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

San Diego → Chicago via Oakland: arrives on time 35%

  1. 21:00 SAN → 22:35 OAK
    WN 4841 · Southwest · 1h 35m · 44% on time, 0.0% cancelled
  2. 1h 20m layover in Oakland (OAK) · 45 min minimum on one ticket
  3. 23:55 OAK → 06:00 MDW +1 day
    WN 3059 · Southwest · 4h 05m · 66% on time, 0.0% cancelled

Total trip 7h 00m, scheduled departure to arrival (Chicago is 2 h ahead of San Diego). Times are local. Both flew on 43 of the last 56 days.

Makes the connection53%The first flight arrived more than 35 minutes late on 47% of the days it flew: too late for the 45-minute minimum connection on a 1h 20m layover.
Arrives on time35%First flight not cancelled (0.0% are) × connection made (53%) × second flight not cancelled (0.0% are) and within 15 minutes (66%).
Total trip7h 00mSAN 21:00 to MDW 06:00, 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.