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

Chicago → Oakland via San Diego: arrives on time 81%

  1. 05:52 MDW → 08:00 SAN
    WN 3103 · Southwest · 4h 08m · 94% on time, 0.0% cancelled
  2. 1h 50m layover in San Diego (SAN) · 45 min minimum on one ticket
  3. 09:50 SAN → 11:25 OAK
    WN 4166 · Southwest · 1h 35m · 81% on time, 0.0% cancelled

Total trip 7h 33m, scheduled departure to arrival (Oakland is 2 h behind Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection100%The first flight arrived more than 65 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 1h 50m layover.
Arrives on time81%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (81%).
Total trip7h 33mMDW 05:52 to OAK 11:25, 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.