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

San Jose → Chicago via Portland: arrives on time 86%

  1. 18:37 SJC → 20:29 PDX
    AS 3030 · Alaska, flown by SkyWest · 1h 52m · 75% on time, 0.0% cancelled
  2. 3h 01m layover in Portland (PDX) · 90 min minimum on separate tickets
  3. 23:30 PDX → 05:20 MDW +1 day
    WN 3203 · Southwest · 3h 50m · 89% on time, 1.7% cancelled

Total trip 8h 43m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 48 of the last 56 days.

Makes the connection98%The first flight arrived more than 91 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 3h 01m layover.
Arrives on time86%First flight not cancelled (0.0% are) × connection made (98%) × second flight not cancelled (1.7% are) and within 15 minutes (89%).
Total trip8h 43mSJC 18:37 to MDW 05:20, 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.