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

Chicago → San Jose via Portland: arrives on time 92%

  1. 10:05 MDW → 12:25 PDX
    WN 2809 · Southwest · 4h 20m · 84% on time, 0.0% cancelled
  2. 2h 05m layover in Portland (PDX) · 90 min minimum on separate tickets
  3. 14:30 PDX → 16:25 SJC
    AS 3210 · Alaska, flown by SkyWest · 1h 55m · 96% on time, 0.0% cancelled

Total trip 8h 20m, scheduled departure to arrival (San Jose is 2 h behind Chicago). Times are local. Both flew on 45 of the last 56 days.

Makes the connection96%The first flight arrived more than 35 minutes late on 4% of the days it flew: too late for the 90-minute minimum connection on a 2h 05m layover.
Arrives on time92%First flight not cancelled (0.0% are) × connection made (96%) × second flight not cancelled (0.0% are) and within 15 minutes (96%).
Total trip8h 20mMDW 10:05 to SJC 16:25, 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.