Massachusetts

$146+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — BOS
Apr 19 — Apr 261
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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 March 20, 2026.

This Southwest deal was found by Cheapflights users on 3/18. 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 5/67:35 pm
OAK
-
BDL
2 stops9h 35m
Southwest
Tue 5/126:20 pm
BDL
-
OAK
1 stop8h 05m
Southwest
Deal found 3/18$296
This Southwest deal was found by Cheapflights users on 3/17. 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 4/2211:55 pm
OAK
-
BDL
1 stop7h 45m
Southwest
Mon 4/277:20 pm
BDL
-
OAK
1 stop8h 05m
Southwest
Deal found 3/17$301
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/97:03 pm
OAK
-
BOS
1 stop8h 17m
Alaska Airlines
Tue 6/167:36 pm
BOS
-
OAK
1 stop16h 50m
Alaska Airlines
Deal found 3/17$307
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 6/211:55 pm
OAK
-
BDL
1 stop7h 45m
Southwest
Wed 6/36:20 pm
BDL
-
OAK
1 stop8h 05m
Southwest
Deal found 3/15$311
This CheapOair deal was found by Cheapflights users on 3/19. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/21:01 pm
OAK
-
BOS
1 stop15h 40m
Alaska Airlines
Tue 6/167:36 pm
BOS
-
OAK
1 stop16h 50m
Alaska Airlines
Deal found 3/19$312
This CheapOair deal was found by Cheapflights users on 3/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:20 am
OAK
-
BOS
1 stop14h 39m
Alaska Airlines
Wed 5/69:00 am
BOS
-
OAK
1 stop16h 32m
Alaska Airlines
Deal found 3/17$317
This Delta deal was found by Cheapflights users on 3/18. 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 4/1512:34 pm
OAK
-
BOS
1 stop8h 23m
Delta
Wed 4/222:48 pm
BOS
-
OAK
2 stops12h 06m
Delta
Deal found 3/18$322
This Southwest deal was found by Cheapflights users on 3/16. 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.
Tue 4/285:50 am
OAK
-
BDL
1 stop7h 10m
Southwest
Fri 5/17:20 pm
BDL
-
OAK
1 stop8h 05m
Southwest
Deal found 3/16$326
This Southwest deal was found by Cheapflights users on 3/17. 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 4/295:50 am
OAK
-
BOS
1 stop7h 15m
Southwest
Wed 5/134:45 pm
BOS
-
OAK
1 stop8h 20m
Southwest
Deal found 3/17$327
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 3/3111:55 pm
OAK
-
BOS
1 stop8h 25m
Southwest
Tue 4/76:20 pm
BOS
-
OAK
1 stop8h 05m
Southwest
Deal found 3/15$332
This Delta deal was found by Cheapflights users on 3/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:04 pm
OAK
-
BDL
2 stops14h 39m
Delta
Wed 5/63:00 pm
BDL
-
OAK
2 stops11h 54m
Delta
Deal found 3/15$334
This Southwest deal was found by Cheapflights users on 3/15. 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 4/2911:55 pm
OAK
-
BDL
1 stop7h 45m
Southwest
Thu 4/307:20 pm
BDL
-
OAK
1 stop8h 05m
Southwest
Deal found 3/15$336

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 March 20, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$296
(Southwest)

One-way from

$146
(Southwest)

Popular in

December

Cheapest in

January

Average price

$412
Provider with most accurate pricing for San Francisco-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for San Francisco-Boston Logan Intl flights.
From Oakland to Massachusetts
One-way flight from Oakland to Massachusetts
High demand for flights, 0% potential price rise
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 20, 2026.
Use the filters below to find and compare flights from Oakland to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Wed 4/22

11:55 pm-10:40 am

1 stop7h 45m

Hartford Bradley Intl

Mon 4/27

7:20 pm-12:25 am

1 stop8h 05m

$301
Quickest round-trip

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Tue 4/28

5:50 am-4:00 pm

1 stop7h 10m

Hartford Bradley Intl

Fri 5/1

7:20 pm-12:25 am

1 stop8h 05m

$326

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 3/31

5:55 am-8:14 pm

2 stops11h 19m

Boston Logan Intl

Tue 4/7

2:50 pm-11:46 pm

2 stops11h 56m

$362

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Sun 5/10

11:55 pm-10:40 am

1 stop7h 45m

Hartford Bradley Intl

Wed 5/13

6:20 pm-11:25 pm

1 stop8h 05m

$376

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Wed 4/22

6:10 am-6:35 pm

2 stops9h 25m

Boston Logan Intl

Wed 5/6

11:40 am-6:50 pm

2 stops10h 10m

$378

OaklandAlbany

OAK - ALB

OAKALB

Oakland

Thu 4/16

7:30 pm-8:00 am

2 stops9h 30m

Albany Intl

Thu 4/23

7:25 pm-12:25 am

1 stop8h 00m

$379

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Fri 5/29

12:50 pm-12:50 am

2 stops9h 00m

Boston Logan Intl

Fri 6/12

4:45 pm-12:10 am

1 stop10h 25m

$382

OaklandHartford

OAK - BDL

OAKBDL

Oakland

Fri 7/31

11:55 pm-10:55 am

1 stop8h 00m

Hartford Bradley Intl

Sat 8/8

11:45 am-7:10 pm

2 stops10h 25m

$396

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Thu 5/7

2:50 pm-12:50 am

1 stop7h 00m

Boston Logan Intl

Sat 5/9

5:15 am-12:25 pm

2 stops10h 10m

$402

OaklandBoston

OAK - BOS

OAKBOS

Oakland

Tue 5/12

1:30 pm-12:05 am

1 stop7h 35m

Boston Logan Intl

Fri 5/22

3:45 pm-10:45 pm

2 stops10h 00m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 55 resultsSorted by cheapest first
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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 January is currently the most expensive (average of $189). 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.

How much does it cost to fly round-trip from Oakland, California to Massachusetts?

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 20, 2026.
Read reviews from past customers who have flown Southwest,Alaska Airlines, andDelta from Oakland to Massachusetts. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Food

7.0

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 45m. Southwest provides one of the quickest options available for as low as $301. The distance from Oakland, California to Massachusetts is about 2606 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?

    $113 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?

  • 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 January is currently the most expensive (average of $189). 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.

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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$149Average$293FlexibilityNo cancel feeOn-time62%
DeltaCheapest$208Average$363FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$287Average$433FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$307Average$486FlexibilityNo cancel feeOn-time63%

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