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

San Diego → Chicago via Orlando: arrives on time 92%

  1. 21:06 SAN → 05:18 MCO
    AS 707 · Alaska · 5h 12m · 87% on time, 1.0% cancelled
  2. 2h 42m layover in Orlando (MCO) · 90 min minimum on separate tickets
  3. 08:00 MCO → 09:50 MDW +1 day
    WN 2835 · Southwest · 2h 50m · 97% on time, 3.1% cancelled

Total trip 10h 44m, scheduled departure to arrival (Chicago is 2 h ahead of San Diego). Times are local. Both flew on 30 of the last 56 days.

Makes the connection99%The first flight arrived more than 72 minutes late on 1% of the days it flew: too late for the 90-minute minimum connection on a 2h 42m layover.
Arrives on time92%First flight not cancelled (1.0% are) × connection made (99%) × second flight not cancelled (3.1% are) and within 15 minutes (97%).
Total trip10h 44mSAN 21:06 to MDW 09:50, 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.