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

Dallas → Orlando via Chicago: arrives on time 28%

  1. 14:05 DAL → 16:20 MDW
    WN 1358 · Southwest · 2h 15m · 60% on time, 4.0% cancelled
  2. 50m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 17:10 MDW → 20:55 MCO
    WN 164 · Southwest · 2h 45m · 75% on time, 7.7% cancelled

Total trip 5h 50m, scheduled departure to arrival (Orlando is 1 h ahead of Dallas). Times are local. Both flew on 24 of the last 56 days.

Makes the connection42%The first flight arrived more than 5 minutes late on 58% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time28%First flight not cancelled (4.0% are) × connection made (42%) × second flight not cancelled (7.7% are) and within 15 minutes (75%).
Total trip5h 50mDAL 14:05 to MCO 20:55, 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.