9h 40mSouthwest
Deal found 10/28$361

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 October 30, 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 11/13

6:30 am-12:20 am

1 stop14h 50m

Boston Logan Intl

Tue 11/18

7:00 am-1:55 pm

1 stop9h 55m

$277

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 12/8

12:35 pm-10:45 pm

1 stop7h 10m

Boston Logan Intl

Thu 12/11

6:45 am-2:40 pm

1 stop10h 55m

$282

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 11/19

5:45 am-4:05 pm

1 stop7h 20m

Boston Logan Intl

Sat 11/22

7:55 pm-1:30 am

1 stop8h 35m

$305

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Fri 12/5

5:55 am-9:11 pm

2 stops12h 16m

Hartford Bradley Intl

Mon 12/8

5:10 pm-12:08 am

2 stops9h 58m

$307

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 12/5

5:55 am-9:26 pm

2 stops12h 31m

Boston Logan Intl

Mon 12/8

5:40 am-4:04 pm

2 stops13h 24m

$307

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 11/18

12:28 pm-11:43 pm

1 stop8h 15m

Boston Logan Intl

Wed 12/10

6:10 am-11:50 am

1 stop8h 40m

$307

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 12/8

4:50 pm-10:10 am

2 stops14h 20m

Boston Logan Intl

Thu 12/11

2:35 pm-12:08 am

2 stops12h 33m

$307

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 11/18

5:55 am-4:10 pm

1 stop7h 15m

Boston Logan Intl

Tue 12/9

6:46 pm-12:08 am

1 stop8h 22m

$307

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 11/17

4:51 pm-6:30 am

1 stop10h 39m

Boston Logan Intl

Wed 12/10

6:46 pm-12:08 am

1 stop8h 22m

$307

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Thu 12/11

9:40 am-10:05 pm

2 stops9h 25m

Hartford Bradley Intl

Mon 12/15

3:40 pm-10:20 pm

2 stops9h 40m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 42 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, March is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $127). Flying from Oakland, California to Massachusetts in December is currently the most expensive (average of $185). 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 October 30, 2025.

It’s optimal to fly from Oakland, California to Massachusetts in the evening. By choosing this option you can save up to 35% 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 October 30, 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
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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
11,218 reviews
Alaska Airlines
8.0
Very good
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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
4,243 reviews
Alaska Airlines
8.0
Very good
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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
7.9
Good
7,998 reviews
Alaska Airlines
8.0
Very good
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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
8,995 reviews
Alaska Airlines
8.0
Very good
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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
2,906 reviews
Alaska Airlines
8.0
Very good
11,218 reviews

Overall

8.0

Boarding

8.1

Entertainment

7.0

Crew

8.5

Comfort

7.8

Food

7.1

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 10m. Alaska Airlines provides one of the quickest options available for as low as $282. 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?

    $119 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on Delta and Alaska Airlines, with prices starting from $149 and $153, 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, March is the cheapest month in which you can book a flight from Oakland, California to Massachusetts (average of $127). Flying from Oakland, California to Massachusetts in December is currently the most expensive (average of $185). 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.

See more FAQs

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Alternative routes for Oakland to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$164Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$237Average$384FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$289Average$465FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$317Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$326Average$472FlexibilityNo cancel feeOn-time63%

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