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

Portland → Orlando via Chicago: arrives on time 81%

  1. 23:30 PDX → 05:20 MDW
    WN 3203 · Southwest · 3h 50m · 89% on time, 1.7% cancelled
  2. 1h 10m 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 7h 35m, scheduled departure to arrival (Orlando is 3 h ahead of Portland). Times are local. Both flew on 39 of the last 56 days.

Makes the connection91%The first flight arrived more than 25 minutes late on 9% of the days it flew: too late for the 45-minute minimum connection on a 1h 10m layover.
Arrives on time81%First flight not cancelled (1.7% are) × connection made (91%) × second flight not cancelled (0.0% are) and within 15 minutes (90%).
Total trip7h 35mPDX 23:30 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.