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 9%

  1. 17:00 SJC → 18:30 LAS
    WN 2266 · Southwest · 1h 30m · 57% on time, 0.0% cancelled
  2. 50m layover in Las Vegas (LAS) · 45 min minimum on one ticket
  3. 19:20 LAS → 01:30 MDW +1 day
    WN 3200 · Southwest · 3h 35m · 28% on time, 0.0% cancelled

Total trip 5h 55m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 40 of the last 56 days.

Makes the connection33%The first flight arrived more than 5 minutes late on 67% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time9%First flight not cancelled (0.0% are) × connection made (33%) × second flight not cancelled (0.0% are) and within 15 minutes (28%).
Total trip5h 55mSJC 17:00 to MDW 01:30, 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.