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$129+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$239
(Booking.com)

One-way from

$129
(Hawaiian Airlines)

Popular in

December

Cheapest in

January

Average price

$433
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. 1% potential increase in price ($5 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 31, 2025.

This Booking.com deal was found by Cheapflights users on 7/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/166:00 amOAK - BOS
2 stops10h 00mSpirit Airlines
Mon 10/204:59 pmBOS - OAK
2 stops17h 39mSpirit Airlines
Deal found 7/31$239
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/276:00 amOAK - BDL
2 stops14h 23mSpirit Airlines
Wed 9/36:45 amBDL - OAK
2 stops19h 42mSpirit Airlines
Deal found 7/30$246
This Alaska Airlines deal was found by Cheapflights users on 7/31. 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.
Mon 9/87:07 pmOAK - BOS
1 stop7h 53mAlaska Airlines
Sat 9/137:20 amBOS - OAK
1 stop9h 16mAlaska Airlines
Deal found 7/31$268
This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 12/126:50 amOAK - BOS
1 stop9h 25mSouthwest
Wed 12/176:45 amBOS - OAK
2 stops10h 10mSouthwest
Deal found 7/30$273
This Southwest deal was found by Cheapflights users on 7/31. 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 11/65:35 amOAK - ALB
1 stop9h 25mSouthwest
Mon 11/106:45 pmALB - OAK
1 stop8h 20mSouthwest
Deal found 7/31$277
This Delta deal was found by Cheapflights users on 7/29. 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.
Wed 9/312:35 pmOAK - BOS
1 stop8h 23mDelta
Wed 9/105:20 pmBOS - OAK
1 stop8h 26mDelta
Deal found 7/29$297
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 8/275:35 amOAK - BDL
1 stop12h 55mSouthwest
Wed 9/36:25 amBDL - OAK
1 stop14h 15mSouthwest
Deal found 7/30$305
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/216:00 amOAK - BOS
2 stops13h 34mMultiple Airlines
Mon 8/2510:39 amBOS - OAK
2 stops15h 48mMultiple Airlines
Deal found 7/31$311
This Delta deal was found by Cheapflights users on 7/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/136:00 amOAK - BDL
2 stops11h 28mDelta
Sat 8/236:00 amBDL - OAK
2 stops13h 16mDelta
Deal found 7/30$417
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:30 amOAK - BDL
3 stops25h 05mMultiple Airlines
Sun 10/56:00 amBDL - OAK
1 stop10h 34mMultiple Airlines
Deal found 7/30$451
This Mytrip deal was found by Cheapflights users on 7/31. 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 9/186:30 amOAK - ALB
2 stops24h 40mMultiple Airlines
Sun 9/211:20 pmALB - OAK
3 stops27h 14mMultiple Airlines
Deal found 7/31$524
This Delta deal was found by Cheapflights users on 7/31. 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.
Sat 8/164:58 pmOAK - ALB
2 stops15h 16mDelta
Wed 8/205:02 pmALB - OAK
2 stops9h 48mDelta
Deal found 7/31$669

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 July 31, 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 10/16

6:00 am-7:00 pm

2 stops10h 00m

Boston Logan Intl

Mon 10/20

4:59 pm-7:38 am

2 stops17h 39m

$239

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Wed 8/27

6:00 am-11:23 pm

2 stops14h 23m

Hartford Bradley Intl

Wed 9/3

6:45 am-11:27 pm

2 stops19h 42m

$246

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 9/8

7:07 pm-6:00 am

1 stop7h 53m

Boston Logan Intl

Sat 9/13

7:20 am-1:36 pm

1 stop9h 16m

$268

OaklandAlbany

OAK - ALB

OAKALB

Oakland

Thu 11/6

5:35 am-6:00 pm

1 stop9h 25m

Albany Intl

Mon 11/10

6:45 pm-12:05 am

1 stop8h 20m

$277

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Mon 9/8

5:15 am-3:20 pm

1 stop7h 05m

Boston Logan Intl

Thu 9/11

1:45 pm-9:05 pm

1 stop10h 20m

$279

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 9/3

12:35 pm-11:58 pm

1 stop8h 23m

Boston Logan Intl

Wed 9/10

5:20 pm-10:46 pm

1 stop8h 26m

$297

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Wed 8/27

5:35 am-9:30 pm

1 stop12h 55m

Hartford Bradley Intl

Wed 9/3

6:25 am-5:40 pm

1 stop14h 15m

$305

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Thu 8/21

6:00 am-10:34 pm

2 stops13h 34m

Boston Logan Intl

Mon 8/25

10:39 am-11:27 pm

2 stops15h 48m

$311

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Wed 8/13

6:00 am-8:28 pm

2 stops11h 28m

Hartford Bradley Intl

Sat 8/23

6:00 am-4:16 pm

2 stops13h 16m

$417

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Thu 10/2

6:30 am-10:35 am

3 stops25h 05m

Hartford Bradley Intl

Sun 10/5

6:00 am-1:34 pm

1 stop10h 34m

$451

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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 July 31, 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

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Hawaiian Airlines
7.8
Good
2,611 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Sun Country Air
6.9
Okay
334 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Crew

8.5

Food

7.1

Overall

8.0

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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?

    $129 is the cheapest one-way deal found within the past few days, from Hawaiian Airlines. You may also be able to find cheap deals on Alaska Airlines and Spirit Airlines, with prices starting from $134 and $135, 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$148Average$288FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$182Average$252FlexibilityNo cancel feeOn-time65%
DeltaCheapest$227Average$431FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$329FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$289Average$473FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$324Average$482FlexibilityNo cancel feeOn-time63%

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