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

Orlando → Oakland via Chicago: arrives on time 62%

  1. 07:25 MCO → 09:15 MDW
    WN 2654 · Southwest · 2h 50m · 88% on time, 0.0% cancelled
  2. 50m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 10:05 MDW → 12:35 OAK
    WN 3366 · Southwest · 4h 30m · 74% on time, 0.0% cancelled

Total trip 8h 10m, scheduled departure to arrival (Oakland is 3 h behind Orlando). Times are local. Both flew on 32 of the last 56 days.

Makes the connection83%The first flight arrived more than 5 minutes late on 17% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time62%First flight not cancelled (0.0% are) × connection made (83%) × second flight not cancelled (0.0% are) and within 15 minutes (74%).
Total trip8h 10mMCO 07:25 to OAK 12:35, 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.