$118 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 3/4. 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$229
Albany
Albany2 stops$404
Boston
Boston1 stop$229
Albany
Albany2 stops$404

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

Tue, Mar 3 - Wed, Mar 4
Alaska Airlines Logo
5:31 pm - 6:54 am
OAK
-
BOS
10h 23m
1 stop
Alaska Airlines Logo
9:02 am - 4:37 pm
BOS
-
OAK
10h 35m
1 stop
$229Alaska Airlines
Wed, Feb 25 - Wed, Mar 4
Alaska Airlines Logo
10:04 am - 3:36 pm
OAK
-
BOS
26h 32m
1 stop
Alaska Airlines Logo
9:02 am - 4:37 pm
BOS
-
OAK
10h 35m
1 stop
$235Alaska Airlines
Fri, Feb 27 - Tue, Mar 3
Alaska Airlines Logo
6:15 am - 11:59 pm
OAK
-
BOS
14h 44m
1 stop
Alaska Airlines Logo
9:02 am - 4:37 pm
BOS
-
OAK
10h 35m
1 stop
$256Alaska Airlines
Tue, Feb 24 - Sat, Feb 28
Alaska Airlines Logo
6:15 am - 11:59 pm
OAK
-
BOS
14h 44m
1 stop
Alaska Airlines Logo
6:24 pm - 9:14 am
BOS
-
OAK
17h 50m
1 stop
$261Alaska Airlines
Thu, Feb 26 - Mon, Mar 2
Alaska Airlines Logo
6:15 am - 11:59 pm
OAK
-
BOS
14h 44m
1 stop
Alaska Airlines Logo
4:36 pm - 9:24 am
BOS
-
OAK
19h 48m
1 stop
$277Alaska Airlines
Mon, Mar 9 - Tue, Mar 10
Delta Logo
4:49 pm - 6:10 am
OAK
-
BOS
10h 21m
1 stop
Delta Logo
6:44 pm - 11:46 pm
BOS
-
OAK
8h 02m
1 stop
$297Delta
Thu, Feb 26 - Mon, Mar 2
Delta Logo
5:55 am - 8:11 pm
OAK
-
BOS
11h 16m
2 stops
Delta Logo
6:37 pm - 11:51 pm
BOS
-
OAK
8h 14m
1 stop
$302Delta
Mon, Mar 2 - Thu, Mar 5
Southwest Logo
6:20 pm - 8:10 am
OAK
-
ALB
10h 50m
2 stops
Southwest Logo
7:05 pm - 12:10 am
ALB
-
OAK
8h 05m
1 stop
$404Southwest
Mon, Mar 2 - Thu, Mar 5
Southwest Logo
6:20 pm - 8:10 am
OAK
-
ALB
10h 50m
2 stops
Southwest Logo
12:05 pm - 7:35 pm
ALB
-
OAK
10h 30m
2 stops
$409Southwest
Thu, Jun 18 - Mon, Jun 22
Multiple Airlines Logo
7:50 pm - 11:38 am
OAK
-
ACK
12h 48m
2 stops
Multiple Airlines Logo
9:40 am - 10:47 pm
ACK
-
OAK
16h 07m
2 stops
$1,621Multiple Airlines
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 September, when tickets cost $336 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $591 and $465 respectively.

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 seasonJanuary
Cheapest flight$118
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% 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.

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 11821 reviews
7.1Food
8.1Boarding
8.5Crew
7.8Comfort
7.0Entertainment
Airline reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

2.0 MediocreAnonymous, Jan 2026
STS - SAN
Read more Alaska Airlines reviews

Due to plane delays on both legs of my flight home, I had to be rerouted from Santa Rosa to Las Vegas on Skywest and then to DCA on American. SkyWest airlines sat on runway in Las Vegas for 20 minutes waiting for gate to clear. My boarding pass for American that I was given by Alaska was incomplete and the Las Vegas airport lacked signage and departure boards. I barely made my flight bc it was so confusing. American Airlines has a much better wireless connection. I’ll never fly Alaska again. It clearly has problems.

I paid for wifi and it never worked... it was miserable. I couldn't access my shared files to work on the plane, it didn't work on my phone. I paid for nothing but frustration and continual refreshing, hoping it would work

The stewardess are very nice and pleasant, Someone onboard had a medical attention, and they attended that person non-stop all throughout the flight, and yet, did not forget to serve and help other passengers.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

There is nothing critical to complain about but I would say the snacks are pretty bad Airline staff could be aggressive the way they move through the aisles and the plane I also got hustled for a small wallet size men bag and force the consolidated with my carry on item we're talking about a wallet size bag.

The bathroom trash container under the sink fell out and was like that long before my flight. The plane smelled of canned fish and floor was Deteriorating

My TSA pre check was left Off my boarding pass which was a large inconvenience.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

Overall it was fine, however one of my two checked bags did not arrive and I was told it was left in Palm Springs. I don't understand how one of the two bags made it through fine but the other got lost .

The Alaska Airlines app made it very difficult to find my boarding pass. It was very frustrating to use! The flight itself was flawless.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Great flight but super high price. Glad it was a business trip and not personal

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

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.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

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

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

Information on your arrival and departure airports