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

Oakland → Chicago via Los Angeles: arrives on time 78%

  1. 20:12 OAK → 21:38 LAX
    WN 2396 · Southwest · 1h 25m · 50% on time, 0.0% cancelled
  2. 2h 17m layover in Los Angeles (LAX) · 45 min minimum on one ticket
  3. 23:55 LAX → 05:55 MDW +1 day
    WN 2413 · Southwest · 4h 00m · 86% on time, 1.7% cancelled

Total trip 7h 43m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 48 of the last 56 days.

Makes the connection92%The first flight arrived more than 92 minutes late on 8% of the days it flew: too late for the 45-minute minimum connection on a 2h 17m layover.
Arrives on time78%First flight not cancelled (0.0% are) × connection made (92%) × second flight not cancelled (1.7% are) and within 15 minutes (86%).
Total trip7h 43mOAK 20:12 to MDW 05:55, 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.