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

Chicago → San Jose via Phoenix: arrives on time 96%

  1. 05:20 MDW → 06:55 PHX
    WN 2858 · Southwest · 3h 35m · 88% on time, 0.0% cancelled
  2. 2h 45m layover in Phoenix (PHX) · 45 min minimum on one ticket
  3. 09:40 PHX → 11:35 SJC
    WN 3336 · Southwest · 1h 55m · 96% on time, 0.0% cancelled

Total trip 8h 15m, scheduled departure to arrival (San Jose is 2 h behind Chicago). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 120 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 2h 45m layover.
Arrives on time96%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (96%).
Total trip8h 15mMDW 05:20 to SJC 11:35, 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.