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Find cheap flights from Oakland to Massachusetts from $80

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
Fri 6/21
Fri 6/28

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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$184
West Tisbury
West Tisbury3 stops$1,012
Albany
Albany3 stops$467

Good to know

Low season

February

High season

June

Cheapest flight

$80
Best time to beat the crowds but there is an average 39% increase in price.
Most popular time to fly with an average 18% 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 40% 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 10583 reviews
8.2Boarding
8.6Crew
8.0Entertainment
7.4Food
7.9Comfort
Airline reviews

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

8.0 Excellentrghinftl, May 2024FLL - BOS
Read more about Delta reviews

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

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

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

8/28Wed
1 stopSpirit Airlines
15h 00mOAK-BOS
9/4Wed
2 stopsSpirit Airlines
17h 17mBOS-OAK
$184
8/19Mon
1 stopSpirit Airlines
15h 00mOAK-BOS
8/22Thu
1 stopSpirit Airlines
13h 31mBOS-OAK
$187
8/28Wed
1 stop
8h 15mOAK-BOS
9/4Wed
1 stop
10h 06mBOS-OAK
$234
6/7Fri
1 stop
13h 09mOAK-BOS
6/10Mon
2 stops
23h 29mBOS-OAK
$248
7/25Thu
1 stopSun Country Air
13h 40mOAK-BDL
8/8Thu
1 stopSun Country Air
8h 34mBDL-OAK
$329
6/2Sun
1 stopSun Country Air
7h 34mOAK-BOS
6/13Thu
1 stopSun Country Air
14h 27mBOS-OAK
$335
7/15Mon
1 stopDelta
8h 48mOAK-BDL
7/17Wed
2 stopsDelta
13h 51mBDL-OAK
$477
8/24Sat
2 stopsDelta
10h 03mOAK-ALB
8/27Tue
2 stopsDelta
9h 17mALB-OAK
$488
6/10Mon
3 stopsAmerican Airlines
20h 24mOAK-ALB
6/18Tue
2 stopsAmerican Airlines
16h 37mALB-OAK
$2,314
6/10Mon
3 stopsAmerican Airlines
20h 24mOAK-ALB
6/20Thu
2 stopsAmerican Airlines
14h 10mALB-OAK
$2,427

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Recent one-way flight deals

8/20Tue
1 stopSpirit Airlines
15h 00mOAK-BOS
$80
8/25Sun
1 stopSpirit Airlines
24h 50mOAK-BOS
$85
6/2Sun
1 stopSun Country Air
7h 07mOAK-BDL
$130
6/2Sun
1 stopSun Country Air
7h 34mOAK-BOS
$145
9/5Thu
1 stopDelta
9h 40mOAK-BOS
$148
6/26Wed
2 stops
26h 35mOAK-BDL
$152
9/6Fri
2 stopsDelta
10h 03mOAK-ALB
$153
7/3Wed
3 stops
33h 04mOAK-BDL
$158
6/4Tue
1 stopAlaska Airlines
11h 26mOAK-BOS
$190
6/3Mon
1 stopAlaska Airlines
9h 14mOAK-BOS
$193

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Last minute flights from Oakland to Massachusetts

Last minute flight, train and bus deals

5/23Thu
multi-stopDelta
7h 38mOAK-BOS
5/29Wed
multi-stopDelta
8h 21mBOS-OAK
$439
5/23Thu
multi-stopDelta
7h 38mOAK-BOS
5/31Fri
multi-stopDelta
8h 21mBOS-OAK
$492
5/23Thu
multi-stopDelta
8h 26mOAK-BOS
5/25Sat
multi-stopDelta
8h 59mBOS-OAK
$575
5/23Thu
multi-stopAlaska Airlines
9h 54mOAK-BOS
5/29Wed
multi-stopAlaska Airlines
12h 31mBOS-OAK
$597
5/23Thu
multi-stopSpirit Airlines
12h 47mOAK-BOS
5/25Sat
multi-stopSpirit Airlines
11h 19mBOS-OAK
$634
5/23Thu
multi-stopSpirit Airlines
26h 37mOAK-BOS
5/25Sat
multi-stopSpirit Airlines
8h 33mBOS-OAK
$650
5/23Thu
multi-stopAlaska Airlines
9h 54mOAK-BOS
5/31Fri
multi-stopAlaska Airlines
15h 42mBOS-OAK
$657
5/23Thu
multi-stop
36h 15mOAK-ALB
5/27Mon
multi-stop
35h 16mALB-OAK
$899
5/27Mon
multi-stop
24h 26mOAK-BDL
6/3Mon
multi-stop
23h 02mBDL-OAK
$918
5/24Fri
multi-stopAmerican Airlines
17h 14mOAK-BDL
5/27Mon
multi-stopAmerican Airlines
14h 31mBDL-OAK
$2,935

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Oakland - Massachusetts Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Massachusetts - Oakland

Cabin classes: