tailodds FORECAST
Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

San Diego → Chicago via San Jose: arrives on time 90%

  1. 17:37 SAN → 19:11 SJC
    AS 3068 · Alaska, flown by SkyWest · 1h 34m · 70% on time, 2.0% cancelled
  2. 3h 44m layover in San Jose (SJC) · 90 min minimum on separate tickets
  3. 22:55 SJC → 05:00 MDW +1 day
    WN 3886 · Southwest · 4h 05m · 94% on time, 0.0% cancelled

Total trip 9h 23m, scheduled departure to arrival (Chicago is 2 h ahead of San Diego). Times are local. Both flew on 44 of the last 56 days.

Makes the connection98%The first flight arrived more than 134 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 3h 44m layover.
Arrives on time90%First flight not cancelled (2.0% are) × connection made (98%) × second flight not cancelled (0.0% are) and within 15 minutes (94%).
Total trip9h 23mSAN 17:37 to MDW 05:00, 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.