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

Chicago → Orlando via Baltimore: arrives on time 58%

  1. 08:55 MDW → 11:45 BWI
    WN 1355 · Southwest · 1h 50m · 90% on time, 0.0% cancelled
  2. 1h 03m layover in Baltimore (BWI) · 45 min minimum on one ticket
  3. 12:48 BWI → 15:10 MCO
    WN 4374 · Southwest · 2h 22m · 62% on time, 0.0% cancelled

Total trip 5h 15m, scheduled departure to arrival (Orlando is 1 h ahead of Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection93%The first flight arrived more than 18 minutes late on 7% of the days it flew: too late for the 45-minute minimum connection on a 1h 03m layover.
Arrives on time58%First flight not cancelled (0.0% are) × connection made (93%) × second flight not cancelled (0.0% are) and within 15 minutes (62%).
Total trip5h 15mMDW 08:55 to MCO 15:10, 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.