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

San Jose → Chicago via San Diego: arrives on time 85%

  1. 17:45 SJC → 19:10 SAN
    WN 3526 · Southwest · 1h 25m · 44% on time, 0.0% cancelled
  2. 3h 30m layover in San Diego (SAN) · 45 min minimum on one ticket
  3. 22:40 SAN → 04:40 MDW +1 day
    WN 257 · Southwest · 4h 00m · 92% on time, 0.0% cancelled

Total trip 8h 55m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 24 of the last 56 days.

Makes the connection92%The first flight arrived more than 165 minutes late on 8% of the days it flew: too late for the 45-minute minimum connection on a 3h 30m layover.
Arrives on time85%First flight not cancelled (0.0% are) × connection made (92%) × second flight not cancelled (0.0% are) and within 15 minutes (92%).
Total trip8h 55mSJC 17:45 to MDW 04:40, 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.