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

San Jose → Chicago via Ontario: arrives on time 79%

  1. 20:15 SJC → 21:35 ONT
    WN 3692 · Southwest · 1h 18m · 45% on time, 0.0% cancelled
  2. 2h 20m layover in Ontario (ONT) · 45 min minimum on one ticket
  3. 23:55 ONT → 05:40 MDW +1 day
    WN 3153 · Southwest · 3h 45m · 83% on time, 0.0% cancelled

Total trip 7h 25m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 40 of the last 56 days.

Makes the connection95%The first flight arrived more than 95 minutes late on 5% of the days it flew: too late for the 45-minute minimum connection on a 2h 20m layover.
Arrives on time79%First flight not cancelled (0.0% are) × connection made (95%) × second flight not cancelled (0.0% are) and within 15 minutes (83%).
Total trip7h 25mSJC 20:15 to MDW 05:40, 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.