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

Chicago → Portland via San Diego: arrives on time 86%

  1. 05:52 MDW → 08:00 SAN
    WN 3103 · Southwest · 4h 08m · 94% on time, 0.0% cancelled
  2. 3h 04m layover in San Diego (SAN) · 90 min minimum on separate tickets
  3. 11:04 SAN → 13:43 PDX
    AS 576 · Alaska · 2h 39m · 88% on time, 1.7% cancelled

Total trip 9h 51m, scheduled departure to arrival (Portland is 2 h behind Chicago). Times are local. Both flew on 48 of the last 56 days.

Makes the connection100%The first flight arrived more than 94 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 04m layover.
Arrives on time86%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (1.7% are) and within 15 minutes (88%).
Total trip9h 51mMDW 05:52 to PDX 13:43, 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.