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Find cheap flights from Oakland to Massachusetts from $79

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 8/20. 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
Thu 6/27
Thu 7/4

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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$157
West Tisbury
West Tisbury2 stops$1,173
Albany
Albany1 stop$698

Good to know

Low season

February

High season

June

Cheapest flight

$79
Best time to beat the crowds but there is an average 40% increase in price.
Most popular time to fly with an average 14% 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 13% more expensive 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 10502 reviews
8.2Boarding
7.4Food
8.0Entertainment
7.9Comfort
8.6Crew
Airline reviews

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!

10.0 ExcellentMichael, May 2024SJC - ATL
Read more about Delta reviews

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.

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Great, on time departure, friendly and accommodating crew, great leg room, Smith flight

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.

The seat was very uncomfortable from Boston to Nashville. Otherwise the flight was excellent.

Kayak does not know that spirit airlines charged me $70 to fly. But the bag check-in was $89 each way. This is false advertising to lure people. Spirit airlines sends bunch of emails after flight purchases to buy wifi, better seats, priority boarding, secure reserved seats. This is false advertising. Up front pricing. I would of flown jet blue or Alaska airlines.

Book cheap flights from Oakland to Massachusetts

Recent round-trip flight deals

8/22Thu
1 stopSpirit Airlines
15h 00mOAK-BOS
8/27Tue
2 stopsSpirit Airlines
30h 18mBOS-OAK
$157
8/22Thu
1 stopSpirit Airlines
15h 00mOAK-BOS
8/27Tue
1 stopSpirit Airlines
14h 35mBOS-OAK
$158
6/11Tue
2 stopsSpirit Airlines
16h 23mOAK-BOS
8/14Wed
1 stopSpirit Airlines
14h 35mBOS-OAK
$170
7/10Wed
2 stops
25h 23mOAK-BOS
7/15Mon
1 stop
13h 39mBOS-OAK
$258
7/9Tue
2 stops
25h 40mOAK-BOS
7/18Thu
1 stop
12h 07mBOS-OAK
$279
7/8Mon
1 stopSun Country Air
13h 36mOAK-BOS
7/15Mon
1 stopSun Country Air
13h 39mBOS-OAK
$320
6/17Mon
1 stopSun Country Air
13h 32mOAK-BOS
6/27Thu
1 stopSun Country Air
8h 51mBOS-OAK
$353
7/2Tue
1 stopDelta
8h 12mOAK-BOS
7/4Thu
1 stopDelta
9h 16mBOS-OAK
$377
6/10Mon
1 stopDelta
9h 00mOAK-BDL
6/12Wed
1 stopDelta
10h 17mBDL-OAK
$424
6/12Wed
3 stopsAmerican Airlines
20h 00mOAK-ALB
6/18Tue
2 stopsAmerican Airlines
20h 55mALB-OAK
$2,334

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Recent one-way flight deals

8/20Tue
1 stopSpirit Airlines
15h 00mOAK-BOS
$79
8/19Mon
2 stopsSpirit Airlines
17h 13mOAK-BOS
$80
8/19Mon
2 stopsSpirit Airlines
23h 23mOAK-BOS
$82
7/11Thu
1 stopSun Country Air
14h 36mOAK-BDL
$140
6/17Mon
1 stopSun Country Air
13h 32mOAK-BOS
$140
7/24Wed
1 stop
15h 56mOAK-BDL
$149
7/17Wed
2 stops
26h 33mOAK-BDL
$152
7/23Tue
1 stopDelta
8h 00mOAK-BOS
$199
6/15Sat
1 stopSouthwest
12h 25mOAK-BOS
$215
7/2Tue
1 stopDelta
8h 12mOAK-BOS
$229

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Last minute flights from Oakland to Massachusetts

Last minute flight, train and bus deals

6/2Sun
multi-stop
7h 34mOAK-BOS
6/5Wed
multi-stop
29h 53mBOS-OAK
$264
5/30Thu
multi-stop
9h 04mOAK-BOS
6/4Tue
multi-stop
32h 12mBOS-OAK
$269
5/30Thu
multi-stop
9h 04mOAK-BOS
6/4Tue
multi-stop
33h 25mBOS-OAK
$274
5/31Fri
multi-stopSpirit Airlines
29h 10mOAK-BOS
6/15Sat
multi-stopSpirit Airlines
20h 37mBOS-OAK
$282
6/2Sun
multi-stopSpirit Airlines
31h 54mOAK-BOS
6/5Wed
multi-stopSpirit Airlines
33h 41mBOS-OAK
$318
5/30Thu
multi-stopSun Country Air
9h 04mOAK-BOS
6/7Fri
multi-stopSun Country Air
8h 48mBOS-OAK
$397
6/2Sun
multi-stopSun Country Air
7h 34mOAK-BOS
6/9Sun
multi-stopSun Country Air
14h 31mBOS-OAK
$445
6/1Sat
multi-stopDelta
8h 26mOAK-BOS
6/2Sun
multi-stopDelta
8h 54mBOS-OAK
$575
5/30Thu
multi-stopDelta
8h 26mOAK-BOS
6/2Sun
multi-stopDelta
8h 54mBOS-OAK
$612
6/2Sun
multi-stopAlaska Airlines
9h 36mOAK-BOS
6/5Wed
multi-stopAlaska Airlines
9h 29mBOS-OAK
$698

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Oakland - Massachusetts Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Massachusetts - Oakland

Cabin classes: