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$111+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$237
(Mytrip)

One-way from

$111
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$356
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. 12% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/207:46 amOAK - BOS
2 stops26h 28mSpirit Airlines
Tue 4/2912:29 pmBOS - OAK
2 stops32h 05mSpirit Airlines
Deal found 3/27$237
This Southwest deal was found by Cheapflights users on 3/26. 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 4/27:30 pmOAK - BOS
2 stops9h 50mSouthwest
Mon 4/74:00 pmBOS - OAK
1 stop11h 30mSouthwest
Deal found 3/26$277
This Alaska Airlines deal was found by Cheapflights users on 3/27. 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 5/24:43 pmOAK - BOS
1 stop12h 12mAlaska Airlines
Mon 5/56:35 pmBOS - OAK
1 stop17h 00mAlaska Airlines
Deal found 3/27$289
This Delta deal was found by Cheapflights users on 3/27. 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.
Wed 5/144:55 pmOAK - BOS
1 stop10h 25mDelta
Thu 5/296:47 pmBOS - OAK
1 stop8h 02mDelta
Deal found 3/27$297
This Expedia deal was found by Cheapflights users on 3/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/288:37 pmOAK - BOS
2 stops14h 42mMultiple Airlines
Sat 5/35:20 pmBOS - OAK
1 stop9h 24mMultiple Airlines
Deal found 3/27$314
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:46 amOAK - BDL
3 stops22h 41mSpirit Airlines
Thu 5/112:55 pmBDL - OAK
2 stops20h 54mSpirit Airlines
Deal found 3/27$328
This Sun Country Air deal was found by Cheapflights users on 3/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/245:50 pmOAK - BDL
1 stop13h 57mSun Country Air
Thu 7/3111:42 amBDL - OAK
1 stop8h 09mSun Country Air
Deal found 3/26$335
This Southwest deal was found by Cheapflights users on 3/26. 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 7/2410:15 amOAK - BDL
2 stops10h 35mSouthwest
Thu 7/315:15 amBDL - OAK
1 stop9h 30mSouthwest
Deal found 3/26$404
This Trip.com deal was found by Cheapflights users on 3/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/116:00 amOAK - BOS
1 stop15h 12mHawaiian Airlines
Sun 5/186:00 amBOS - OAK
1 stop29h 45mHawaiian Airlines
Deal found 3/27$434
This Southwest deal was found by Cheapflights users on 3/28. 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 7/297:05 pmOAK - ALB
2 stops9h 50mSouthwest
Tue 8/512:30 pmALB - OAK
2 stops10h 10mSouthwest
Deal found 3/28$438
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/247:46 amOAK - BDL
1 stop12h 40mMultiple Airlines
Thu 5/112:55 pmBDL - OAK
2 stops20h 54mMultiple Airlines
Deal found 3/27$441
This Delta deal was found by Cheapflights users on 3/26. 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 5/512:55 pmOAK - ALB
2 stops24h 23mDelta
Wed 5/76:55 pmALB - OAK
2 stops31h 54mDelta
Deal found 3/26$480

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 March 28, 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

Sun 4/20

7:46 am-1:14 pm

2 stops26h 28m

Boston Logan Intl

Tue 4/29

12:29 pm-5:34 pm

2 stops32h 05m

$237

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 5/2

4:43 pm-7:55 am

1 stop12h 12m

Boston Logan Intl

Mon 5/5

6:35 pm-8:35 am

1 stop17h 00m

$289

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 5/14

4:55 pm-6:20 am

1 stop10h 25m

Boston Logan Intl

Thu 5/29

6:47 pm-11:49 pm

1 stop8h 02m

$297

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 4/28

8:37 pm-2:19 pm

2 stops14h 42m

Boston Logan Intl

Sat 5/3

5:20 pm-11:44 pm

1 stop9h 24m

$314

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Thu 4/24

7:46 am-9:27 am

3 stops22h 41m

Hartford Bradley Intl

Thu 5/1

12:55 pm-6:49 am

2 stops20h 54m

$328

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Thu 7/24

5:50 pm-10:47 am

1 stop13h 57m

Hartford Bradley Intl

Thu 7/31

11:42 am-4:51 pm

1 stop8h 09m

$335

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 4/7

7:35 pm-8:10 am

2 stops9h 35m

Boston Logan Intl

Thu 4/10

3:30 pm-11:20 pm

1 stop10h 50m

$343

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Thu 7/24

10:15 am-11:50 pm

2 stops10h 35m

Hartford Bradley Intl

Thu 7/31

5:15 am-11:45 am

1 stop9h 30m

$404

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Sun 5/11

6:00 am-12:12 am

1 stop15h 12m

Boston Logan Intl

Sun 5/18

6:00 am-8:45 am

1 stop29h 45m

$434

OaklandAlbany

OAK - ALB

OAKALB

Oakland

Tue 7/29

7:05 pm-7:55 am

2 stops9h 50m

Albany Intl

Tue 8/5

12:30 pm-7:40 pm

2 stops10h 10m

$438

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Showing 1-10 of 29 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 March 28, 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.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 March 28, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines and Delta from Oakland to Massachusetts to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Hawaiian Airlines
7.9
Good
2,335 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Sun Country Air
6.9
Okay
348 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

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

    $111 is the cheapest one-way deal found within the past few days, from Spirit Airlines. You may also be able to find cheap deals on Southwest and Hawaiian Airlines, with prices starting from $114 and $145, 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.

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 6 airlines flying from Oakland to Massachusetts

Discover the top 6 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$145Average$295FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$182Average$277FlexibilityNo cancel feeOn-time65%
DeltaCheapest$224Average$472FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$329FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$306Average$488FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$311Average$491FlexibilityNo cancel feeOn-time75%
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