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

Chicago → Pensacola via Dallas: arrives on time 75%

  1. 05:00 MDW → 07:15 DAL
    WN 1377 · Southwest · 2h 15m · 96% on time, 3.8% cancelled
  2. 2h 20m layover in Dallas (DAL) · 45 min minimum on one ticket
  3. 09:35 DAL → 11:25 PNS
    WN 3796 · Southwest · 1h 50m · 79% on time, 2.4% cancelled

Total trip 6h 25m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 95 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 2h 20m layover.
Arrives on time75%First flight not cancelled (3.8% are) × connection made (100%) × second flight not cancelled (2.4% are) and within 15 minutes (79%).
Total trip6h 25mMDW 05:00 to PNS 11:25, 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.