Southwest® flights from San Diego to Boston from $99

Promo Code

Low fares from San Diego to Boston

$

San Diego (SAN)to

Boston (BOS)
Depart: 09/30/2026

One-way

Basic

From
$99
Seen: 4 hrs ago

San Diego (SAN)to

Boston (BOS)
Depart: 09/29/2026

One-way

Basic

From
$99
Seen: 6 hrs ago

San Diego (SAN)to

Boston (BOS)
Depart: 09/01/2026

One-way

Basic

From
$99
Seen: 2 hrs ago

San Diego (SAN)to

Boston (BOS)
Depart: 09/08/2026

One-way

Basic

From
$99
Seen: 19 hrs ago

San Diego (SAN)to

Boston (BOS)
Depart: 10/20/2026

One-way

Basic

From
$99
Seen: 11 hrs ago

San Diego (SAN)to

Boston (BOS)
Depart: 09/12/2026

One-way

Basic

From
$99
Seen: 23 minutes ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from San Diego to Boston

Aug 2026
From$99*
Seen: 13 hrs ago
One Way/Basic
Sep 2026
From$99*
Seen: 19 hrs ago
One Way/Basic
Oct 2026
From$99*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $99
cmp-daily-histogram-bars-legend-max-price-aria-label $391
Displaying fares for August-2026
  • SAN–BOS: cmp-view-offers-disclaimer. Find Offers
    01

    Sat

    AUG

  • SAN–BOS, 08/02/2026: From $391
    02

    Sun

  • SAN–BOS, 08/03/2026: From $391
    03

    Mon

  • SAN–BOS, 08/04/2026: From $391
    04

    Tue

  • SAN–BOS, 08/05/2026: From $391
    05

    Wed

  • SAN–BOS, 08/06/2026: From $391
    06

    Thu

  • SAN–BOS: cmp-view-offers-disclaimer. Find Offers
    07

    Fri

  • SAN–BOS, 08/08/2026: From $296
    08

    Sat

  • SAN–BOS, 08/09/2026: From $296
    09

    Sun

  • SAN–BOS, 08/10/2026: From $296
    10

    Mon

  • SAN–BOS, 08/11/2026: From $296
    11

    Tue

  • SAN–BOS, 08/12/2026: From $296
    12

    Wed

  • SAN–BOS, 08/13/2026: From $296
    13

    Thu

  • SAN–BOS, 08/14/2026: From $199
    14

    Fri

  • SAN–BOS: cmp-view-offers-disclaimer. Find Offers
    15

    Sat

  • SAN–BOS, 08/16/2026: From $209
    16

    Sun

  • SAN–BOS, 08/17/2026: From $199
    17

    Mon

  • SAN–BOS, 08/18/2026: From $199
    18

    Tue

  • SAN–BOS, 08/19/2026: From $189
    19

    Wed

  • SAN–BOS, 08/20/2026: From $219
    20

    Thu

  • SAN–BOS, 08/21/2026: From $223
    21

    Fri

  • SAN–BOS, 08/22/2026: From $208
    22

    Sat

  • SAN–BOS, 08/23/2026: From $239
    23

    Sun

  • SAN–BOS, 08/24/2026: From $142
    24

    Mon

  • SAN–BOS, 08/25/2026: From $142
    25

    Tue

  • SAN–BOS, 08/26/2026: From $99
    26

    Wed

  • SAN–BOS, 08/27/2026: From $109
    27

    Thu

  • SAN–BOS, 08/28/2026: From $109
    28

    Fri

  • SAN–BOS, 08/29/2026: From $99
    29

    Sat

  • SAN–BOS, 08/30/2026: From $149
    30

    Sun

  • SAN–BOS, 08/31/2026: From $109
    31

    Mon

    • Range$99-$391

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    San Diego International Airport
    Arriving at:
    Logan International Airport
    Distance:
    2588 miles

    Route Information

    138† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 138 weekly flights from San Diego to Boston on Southwest Airlines.
    To find the lowest fares by day and time to fly San Diego to Boston with Southwest, check out our Low Fare Calendar.
    You can rent a car at Logan International Airport book yours with your flight.
    Yes! Flights from San Diego to Boston—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

    Explore Flights from Other Popular Origins

    Popular Flights from San Diego