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

Oakland → Chicago via Portland: arrives on time 46%

  1. 20:30 OAK → 22:05 PDX
    WN 4368 · Southwest · 1h 35m · 29% on time, 0.0% cancelled
  2. 1h 25m layover in Portland (PDX) · 45 min minimum on one ticket
  3. 23:30 PDX → 05:20 MDW +1 day
    WN 3203 · Southwest · 3h 50m · 89% on time, 1.7% cancelled

Total trip 6h 50m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 40 of the last 56 days.

Makes the connection52%The first flight arrived more than 40 minutes late on 48% of the days it flew: too late for the 45-minute minimum connection on a 1h 25m layover.
Arrives on time46%First flight not cancelled (0.0% are) × connection made (52%) × second flight not cancelled (1.7% are) and within 15 minutes (89%).
Total trip6h 50mOAK 20:30 to MDW 05:20, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.