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Find cheap flights from Oakland to Massachusetts from $81

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oakland to Massachusetts departing on 8/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Wed 7/10
Wed 7/17

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Best Massachusetts Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Boston
Boston1 stop$162
West Tisbury
West Tisbury3 stops$980
Albany
Albany1 stop$462

Good to know

Low season

February

High season

June

Cheapest flight

$81
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Oakland to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from Oakland to Massachusetts?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Oakland to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oakland to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Massachusetts from Oakland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Oakland to Massachusetts?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Massachusetts with an airline and back to Oakland with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oakland to Massachusetts?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Massachusetts from Oakland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Massachusetts

  • Morning departure is around 27% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top airlines flying from Oakland to Massachusetts

Need help choosing which airline to fly with from Oakland to Massachusetts? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 10295 reviews
8.6Crew
7.9Comfort
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

2.0 MediocreE A, Jun 2024CLT - BOS
Read more about Delta reviews

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

There was a loud squeaky sound the whole time we were flying.

I didn’t not like that I could not select my seat and ended up with the worse seat.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

Terrible. Delta delays caused us to miss our flight and they did nothing to fix it.

Flight was canceled less than 6 hours before takeoff, rebooked on a flight that was twice as long and left earlier so we couldn’t make it, when using text support option took over 2 hours to speak with someone.

Terrible legroom, seats do not recline, tray table the size of an iPhone, delayed flight, have to pay 5$ to get a cup of water onboard.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

Worst airline experience ever. Lost my IPad going thru security. Charged for my dog carriage at the gate not at ticket counter. Gave away my seat 6D. Expressed I wanted my seat back after charging me 99 for dog carriage. Should have thrown it out. Had a 16 yr old Yorkie heading to Boston after being a snowbird. Seats small. Very bad experience. Still don’t have my IPad. Horrible

My mother was HARASSED AND ACCOSTED by the gate agent for her bag. I pre purchased the bag fee and the gate agent made my 78 year old mother board, deplane, re pay for her bag fee and board again. The gate agent made my mother pick up her own bag and REFUSED to help her, she is an older woman who wasn’t bothering anyone on a flight that had maybe 30’total passengers. I am going to sue this airlines for their HORRIBLE customer service and treatment of my mother, and all this occurred the day after Mother’s Day!!!

Horrible, first flight delayed. They switched my connecting flight while I was en route and even though I was originally supposed to be on the flight going back home to boston, refused to let me board and told me I would have to wait for next flight that was 14 hours later. Ended up renting a car and driving 6.5 hours back home. Still getting messages about flight and it is now showing that the other flight they put me on is now canceled and I would have to wait 24 hours for the next one. I will never book with spirit again

They stuck us with multiple extra fees. I will never fly spirit again

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

Book cheap flights from Oakland to Massachusetts

Recent round-trip flight deals

8/14Wed
1 stopSpirit Airlines
16h 05mOAK-BOS
8/21Wed
1 stopSpirit Airlines
9h 43mBOS-OAK
$162
8/14Wed
1 stopSpirit Airlines
16h 05mOAK-BOS
8/24Sat
1 stopSpirit Airlines
9h 43mBOS-OAK
$173
8/27Tue
1 stopSpirit Airlines
16h 05mOAK-BOS
9/10Tue
2 stopsSpirit Airlines
19h 26mBOS-OAK
$174
8/14Wed
1 stopSpirit Airlines
16h 05mOAK-BOS
8/20Tue
1 stopSpirit Airlines
9h 43mBOS-OAK
$176
8/6Tue
1 stop
9h 20mOAK-BOS
8/20Tue
1 stop
9h 43mBOS-OAK
$221
7/10Wed
2 stops
17h 27mOAK-BOS
7/18Thu
1 stop
12h 07mBOS-OAK
$255
11/7Thu
1 stopDelta
9h 38mOAK-BOS
11/12Tue
1 stopDelta
9h 17mBOS-OAK
$296
7/15Mon
1 stopSun Country Air
13h 41mOAK-BOS
7/18Thu
1 stopSun Country Air
12h 07mBOS-OAK
$299
7/11Thu
1 stopSun Country Air
14h 36mOAK-BDL
7/14Sun
1 stopSun Country Air
13h 24mBDL-OAK
$338
7/23Tue
1 stopDelta
8h 48mOAK-BDL
7/31Wed
1 stopDelta
10h 45mBDL-OAK
$456

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Recent one-way flight deals

8/14Wed
1 stopSpirit Airlines
16h 05mOAK-BOS
$81
8/14Wed
1 stopSpirit Airlines
16h 05mOAK-BOS
$82
7/29Mon
1 stopDelta
8h 00mOAK-BOS
$148
7/11Thu
1 stopSun Country Air
14h 36mOAK-BDL
$150
7/14Sun
1 stopSun Country Air
8h 01mOAK-BOS
$150
7/30Tue
1 stopDelta
8h 48mOAK-BDL
$163
6/26Wed
3 stops
34h 52mOAK-BDL
$166
6/27Thu
1 stop
7h 51mOAK-BDL
$185
7/17Wed
1 stopAlaska Airlines
9h 20mOAK-BOS
$215
9/5Thu
1 stopAlaska Airlines
19h 53mOAK-BOS
$235

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Last minute flights from Oakland to Massachusetts

Last minute flight, train and bus deals

6/12Wed
multi-stopSpirit Airlines
30h 34mOAK-BOS
6/19Wed
multi-stopSpirit Airlines
30h 12mBOS-OAK
$360
6/11Tue
multi-stopDelta
9h 16mOAK-BOS
7/11Thu
multi-stopDelta
8h 06mBOS-OAK
$509
6/12Wed
multi-stopSpirit Airlines
17h 59mOAK-BOS
6/19Wed
multi-stopSpirit Airlines
24h 20mBOS-OAK
$526
6/11Tue
multi-stopDelta
7h 53mOAK-BOS
6/19Wed
multi-stopDelta
8h 45mBOS-OAK
$534
6/15Sat
multi-stopSpirit Airlines
15h 44mOAK-BOS
6/20Thu
multi-stopSpirit Airlines
15h 24mBOS-OAK
$544
6/15Sat
multi-stopSpirit Airlines
15h 44mOAK-BOS
6/22Sat
multi-stopSpirit Airlines
20h 37mBOS-OAK
$572
6/15Sat
multi-stopSpirit Airlines
15h 44mOAK-BOS
6/19Wed
multi-stopSpirit Airlines
16h 58mBOS-OAK
$574
6/13Thu
multi-stopSun Country Air
7h 50mOAK-BOS
6/16Sun
multi-stopSun Country Air
14h 33mBOS-OAK
$725
6/15Sat
multi-stopAlaska Airlines
25h 52mOAK-BOS
6/16Sun
multi-stopAlaska Airlines
25h 21mBOS-OAK
$788
6/13Thu
multi-stopAlaska Airlines
9h 59mOAK-BOS
6/16Sun
multi-stopAlaska Airlines
19h 55mBOS-OAK
$912

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Oakland - Massachusetts Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Massachusetts - Oakland

Cabin classes: