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

Pensacola → Chicago via Dallas: arrives on time 71%

  1. 07:00 PNS → 08:45 DAL
    WN 3393 · Southwest · 1h 45m · 92% on time, 3.8% cancelled
  2. 1h 20m layover in Dallas (DAL) · 45 min minimum on one ticket
  3. 10:05 DAL → 12:20 MDW
    WN 1357 · Southwest · 2h 15m · 85% on time, 4.8% cancelled

Total trip 5h 20m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection92%The first flight arrived more than 35 minutes late on 8% of the days it flew: too late for the 45-minute minimum connection on a 1h 20m layover.
Arrives on time71%First flight not cancelled (3.8% are) × connection made (92%) × second flight not cancelled (4.8% are) and within 15 minutes (85%).
Total trip5h 20mPNS 07:00 to MDW 12:20, 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.