tailodds FORECAST
Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

San Diego → Chicago via San Jose: arrives on time 58%

  1. 08:10 SAN → 09:42 SJC
    WN 3537 · Southwest · 1h 32m · 90% on time, 0.0% cancelled
  2. 58m layover in San Jose (SJC) · 45 min minimum on one ticket
  3. 10:40 SJC → 16:45 MDW
    WN 4357 · Southwest · 4h 05m · 65% on time, 0.0% cancelled

Total trip 6h 35m, scheduled departure to arrival (Chicago is 2 h ahead of San Diego). Times are local. Both flew on 48 of the last 56 days.

Makes the connection90%The first flight arrived more than 13 minutes late on 10% of the days it flew: too late for the 45-minute minimum connection on a 58m layover.
Arrives on time58%First flight not cancelled (0.0% are) × connection made (90%) × second flight not cancelled (0.0% are) and within 15 minutes (65%).
Total trip6h 35mSAN 08:10 to MDW 16:45, 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.