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

San Jose → Chicago via Las Vegas: arrives on time 84%

  1. 18:50 SJC → 20:20 LAS
    WN 2335 · Southwest · 1h 30m · 76% on time, 0.0% cancelled
  2. 3h 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 8h 35m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 170 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 35m layover.
Arrives on time84%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (84%).
Total trip8h 35mSJC 18:50 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.