Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
San Diego → Chicago via Orlando: arrives on time 92%
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21:55 SAN → 05:55 MCOWN 4874 · Southwest · 5h 00m · 70% on time, 1.7% cancelled
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2h 05m layover in Orlando (MCO) · 45 min minimum on one ticket
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08:00 MCO → 09:50 MDW +1 dayWN 2835 · Southwest · 2h 50m · 97% on time, 3.1% cancelled
Total trip 9h 55m, scheduled departure to arrival (Chicago is 2 h ahead of San Diego). Times are local. Both flew on 31 of the last 56 days.
Makes the connection100%The first flight arrived more than 80 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 2h 05m layover.
Arrives on time92%First flight not cancelled (1.7% are) × connection made (100%) × second flight not cancelled (3.1% are) and within 15 minutes (97%).
Total trip9h 55mSAN 21:55 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.