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

Chicago → Orlando via Phoenix: arrives on time 22%

  1. 20:35 MDW → 22:15 PHX
    WN 2863 · Southwest · 3h 40m · 48% on time, 8.0% cancelled
  2. 50m layover in Phoenix (PHX) · 45 min minimum on one ticket
  3. 23:05 PHX → 06:20 MCO +1 day
    WN 4508 · Southwest · 4h 15m · 81% on time, 1.7% cancelled

Total trip 8h 45m, scheduled departure to arrival (Orlando is 1 h ahead of Chicago). Times are local. Both flew on 48 of the last 56 days.

Makes the connection30%The first flight arrived more than 5 minutes late on 70% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time22%First flight not cancelled (8.0% are) × connection made (30%) × second flight not cancelled (1.7% are) and within 15 minutes (81%).
Total trip8h 45mMDW 20:35 to MCO 06:20, 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.