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

Oakland → Chicago via Portland: arrives on time 73%

  1. 19:13 OAK → 20:50 PDX
    AS 2096 · Alaska, flown by Horizon · 1h 37m · 32% on time, 6.7% cancelled
  2. 2h 40m 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 07m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 30 of the last 56 days.

Makes the connection89%The first flight arrived more than 70 minutes late on 11% of the days it flew: too late for the 90-minute minimum connection on a 2h 40m layover.
Arrives on time73%First flight not cancelled (6.7% are) × connection made (89%) × second flight not cancelled (1.7% are) and within 15 minutes (89%).
Total trip8h 07mOAK 19:13 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.