$134 Find Cheap Flights from Oakland to Massachusetts

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 1/7. 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
1 adult, Economy, 0 bags

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Massachusetts, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Massachusetts, as well as popular online travel agencies
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Cheap Flights from Oakland to Massachusetts

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Boston
Boston1 stop$267
Albany
Albany2 stops$367
Boston
Boston1 stop$267
Albany
Albany2 stops$367

Book Cheap Oakland to Massachusetts Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Oakland to Massachusetts that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Oakland to Massachusetts

Thu, Jan 29 - Tue, Feb 3
Alaska Airlines Logo
8:03 pm - 3:20 pm
OAK
-
BOS
16h 17m1 stop
Alaska Airlines Logo
5:20 pm - 9:46 am
BOS
-
OAK
19h 26m1 stop
$267Alaska Airlines
Thu, Jan 22 - Tue, Feb 3
Alaska Airlines Logo
11:43 am - 11:54 pm
OAK
-
BOS
9h 11m1 stop
Alaska Airlines Logo
7:00 am - 4:23 pm
BOS
-
OAK
12h 23m1 stop
$287Alaska Airlines
Thu, Jan 22 - Mon, Feb 2
Alaska Airlines Logo
11:43 am - 11:54 pm
OAK
-
BOS
9h 11m1 stop
Alaska Airlines Logo
7:00 am - 4:23 pm
BOS
-
OAK
12h 23m1 stop
$292Alaska Airlines
Wed, Jan 21 - Tue, Feb 3
Delta Logo
12:33 pm - 11:56 pm
OAK
-
BOS
8h 23m1 stop
Delta Logo
4:25 pm - 11:53 pm
BOS
-
OAK
10h 28m1 stop
$297Delta
Wed, Jan 21 - Tue, Feb 3
Delta Logo
12:33 pm - 11:56 pm
OAK
-
BOS
8h 23m1 stop
Delta Logo
3:05 pm - 11:53 pm
BOS
-
OAK
11h 48m2 stops
$302Delta
Sat, Jan 17 - Sat, Jan 24
Southwest Logo
5:55 am - 8:55 pm
OAK
-
BOS
12h 00m1 stop
Southwest Logo
6:05 am - 4:40 pm
BOS
-
OAK
13h 35m1 stop
$304Southwest
Wed, Jan 21 - Mon, Feb 2
Delta Logo
5:55 am - 7:10 pm
OAK
-
BOS
10h 15m2 stops
Delta Logo
4:58 pm - 11:53 pm
BOS
-
OAK
9h 55m2 stops
$307Delta
Tue, Jan 6 - Fri, Jan 9
Southwest Logo
9:40 am - 10:30 pm
OAK
-
BOS
9h 50m1 stop
Southwest Logo
4:50 pm - 10:15 pm
BOS
-
OAK
8h 25m1 stop
$322Southwest
Wed, Jan 21 - Tue, Jan 27
Southwest Logo
7:35 pm - 8:25 am
OAK
-
BDL
9h 50m2 stops
Southwest Logo
5:30 am - 2:35 pm
BDL
-
OAK
12h 05m2 stops
$335Southwest
Wed, Jan 21 - Tue, Jan 27
Southwest Logo
7:35 pm - 8:25 am
OAK
-
BDL
9h 50m2 stops
Southwest Logo
5:30 am - 2:05 pm
BDL
-
OAK
11h 35m1 stop
$336Southwest
Booking Insights

KAYAK's insights & trends for Oakland to Massachusetts flights

Get data-powered insights and trends into flights from Oakland to Massachusetts to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Oakland to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland to Massachusetts, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Oakland to Massachusetts is January, when tickets cost $296 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $486 and $477 respectively.

What’s the cheapest day of the week to fly from Oakland to Massachusetts?

The average price of all round-trip flights from Oakland to Massachusetts clicked on KAYAK for each day over the last 12 months.

For Oakland to Massachusetts, Saturday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Massachusetts back to Oakland, the best deals are generally found on Thursday, with Sunday being the most expensive.

How far in advance should I book a flight from Oakland to Massachusetts?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Oakland to Massachusetts, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Oakland to Massachusetts, you should book around 5 weeks before departure, which saves you about 35% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonDecember
Cheapest flight$134
Best time to beat the crowds but there is an average 19% increase in price.
Most popular time to fly with an average 12% 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 from Oakland to Massachusetts 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 from Oakland to Massachusetts with an airline and back 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 from Oakland to Massachusetts up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Massachusetts?

    The cheapest time of day to fly to Massachusetts is generally in the afternoon, when round-trip flights cost $327 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the evening, which is peak travel time and where the average cost of a ticket is $427.

Reviews of the top 4 airlines serving from Oakland to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from Oakland to Massachusetts. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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
Alaska AirlinesOverall score based on 11470 reviews
8.5Crew
8.1Boarding
7.8Comfort
7.1Food
7.0Entertainment
Airline reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

8.0 ExcellentEvie, Dec 2025
SAN - HNL
Read more Alaska Airlines reviews

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

The flight attendants were excellent and I was in the back of the plane. Much much better than recent JetBlue experiences on that route and better than Delta on that route.

I’m not sure there is anything that can be improved, even the cost was fantastic.

Poor. They should have given me a row with more room and instead they put me in a middle seat with two strangers next to me

They were so kind to us! The entire staff were so good to us when we had our service dog join our trip and we couldn't be more grateful!

Larger seats and more room would elevate the experience. Otherwise, it was good!

Flight crew and flight were good. But it departed two hours late.

They changed our flight from a one stop 3 hour layover to a non-stop. Saved us hours and got us there sooner.

The ground crew did not supply drink or snacks during the layover in SFO. So there weren't many options. Otherwise, it was all great.

No accommodation or credit offered for cancelled layover flight to Eugene from portland

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

Perfect flight both ways. On time, courteous staff, plane comfortable and cool. Best domestic flights I’ve had in awhile.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

we were delayed because of some safety check that wasn't done or available

Friendly crew. Poor food service maybe due to full flight. All in all, you get what you pay for.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

very difficult boarding process - aggressive passengers not the friendliest crew

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

The plane was late to leave.. Internet was lousy. TV was not working. when we arrived, We stayed on the plane for a long time before we got to the gate. It took us a long time to retrieve our luggage because they didn’t know what carousel to send them to. It was a bad experience.

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Everything you need to know for your flight from Oakland to Massachusetts

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