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Find cheap flights from Oakland to Massachusetts from $76

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 8/27. 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
Sat 6/8
Sat 6/15

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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$154
West Tisbury
West Tisbury2 stops$492
Albany
Albany1 stop$551

Good to know

Low season

February

High season

June

Cheapest flight

$76
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

  • On average*, there is no price difference when choosing to fly in the morning or the evening on this flight route.
*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 10778 reviews
7.9Comfort
8.6Crew
7.4Food
8.0Entertainment
8.2Boarding
Airline reviews

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

6.0 GoodEliza, Apr 2024SAN - LAX
Read more about Delta reviews

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

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

You need to be a hacker to get the (Free) WiFi

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.

One hour late taking off. Concerning, very hard landing. Uncomfortable seats with no recline. Extremely slow baggage claim. Very professional, knowledgeable flight attendants. Brand new, very clean plane.

Can’t say there was anything I particularly liked. Seats were very tight, leather wrapped plastic. I followed up a much longer and cheaper trip from Honolulu on southwest, everything was phenomenal, this flight was the exact opposite. Blows my mind they charge for water of all things. One of the attendants seemed very rude, I watched a taller gentleman a couple rows forward with his knees pressed into the back of the seat ahead, while the woman in that seat leaned forward the entire flight, I’m sure because she could feel his knees. I’ll be avoiding spirit like the plague from here forward.

Didn’t make the connecting flight due to a delay on our first flight.

I had a phobia for Spirit and now is 100% confirmed. Flight delayed, missed connecting flight and staying overnight . Now not even able to get my boarding pass until I’ll get into the airport. It’s really really bad at this point

I felt scam to have to pay $50 additional for my carry on luggage which was free for my other airline.

Book cheap flights from Oakland to Massachusetts

Recent round-trip flight deals

9/21Sat
1 stopSpirit Airlines
9h 50mOAK-BOS
10/1Tue
1 stopSpirit Airlines
15h 32mBOS-OAK
$154
8/28Wed
1 stopSpirit Airlines
8h 15mOAK-BOS
9/5Thu
1 stopSpirit Airlines
14h 35mBOS-OAK
$159
5/29Wed
2 stopsSpirit Airlines
14h 36mOAK-BOS
6/5Wed
2 stopsSpirit Airlines
16h 19mBOS-OAK
$160
5/29Wed
2 stopsSpirit Airlines
14h 36mOAK-BOS
6/5Wed
3 stopsSpirit Airlines
20h 48mBOS-OAK
$167
6/6Thu
1 stop
7h 47mOAK-BOS
6/11Tue
2 stops
31h 42mBOS-OAK
$242
6/7Fri
1 stop
13h 09mOAK-BOS
6/11Tue
2 stops
32h 12mBOS-OAK
$244
6/10Mon
1 stopSun Country Air
13h 52mOAK-BOS
6/13Thu
1 stopSun Country Air
14h 27mBOS-OAK
$275
5/30Thu
1 stopSun Country Air
7h 34mOAK-BOS
6/2Sun
1 stopSun Country Air
14h 24mBOS-OAK
$299
7/16Tue
2 stopsDelta
14h 30mOAK-MVY
7/18Thu
2 stopsDelta
31h 40mMVY-OAK
$492
7/30Tue
2 stopsDelta
14h 30mOAK-MVY
8/7Wed
2 stopsDelta
36h 00mMVY-OAK
$610

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Recent one-way flight deals

8/27Tue
1 stopSpirit Airlines
8h 15mOAK-BOS
$76
8/28Wed
1 stopSpirit Airlines
8h 15mOAK-BOS
$84
6/10Mon
1 stopSun Country Air
13h 52mOAK-BOS
$130
6/7Fri
3 stops
24h 34mOAK-BOS
$131
6/16Sun
1 stopSun Country Air
8h 01mOAK-BOS
$133
5/18Sat
2 stops
19h 31mOAK-BOS
$167
5/29Wed
2 stopsAlaska Airlines
14h 05mOAK-BOS
$194
6/4Tue
1 stopAlaska Airlines
11h 26mOAK-BOS
$212
5/18Sat
1 stopDelta
8h 26mOAK-BOS
$244
5/18Sat
1 stopDelta
8h 26mOAK-BOS
$246

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Last minute flights from Oakland to Massachusetts

Last minute flight, train and bus deals

5/14Tue
multi-stopSpirit Airlines
12h 24mOAK-BOS
5/15Wed
multi-stopSpirit Airlines
29h 28mBOS-OAK
$392
5/14Tue
multi-stopSpirit Airlines
14h 15mOAK-BOS
6/9Sun
multi-stopSpirit Airlines
11h 50mBOS-OAK
$439
5/14Tue
multi-stopSpirit Airlines
14h 15mOAK-BOS
6/9Sun
multi-stopSpirit Airlines
11h 50mBOS-OAK
$493
5/14Tue
multi-stopSpirit Airlines
12h 24mOAK-BOS
5/15Wed
multi-stopSpirit Airlines
8h 40mBOS-OAK
$528
5/13Mon
multi-stopSpirit Airlines
23h 30mOAK-BOS
5/20Mon
multi-stopSpirit Airlines
8h 39mBOS-OAK
$542
5/14Tue
multi-stopSpirit Airlines
15h 26mOAK-BOS
5/17Fri
multi-stopSpirit Airlines
8h 39mBOS-OAK
$562
5/14Tue
multi-stopDelta
8h 26mOAK-BOS
5/15Wed
multi-stopDelta
8h 21mBOS-OAK
$638
5/10Fri
multi-stopAlaska Airlines
9h 59mOAK-BOS
5/13Mon
multi-stopAlaska Airlines
9h 31mBOS-OAK
$696
5/12Sun
multi-stopAlaska Airlines
20h 45mOAK-BOS
5/13Mon
multi-stopAlaska Airlines
9h 31mBOS-OAK
$842
5/12Sun
multi-stopAlaska Airlines
11h 04mOAK-BOS
5/13Mon
multi-stopAlaska Airlines
9h 31mBOS-OAK
$902

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Oakland - Massachusetts Flights

Departure:

Oakland (OAK)United States

Return flight deals:

Massachusetts - Oakland

Cabin classes: