$129 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 9/30. 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

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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
Boston2 stops$239
Albany
Albany1 stop$277
Boston
Boston2 stops$239
Albany
Albany1 stop$277

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, Oct 16 - Mon, Oct 20
Spirit Airlines Logo
6:00 am - 7:00 pmOAK-BOS
10h 00m2 stops
Spirit Airlines Logo
4:59 pm - 7:38 amBOS-OAK
17h 39m2 stops
$239Spirit Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
Spirit Airlines Logo
6:00 am - 11:23 pmOAK-BDL
14h 23m2 stops
Spirit Airlines Logo
6:45 am - 11:27 pmBDL-OAK
19h 42m2 stops
$246Spirit Airlines
Find Deal
Fri, Dec 12 - Wed, Dec 17
Southwest Logo
6:50 am - 7:15 pmOAK-BOS
9h 25m1 stop
Southwest Logo
6:45 am - 1:55 pmBOS-OAK
10h 10m2 stops
$273Southwest
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Thu, Nov 6 - Mon, Nov 10
Southwest Logo
5:35 am - 6:00 pmOAK-ALB
9h 25m1 stop
Southwest Logo
6:45 pm - 12:05 amALB-OAK
8h 20m1 stop
$277Southwest
Find Deal
Thu, Sep 4 - Tue, Sep 9
Alaska Airlines Logo
7:07 pm - 6:00 amOAK-BOS
7h 53m1 stop
Alaska Airlines Logo
7:20 am - 1:36 pmBOS-OAK
9h 16m1 stop
$278Alaska Airlines
Find Deal
Tue, Sep 9 - Sat, Sep 13
Alaska Airlines Logo
11:01 am - 12:27 amOAK-BOS
10h 26m1 stop
Alaska Airlines Logo
6:00 am - 7:18 pmBOS-OAK
16h 18m1 stop
$282Alaska Airlines
Find Deal
Wed, Sep 3 - Sat, Sep 6
Delta Logo
12:35 pm - 11:58 pmOAK-BOS
8h 23m1 stop
Delta Logo
5:20 pm - 10:46 pmBOS-OAK
8h 26m1 stop
$297Delta
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Wed, Sep 3 - Tue, Sep 9
Delta Logo
12:35 pm - 11:58 pmOAK-BOS
8h 23m1 stop
Delta Logo
6:05 am - 4:16 pmBOS-OAK
13h 11m2 stops
$302Delta
Find Deal
Thu, Aug 21 - Mon, Aug 25
 Logo
6:00 am - 10:34 pmOAK-BOS
13h 34m2 stops
 Logo
10:39 am - 11:27 pmBOS-OAK
15h 48m2 stops
Thu, Oct 2 - Sun, Oct 5
 Logo
6:30 am - 10:35 amOAK-BDL
25h 05m3 stops
 Logo
6:00 am - 1:34 pmBDL-OAK
10h 34m1 stop
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 August, when tickets cost $360 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $477 and $457 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 3 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonJanuary
Cheapest flight$129
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 4% 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 5 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 10000 reviews
7.1Entertainment
7.8Comfort
8.1Boarding
7.1Food
8.5Crew
Airline reviews

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

4.0 OkaySean, Jul 2025SBP - SAN
Read more Alaska Airlines reviews

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

I always heard this was a terrible airline but I was happy to experience otherwise. The seats were more comfortable than delta. They did board late and gate was a little chaotic, which is to be expected for a budget airline. I would definitely do it again for that price.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Canceled flight. No communication of this prior. Rescheduled to next day. Our good seats we purchased months ago turned into last row middle. No apology, reason, nor compensation for time and $ spent.

delayed flight 3 hours, then took 45 min to get to gate and another 10 min to open door

Delayed flight both ways. Then, on the return flight, we were stuck on the tarmac for at least 30+ minutes. Idk what happened, but this was a bad experience.

The plane was put out of service and had to wait for a new plane to be assigned. No one had any information and the information on the screens was never updated. The call wait time was 2 hours and the estimated time for text assistance was 55 minutes which was a lie because after 55 minutes nothing happened. I understand that delays happen but to not have anyone available to provide any update or reassurance was just negligent. Also, what is the point of having an 800 number if no one answers it and don’t get me started on the text message system. Ridiculous!

Great flight, no bumps to speak of, pleasant crew, good inflight entertainment choices

Coffee or tea service would be nice for an evening flight, water or juice not good enough.

Very expensive for short flights. Can’t communicate with Alaska Air about passport issue at check-in. Also no replies to my text messages. Wanted to extend our vacation for two more days but this expensive flight ticket is called SAVER and I couldn’t make changes or cancel or get a credit even, so I paid another airline for the return trip. Extremely disappointed.

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 trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

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.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

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.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

It was too hot in the cabin. The AC did not help.

Love the mosaic program, being able to move to an extra space seat for free is awesome

Smooth boarding and friendly crew. Unfortunately as soon as we boarded the unit that provides air circulation failed. The pilot informed us and requested maintenance technicians to check it out. The plane became uncomfortably warm without any fresh air coming in. Plus the repair delayed our departure. I am glad the maintenance crew were able to fix the problem. I also was without use of my tv monitor for the first 1/3rd of the trip.

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

Had a issue with catching flight due to airline, was unable to board flight

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

I liked how cheap it was but both my flights were delayed heavily

It was okay delay was long but I made it

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

First off, i received an e-mail to allow me to check in for our flight. I folllowed the link, when it came to the seat selection, I was unable to select any "free" seats ( meaning without any additional charge) because everything was " unavailable". My Husband and I were ttavelling with our 3 children hence, i wanted to be assured that we were all seated next to each other. I tried 3 times and everytime I click the selection it said " error loading". What the system wants is for me to buy the seats ( anywhere from $25 to $50 dollars each passenger) like I did on our flight bound to L.A. I called customer service and the guy was unhelpful all he kept repeating was to come really early at the airport and we will be assigned seats there. Imagine my anxiety!!! Spirit says they are a budget airline but they are actually the opposite!! And just before our flight, the flight attendant KEPT announcing/ selling the seats that were not purchased for a cheaper price!! Like it was a bidding/ bargaining game! This was our first and last time to fly Spirit.

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