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

Portland → Chicago via Phoenix: arrives on time 80%

  1. 17:51 PDX → 20:37 PHX
    AS 746 · Alaska · 2h 46m · 78% on time, 0.8% cancelled
  2. 3h 18m layover in Phoenix (PHX) · 90 min minimum on separate tickets
  3. 23:55 PHX → 05:10 MDW +1 day
    WN 3298 · Southwest · 3h 15m · 83% on time, 0.0% cancelled

Total trip 9h 19m, scheduled departure to arrival (Chicago is 2 h ahead of Portland). Times are local. Both flew on 26 of the last 56 days.

Makes the connection97%The first flight arrived more than 108 minutes late on 3% of the days it flew: too late for the 90-minute minimum connection on a 3h 18m layover.
Arrives on time80%First flight not cancelled (0.8% are) × connection made (97%) × second flight not cancelled (0.0% are) and within 15 minutes (83%).
Total trip9h 19mPDX 17:51 to MDW 05:10, 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.