Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
San Diego → Boston via Chicago: arrives on time 28%
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12:10 SAN → 18:10 MDWWN 4163 · Southwest · 4h 00m · 50% on time, 2.4% cancelled
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1h 25m layover in Chicago (MDW) · 45 min minimum on one ticket
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19:35 MDW → 22:52 BOSWN 232 · Southwest · 2h 18m · 39% on time, 11.5% cancelled
Total trip 7h 43m, scheduled departure to arrival (Boston is 3 h ahead of San Diego). Times are local. Both flew on 24 of the last 56 days.
Makes the connection82%The first flight arrived more than 40 minutes late on 18% of the days it flew: too late for the 45-minute minimum connection on a 1h 25m layover.
Arrives on time28%First flight not cancelled (2.4% are) × connection made (82%) × second flight not cancelled (11.5% are) and within 15 minutes (39%).
Total trip7h 43mSAN 12:10 to BOS 22:52, layover included
Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.