$159 Find Cheap Flights from San Luis Obispo 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 San Luis Obispo to Massachusetts departing on 12/16. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Massachusetts

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

Mon, Dec 8 - Mon, Dec 15
American Airlines Logo
9:55 am - 11:56 pmSBP-BDL
11h 01m2 stops
American Airlines Logo
8:52 am - 6:29 pmBDL-SBP
12h 37m2 stops
$319American Airlines
Find Deal
Fri, Jan 16 - Tue, Jan 20
American Airlines Logo
1:03 pm - 11:30 pmSBP-BOS
7h 27m1 stop
American Airlines Logo
12:29 pm - 6:30 pmBOS-SBP
9h 01m1 stop
$351American Airlines
Find Deal
Mon, Dec 8 - Mon, Dec 15
American Airlines Logo
12:28 pm - 10:59 pmSBP-BDL
7h 31m1 stop
American Airlines Logo
8:52 am - 6:29 pmBDL-SBP
12h 37m2 stops
$354American Airlines
Find Deal
Fri, Jan 16 - Tue, Jan 20
American Airlines Logo
7:08 pm - 9:29 amSBP-BOS
11h 21m2 stops
American Airlines Logo
12:29 pm - 6:30 pmBOS-SBP
9h 01m1 stop
$357American Airlines
Find Deal
Fri, Jan 16 - Tue, Jan 20
American Airlines Logo
7:08 pm - 9:12 amSBP-BOS
11h 04m2 stops
American Airlines Logo
7:00 am - 3:39 pmBOS-SBP
11h 39m2 stops
$362American Airlines
Find Deal
Mon, Dec 15 - Wed, Dec 17
United Airlines Logo
5:02 am - 3:42 pmSBP-BOS
7h 40m1 stop
United Airlines Logo
11:55 am - 7:49 pmBOS-SBP
10h 54m2 stops
$371United Airlines
Find Deal
Sat, Mar 7 - Tue, Mar 10
United Airlines Logo
6:00 pm - 8:39 amSBP-BDL
11h 39m2 stops
United Airlines Logo
3:25 pm - 9:33 pmBDL-SBP
9h 08m1 stop
$414United Airlines
Find Deal
Sat, Mar 7 - Tue, Mar 10
United Airlines Logo
6:00 pm - 8:39 amSBP-BDL
11h 39m2 stops
United Airlines Logo
3:25 pm - 11:59 pmBDL-SBP
11h 34m2 stops
$419United Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 1
Alaska Airlines Logo
6:00 am - 5:52 pmSBP-BOS
8h 52m1 stop
Alaska Airlines Logo
6:30 am - 7:05 pmBOS-SBP
15h 35m2 stops
$439Alaska Airlines
Find Deal
Tue, Dec 16 - Thu, Jan 1
Alaska Airlines Logo
6:00 am - 5:52 pmSBP-BOS
8h 52m1 stop
Alaska Airlines Logo
6:30 am - 11:39 pmBOS-SBP
20h 09m1 stop
$440Alaska Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for San Luis Obispo to Massachusetts flights

Get data-powered insights and trends into flights from San Luis Obispo 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 San Luis Obispo to Massachusetts?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Luis Obispo 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 San Luis Obispo to Massachusetts is June, when tickets cost $419 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $637 and $601 respectively.

What’s the cheapest day of the week to fly from San Luis Obispo to Massachusetts?

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

When flying from San Luis Obispo to Massachusetts, you should consider leaving on a Thursday and avoid Mondays if you are looking for the best rates. For your return to San Luis Obispo, you’ll find the best rates on Saturdays and the most expensive ones on Sundays.

How far in advance should I book a flight from San Luis Obispo 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 San Luis Obispo 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 San Luis Obispo to Massachusetts, you should book around 4 weeks before departure, which saves you about 48% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$159
Most popular time to fly and prices are also 10% lower on average.
Flight from San Luis Obispo to Boston

FAQs - booking Massachusetts flights

  • How does KAYAK find such low prices on flights from San Luis Obispo 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 San Luis Obispo to Massachusetts.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Luis Obispo to Massachusetts?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Luis Obispo 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 San Luis Obispo 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 San Luis Obispo 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 San Luis Obispo 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 San Luis Obispo 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 at night, when round-trip flights cost $518 on average. Morning departures are around 9% more expensive than evening flights, on average. The most expensive time of day to fly to Massachusetts is generally in the morning, which is peak travel time and where the average cost of a ticket is $617.

Reviews of the top 3 airlines serving from San Luis Obispo to Massachusetts

 
See real verified KAYAK customer reviews for airlines flying from San Luis Obispo 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 San Luis Obispo 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 11281 reviews
7.1Food
8.1Boarding
7.8Comfort
8.5Crew
7.0Entertainment
Airline reviews

You need a n/a category. Too short a flight for food. I love flying on Alaska from Santa Rosa Airport!

10.0 ExcellentAnonymous, Nov 2025LAX - STS
Read more Alaska Airlines reviews

You need a n/a category. Too short a flight for food. I love flying on Alaska from Santa Rosa Airport!

I didn’t order food so can’t really say how it was. Overall, it was a great experience.

I've never flied them before but liked them. Weather was bad so a little scarey but they did a great job landing.

If they actually let me fly. I was rerouted to United and there was no Alaska airlines reps at all. Then the lady who worked the delta counter told me to go away and figure things out myself. Horrible experience.

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

Kayak I had marked one carry on, one checked bag. Yet when it completed the purchase marked it as no carry on. Fail on kayaks side! Then extended flight delayed due to computer issues. Crew of the plane did awesome but fail on both kayak and alaskan

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

Older aircraft, no meal, only food was for purchase. Not impressed United.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

Premium Plus is a really good idea for longer flights

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

The flight was flawless and we even arrived between 20 and 25 minutes early!

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

Very crowded flight but what can you expect these days?? Crew was accommodating.

They only offered water for Group 6. Awful announcements from the Crew. Couldn't understand a single word. Barely came by for the trash afterwards. Man, I love water for a premium flight. Wow. Water in a cup.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

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