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

Chicago → San Jose via San Diego: arrives on time 93%

  1. 05:52 MDW → 08:00 SAN
    WN 3103 · Southwest · 4h 08m · 94% on time, 0.0% cancelled
  2. 1h 30m layover in San Diego (SAN) · 45 min minimum on one ticket
  3. 09:30 SAN → 11:00 SJC
    WN 4509 · Southwest · 1h 30m · 93% on time, 0.0% cancelled

Total trip 7h 08m, scheduled departure to arrival (San Jose is 2 h behind Chicago). Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 45 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 1h 30m layover.
Arrives on time93%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (93%).
Total trip7h 08mMDW 05:52 to SJC 11:00, 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.