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

Houston → Chicago via San Diego: arrives on time 33%

  1. 20:40 HOU → 21:50 SAN
    WN 2072 · Southwest · 3h 10m · 57% on time, 0.0% cancelled
  2. 50m layover in San Diego (SAN) · 45 min minimum on one ticket
  3. 22:40 SAN → 04:40 MDW +1 day
    WN 257 · Southwest · 4h 00m · 92% on time, 0.0% cancelled

Total trip 8h 00m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection36%The first flight arrived more than 5 minutes late on 64% of the days it flew: too late for the 45-minute minimum connection on a 50m layover.
Arrives on time33%First flight not cancelled (0.0% are) × connection made (36%) × second flight not cancelled (0.0% are) and within 15 minutes (92%).
Total trip8h 00mHOU 20:40 to MDW 04:40, 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.