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

San Jose → Orlando via Chicago: arrives on time 90%

  1. 22:55 SJC → 05:00 MDW
    WN 3886 · Southwest · 4h 05m · 94% on time, 0.0% cancelled
  2. 1h 30m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 06:30 MDW → 10:05 MCO +1 day
    WN 2816 · Southwest · 2h 35m · 90% on time, 0.0% cancelled

Total trip 8h 10m, scheduled departure to arrival (Orlando is 3 h ahead of San Jose). Times are local. Both flew on 31 of the last 56 days.

Makes the connection100%The first flight arrived more than 45 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 1h 30m layover.
Arrives on time90%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (90%).
Total trip8h 10mSJC 22:55 to MCO 10:05, 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.