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

Orlando → Oakland via Chicago: arrives on time 14%

  1. 18:55 MCO → 20:50 MDW
    WN 2660 · Southwest · 2h 55m · 38% on time, 1.8% cancelled
  2. 50m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:40 MDW → 00:15 OAK +1 day
    WN 4042 · Southwest · 4h 30m · 48% on time, 2.9% cancelled

Total trip 8h 15m, scheduled departure to arrival (Oakland is 3 h behind Orlando). Times are local. Both flew on 32 of the last 56 days.

Makes the connection31%The first flight arrived more than 5 minutes late on 69% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time14%First flight not cancelled (1.8% are) × connection made (31%) × second flight not cancelled (2.9% are) and within 15 minutes (48%).
Total trip8h 15mMCO 18:55 to OAK 00:15, 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.