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

Portland → Chicago via San Jose: arrives on time 93%

  1. 17:40 PDX → 19:32 SJC
    AS 2113 · Alaska, flown by Horizon · 1h 52m · 81% on time, 0.0% cancelled
  2. 3h 23m 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 20m, scheduled departure to arrival (Chicago is 2 h ahead of Portland). Times are local. Both flew on 47 of the last 56 days.

Makes the connection99%The first flight arrived more than 113 minutes late on 1% of the days it flew: too late for the 90-minute minimum connection on a 3h 23m layover.
Arrives on time93%First flight not cancelled (0.0% are) × connection made (99%) × second flight not cancelled (0.0% are) and within 15 minutes (94%).
Total trip9h 20mPDX 17:40 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.