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

San Jose → Chicago via Seattle: arrives on time 60%

  1. 21:35 SJC → 21:30 SEA
    WN 3705 · Southwest · 2h 10m · 64% on time, 0.0% cancelled
  2. 1h 35m layover in Seattle (SEA) · 45 min minimum on one ticket
  3. 23:05 SEA → 05:00 MDW +1 day
    WN 2304 · Southwest · 3h 55m · 67% on time, 0.0% cancelled

Total trip 5h 25m, scheduled departure to arrival (Chicago is 2 h ahead of San Jose). Times are local. Both flew on 56 of the last 56 days.

Makes the connection90%The first flight arrived more than 50 minutes late on 10% of the days it flew: too late for the 45-minute minimum connection on a 1h 35m layover.
Arrives on time60%First flight not cancelled (0.0% are) × connection made (90%) × second flight not cancelled (0.0% are) and within 15 minutes (67%).
Total trip5h 25mSJC 21:35 to MDW 05:00, 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.