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

Oakland → Chicago via Houston: arrives on time 16%

  1. 13:55 OAK → 19:40 HOU
    WN 4244 · Southwest · 3h 45m · 31% on time, 0.0% cancelled
  2. 1h 05m layover in Houston (HOU) · 45 min minimum on one ticket
  3. 20:45 HOU → 23:10 MDW
    WN 2044 · Southwest · 2h 25m · 38% on time, 1.8% cancelled

Total trip 7h 15m, scheduled departure to arrival (Chicago is 2 h ahead of Oakland). Times are local. Both flew on 24 of the last 56 days.

Makes the connection42%The first flight arrived more than 20 minutes late on 58% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time16%First flight not cancelled (0.0% are) × connection made (42%) × second flight not cancelled (1.8% are) and within 15 minutes (38%).
Total trip7h 15mOAK 13:55 to MDW 23:10, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.