Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
San Jose → Chicago via San Diego: arrives on time 32%
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14:58 SJC → 16:22 SANWN 3701 · Southwest · 1h 25m · 46% on time, 0.0% cancelled
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1h 08m layover in San Diego (SAN) · 45 min minimum on one ticket
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17:30 SAN → 23:25 MDWWN 3448 · Southwest · 3h 55m · 50% on time, 0.0% cancelled
Total trip 6h 27m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 32 of the last 56 days.
Makes the connection64%The first flight arrived more than 23 minutes late on 36% of the days it flew: too late for the 45-minute minimum connection on a 1h 08m layover.
Arrives on time32%First flight not cancelled (0.0% are) × connection made (64%) × second flight not cancelled (0.0% are) and within 15 minutes (50%).
Total trip6h 27mSJC 14:58 to MDW 23:25, layover included
Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.
Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.