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

Chicago → San Antonio via Dallas: arrives on time 29%

  1. 16:20 MDW → 18:35 DAL
    WN 2758 · Southwest · 2h 15m · 52% on time, 4.8% cancelled
  2. 1h 20m layover in Dallas (DAL) · 45 min minimum on one ticket
  3. 19:55 DAL → 21:00 SAT
    WN 4415 · Southwest · 1h 05m · 39% on time, 0.0% cancelled

Total trip 4h 40m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection78%The first flight arrived more than 35 minutes late on 22% of the days it flew: too late for the 45-minute minimum connection on a 1h 20m layover.
Arrives on time29%First flight not cancelled (4.8% are) × connection made (78%) × second flight not cancelled (0.0% are) and within 15 minutes (39%).
Total trip4h 40mMDW 16:20 to SAT 21:00, 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.