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$110+ Cheap flights from San Diego (SAN) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from San Diego to Massachusetts

Keep the following information in mind while searching for San Diego to Massachusetts flight deals. Data was last updated September 11, 2025.

Round-trip from

$166
(Southwest)

One-way from

$110
(Southwest)

Popular in

December

Cheapest in

January

Average price

$343

Good round-trip deal

$257 or less

Good one-way deal

$171 or less
From San Diego to Massachusetts
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One-way flight from San Diego to Massachusetts
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Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from San Diego to Massachusetts.
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Price to beat on a one-way flight from San Diego to Massachusetts.
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Find flight deals from San Diego to Massachusetts

Cheapest flights from San Diego to Massachusetts
Explore the most affordable flight options available from San Diego to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/119:45 pmSAN - BOS
1 stop7h 30mSouthwest
Sat 11/154:45 pmBOS - SAN
1 stop8h 05mSouthwest
Deal found 9/10$169
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:00 amSAN - BOS
1 stop9h 35mSouthwest
Tue 12/96:00 pmBOS - SAN
1 stop8h 25mSouthwest
Deal found 9/10$174
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/109:45 pmSAN - BOS
1 stop8h 55mSouthwest
Wed 11/126:00 pmBOS - SAN
1 stop8h 25mSouthwest
Deal found 9/9$180
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/296:25 pmSAN - BOS
1 stop11h 55mSouthwest
Sat 11/15:20 amBOS - SAN
1 stop8h 30mSouthwest
Deal found 9/10$187
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/19:10 pmSAN - BOS
1 stop8h 05mSouthwest
Sat 10/45:05 amBOS - SAN
1 stop8h 30mSouthwest
Deal found 9/10$209
This Southwest deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/256:35 amSAN - BOS
1 stop11h 15mSouthwest
Sat 11/15:20 amBOS - SAN
1 stop8h 30mSouthwest
Deal found 9/9$210
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/76:40 amSAN - BOS
1 stop7h 35mSouthwest
Tue 12/96:00 pmBOS - SAN
1 stop8h 25mSouthwest
Deal found 9/10$212
This Southwest deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:35 amSAN - BDL
1 stop7h 55mSouthwest
Tue 10/286:05 pmBDL - SAN
1 stop7h 40mSouthwest
Deal found 9/10$229
This Southwest deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/219:10 pmSAN - BDL
1 stop8h 10mSouthwest
Sat 11/13:45 pmBDL - SAN
1 stop7h 50mSouthwest
Deal found 9/8$246
This American Airlines deal was found by Cheapflights users on 9/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/3010:45 pmSAN - ALB
1 stop10h 25mAmerican Airlines
Tue 10/76:01 amALB - SAN
1 stop9h 03mAmerican Airlines
Deal found 9/11$260
This Priceline deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/611:25 amSAN - BDL
1 stop9h 36mJetBlue
Mon 12/87:00 amBDL - SAN
1 stop10h 06mJetBlue
Deal found 9/10$261
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/310:45 pmSAN - ORH
1 stop14h 13mAmerican Airlines
Fri 10/314:17 pmORH - SAN
1 stop21h 57mAmerican Airlines
Deal found 9/10$262

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
Use the filters below to find and compare flights from San Diego to Massachusetts that are best for you.

Fly from

San Diego

Fly to

Massachusetts

Route

Depart

Return

Price

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Wed 10/29

6:25 pm-9:20 am

1 stop11h 55m

Boston Logan Intl

Sat 11/1

5:20 am-10:50 am

1 stop8h 30m

$187

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Mon 11/10

8:05 pm-8:15 am

2 stops9h 10m

Boston Logan Intl

Wed 11/12

8:30 am-9:05 pm

2 stops15h 35m

$220

San DiegoHartford

SAN - BDL

SANBDL

San Diego

Wed 10/22

7:05 pm-8:15 am

2 stops10h 10m

Hartford Bradley Intl

Tue 10/28

12:55 pm-7:55 pm

2 stops10h 00m

$239

San DiegoHartford

SAN - BDL

SANBDL

San Diego

Tue 10/21

9:10 pm-8:20 am

1 stop8h 10m

Hartford Bradley Intl

Sat 11/1

3:45 pm-8:35 pm

1 stop7h 50m

$246

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Tue 10/28

10:15 pm-6:53 am

Nonstop5h 38m

Boston Logan Intl

Sat 11/1

5:25 pm-8:44 pm

Nonstop6h 19m

$247

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Sat 10/25

10:15 pm-6:53 am

Nonstop5h 38m

Boston Logan Intl

Sat 11/1

5:25 pm-8:44 pm

Nonstop6h 19m

$247

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Wed 10/29

9:15 am-5:55 pm

Nonstop5h 40m

Boston Logan Intl

Sat 11/1

6:59 pm-9:40 am

1 stop17h 41m

$257

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Fri 11/7

2:05 pm-12:05 am

1 stop7h 00m

Boston Logan Intl

Mon 11/10

6:10 am-11:35 am

1 stop8h 25m

$261

San DiegoWorcester

SAN - ORH

SANORH

San Diego

Fri 10/3

10:45 pm-3:58 pm

1 stop14h 13m

Worcester

Fri 10/31

4:17 pm-11:14 am

1 stop21h 57m

$262

San DiegoBoston

SAN - BOS

SANBOS

San Diego

Fri 10/24

9:35 pm-6:20 am

Nonstop5h 45m

Boston Logan Intl

Thu 10/30

3:45 pm-7:16 pm

Nonstop6h 31m

$267

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/8

Showing 1-10 of 60 results
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Best time to book a flight from San Diego to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from San Diego with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from San Diego to Massachusetts

What is the cheapest month to book a flight from San Diego to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from San Diego to Massachusetts (average of $218). Flying from San Diego to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SAN to MA?

Find hourly flight availability from San Diego to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

When flying from San Diego to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from San Diego to Massachusetts

Explore weekly flight availability from San Diego to Massachusetts. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 11, 2025.

The most flights from SAN to USMA are scheduled on a Thursday (18 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated September 11, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Delta, and Hawaiian Airlines from San Diego to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Delta
8.0
Very good
7,960 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
Hawaiian Airlines
7.8
Good
2,723 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.
JetBlue
7.2
Good
2,913 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Boarding

8.1

Overall

8.0

Entertainment

7.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
6.0
Good

Hannah,Aug 2025

SFO - SAN

Ticket said TSA pre check, but then the TSA agent said that Alaska Airlines has not actually entered the pre check information for the ticket, so I had to use regular security. During boarding, I have a disability and need to board early. The Alaska Airlines employee announced disability boarding, but then immediately announced 2 other groups to board, so I still had to fight the crowds. On the plane, the stewardess was brusk and rude. Seats were very uncomfortable, especially on lower back.

Related info for your journey

Find useful and relevant information for your journey from San Diego to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San Diego to Massachusetts?

    Located just 2.6 mi from the city center, San Diego (SAN) is the airport most travelers will use when flying to Massachusetts from San Diego.

  • How popular is this San Diego to Massachusetts flight route?

    Flights from San Diego to Massachusetts have been viewed 16 times in the past calendar month.

  • How long is the flight from San Diego to Massachusetts?

    There are many flights that can get you from San Diego to Massachusetts in 5h 28m. Fly via Southwest, JetBlue, or Hawaiian Airlines to get the fastest option. The distance from San Diego to Massachusetts is about 2581 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from San Diego to Massachusetts one-way?

    One-way options have recently been found by users for as low as $110 on Southwest. Other airlines that offer cheap prices include Frontier from $116 and United Airlines from $129 one-way.

  • What are the most popular routes from San Diego to Massachusetts?

    While some choose either San Diego - Hartford Bradley Intl or San Diego - Albany Intl, San Diego - Boston Logan Intl is the most popular route from San Diego to Massachusetts.

  • What are the most reliable airlines from San Diego to Massachusetts?

    No one likes to see their flight delayed. When booking a flight from San Diego to Massachusetts consider choosing KLM (100%), Air France (91%) or Japan Airlines (90%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from San Diego to Massachusetts?

    On average you can expect to pay $696 for a flight from San Diego to Massachusetts. The cheapest flight overall is $118 while the most popular route, (San Diego - Boston Logan Intl) is currently priced at $166.

  • Can I find deals for flights from San Diego to Massachusetts that include hotel bookings?

    Yes. In addition to deals on San Diego to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Diego to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Diego to Massachusetts.

  • Can I find deals for business class flights from San Diego to Massachusetts?

    Yes. Cheapflights offers flight deals from San Diego to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San Diego to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from San Diego to Massachusetts (average of $218). Flying from San Diego to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for San Diego to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 9 airlines flying from San Diego to Massachusetts

Discover the top 9 airlines that operate flights from San Diego to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$65Average$168FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$118Average$260FlexibilityNo cancel feeOn-time65%
Hawaiian AirlinesCheapest$138Average$346FlexibilityNo cancel feeOn-time85%
DeltaCheapest$152Average$356FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$173Average$361FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$243Average$351FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$256Average$439FlexibilityNo cancel feeOn-time69%
Alaska AirlinesCheapest$256Average$445FlexibilityNo cancel feeOn-time75%
SouthwestCheapest$269Average$443FlexibilityNo cancel feeOn-time63%

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