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

Oakland → Chicago via Las Vegas: arrives on time 62%

  1. 20:45 OAK → 22:20 LAS
    WN 4503 · Southwest · 1h 35m · 42% on time, 0.0% cancelled
  2. 1h 35m 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 6h 40m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 55 of the last 56 days.

Makes the connection74%The first flight arrived more than 50 minutes late on 26% of the days it flew: too late for the 45-minute minimum connection on a 1h 35m layover.
Arrives on time62%First flight not cancelled (0.0% are) × connection made (74%) × second flight not cancelled (0.0% are) and within 15 minutes (84%).
Total trip6h 40mOAK 20:45 to MDW 05:25, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.