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

Orlando → Milwaukee via Chicago: arrives on time 22%

  1. 18:55 MCO → 20:50 MDW
    WN 2660 · Southwest · 2h 55m · 38% on time, 1.8% cancelled
  2. 1h 05m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:55 MDW → 22:45 MKE
    WN 2043 · Southwest · 50m · 59% on time, 6.1% cancelled

Total trip 4h 50m, scheduled departure to arrival (Milwaukee is 1 h behind Orlando). Times are local. Both flew on 47 of the last 56 days.

Makes the connection40%The first flight arrived more than 20 minutes late on 60% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time22%First flight not cancelled (1.8% are) × connection made (40%) × second flight not cancelled (6.1% are) and within 15 minutes (59%).
Total trip4h 50mMCO 18:55 to MKE 22:45, 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.