Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026
San Jose → Chicago via Denver: arrives on time 47%
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10:25 SJC → 13:50 DENWN 3666 · Southwest · 2h 25m · 59% on time, 0.0% cancelled
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1h 10m layover in Denver (DEN) · 45 min minimum on one ticket
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15:00 DEN → 18:20 MDWWN 1603 · Southwest · 2h 20m · 61% on time, 3.4% cancelled
Total trip 5h 55m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 32 of the last 56 days.
Makes the connection79%The first flight arrived more than 25 minutes late on 21% of the days it flew: too late for the 45-minute minimum connection on a 1h 10m layover.
Arrives on time47%First flight not cancelled (0.0% are) × connection made (79%) × second flight not cancelled (3.4% are) and within 15 minutes (61%).
Total trip5h 55mSJC 10:25 to MDW 18:20, 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.