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

Chicago → San Jose via Baltimore: arrives on time 48%

  1. 08:55 MDW → 11:45 BWI
    WN 1355 · Southwest · 1h 50m · 90% on time, 0.0% cancelled
  2. 1h 05m layover in Baltimore (BWI) · 45 min minimum on one ticket
  3. 12:50 BWI → 15:25 SJC
    WN 186 · Southwest · 5h 35m · 51% on time, 2.4% cancelled

Total trip 8h 30m, scheduled departure to arrival (San Jose is 2 h behind Chicago). Times are local. Both flew on 40 of the last 56 days.

Makes the connection95%The first flight arrived more than 20 minutes late on 5% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time48%First flight not cancelled (0.0% are) × connection made (95%) × second flight not cancelled (2.4% are) and within 15 minutes (51%).
Total trip8h 30mMDW 08:55 to SJC 15:25, 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.