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

Portland → Chicago via San Jose: arrives on time 94%

  1. 17:20 PDX → 19:05 SJC
    WN 3210 · Southwest · 1h 45m · 62% on time, 0.0% cancelled
  2. 3h 50m layover in San Jose (SJC) · 45 min minimum on one ticket
  3. 22:55 SJC → 05:00 MDW +1 day
    WN 3886 · Southwest · 4h 05m · 94% on time, 0.0% cancelled

Total trip 9h 40m, scheduled departure to arrival (Chicago is 2 h ahead of Portland). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 185 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 50m layover.
Arrives on time94%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (94%).
Total trip9h 40mPDX 17:20 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.