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

Portland → Chicago via San Diego: arrives on time 78%

  1. 17:40 PDX → 20:18 SAN
    AS 369 · Alaska · 2h 38m · 57% on time, 3.9% cancelled
  2. 2h 22m layover in San Diego (SAN) · 90 min minimum on separate tickets
  3. 22:40 SAN → 04:40 MDW +1 day
    WN 257 · Southwest · 4h 00m · 92% on time, 0.0% cancelled

Total trip 9h 00m, scheduled departure to arrival (Chicago is 2 h ahead of Portland). Times are local. Both flew on 23 of the last 56 days.

Makes the connection88%The first flight arrived more than 52 minutes late on 12% of the days it flew: too late for the 90-minute minimum connection on a 2h 22m layover.
Arrives on time78%First flight not cancelled (3.9% are) × connection made (88%) × second flight not cancelled (0.0% are) and within 15 minutes (92%).
Total trip9h 00mPDX 17:40 to MDW 04:40, 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.