tailodds FORECAST
Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Chicago → Orlando via Cleveland: arrives on time 88%

  1. 07:55 MDW → 10:10 CLE
    WN 4088 · Southwest · 1h 15m · 93% on time, 0.0% cancelled
  2. 2h 06m layover in Cleveland (CLE) · 90 min minimum on separate tickets
  3. 12:16 CLE → 14:43 MCO
    UA 1488 · United · 2h 27m · 92% on time, 0.0% cancelled

Total trip 5h 48m, scheduled departure to arrival (Orlando is 1 h ahead of Chicago). Times are local. Both flew on 38 of the last 56 days.

Makes the connection95%The first flight arrived more than 36 minutes late on 5% of the days it flew: too late for the 90-minute minimum connection on a 2h 06m layover.
Arrives on time88%First flight not cancelled (0.0% are) × connection made (95%) × second flight not cancelled (0.0% are) and within 15 minutes (92%).
Total trip5h 48mMDW 07:55 to MCO 14:43, 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.