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

Chicago → Oakland via Portland: arrives on time 27%

  1. 16:40 MDW → 19:00 PDX
    WN 4765 · Southwest · 4h 20m · 33% on time, 0.0% cancelled
  2. 3h 40m layover in Portland (PDX) · 45 min minimum on one ticket
  3. 22:40 PDX → 00:30 OAK +1 day
    WN 3205 · Southwest · 1h 45m · 29% on time, 0.0% cancelled

Total trip 9h 45m, scheduled departure to arrival (Oakland is 2 h behind Chicago). Times are local. Both flew on 24 of the last 56 days.

Makes the connection93%The first flight arrived more than 175 minutes late on 7% of the days it flew: too late for the 45-minute minimum connection on a 3h 40m layover.
Arrives on time27%First flight not cancelled (0.0% are) × connection made (93%) × second flight not cancelled (0.0% are) and within 15 minutes (29%).
Total trip9h 45mMDW 16:40 to OAK 00:30, 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.