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

New Orleans → Chicago via Orlando: arrives on time 74%

  1. 05:00 MSY → 07:50 MCO
    WN 4663 · Southwest · 1h 50m · 91% on time, 1.7% cancelled
  2. 1h 20m layover in Orlando (MCO) · 45 min minimum on one ticket
  3. 09:10 MCO → 10:55 MDW
    WN 4037 · Southwest · 2h 45m · 80% on time, 3.8% cancelled

Total trip 5h 55m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection98%The first flight arrived more than 35 minutes late on 2% of the days it flew: too late for the 45-minute minimum connection on a 1h 20m layover.
Arrives on time74%First flight not cancelled (1.7% are) × connection made (98%) × second flight not cancelled (3.8% are) and within 15 minutes (80%).
Total trip5h 55mMSY 05:00 to MDW 10:55, 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.