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

Oakland → Chicago via Portland: arrives on time 62%

  1. 07:52 OAK → 09:29 PDX
    AS 2298 · Alaska, flown by Horizon · 1h 37m · 96% on time, 0.0% cancelled
  2. 2h 21m layover in Portland (PDX) · 90 min minimum on separate tickets
  3. 11:50 PDX → 17:45 MDW
    WN 3202 · Southwest · 3h 55m · 63% on time, 0.0% cancelled

Total trip 7h 53m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 37 of the last 56 days.

Makes the connection98%The first flight arrived more than 51 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 2h 21m layover.
Arrives on time62%First flight not cancelled (0.0% are) × connection made (98%) × second flight not cancelled (0.0% are) and within 15 minutes (63%).
Total trip7h 53mOAK 07:52 to MDW 17:45, 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.