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

Oakland → Chicago via Las Vegas: arrives on time 72%

  1. 20:15 OAK → 21:52 LAS
    WN 5051 · Southwest · 1h 38m · 32% on time, 3.8% cancelled
  2. 2h 03m layover in Las Vegas (LAS) · 45 min minimum on one ticket
  3. 23:55 LAS → 05:25 MDW +1 day
    WN 2276 · Southwest · 3h 30m · 84% on time, 0.0% cancelled

Total trip 7h 10m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 24 of the last 56 days.

Makes the connection89%The first flight arrived more than 78 minutes late on 11% of the days it flew: too late for the 45-minute minimum connection on a 2h 03m layover.
Arrives on time72%First flight not cancelled (3.8% are) × connection made (89%) × second flight not cancelled (0.0% are) and within 15 minutes (84%).
Total trip7h 10mOAK 20:15 to MDW 05:25, 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.