tailodds FORECAST
Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Dallas-Fort Worth → Chicago via Pensacola: arrives on time 79%

  1. 07:00 DFW → 08:57 PNS
    AA 3748 · American, flown by Envoy · 1h 57m · 83% on time, 0.0% cancelled
  2. 1h 43m layover in Pensacola (PNS) · 90 min minimum on separate tickets
  3. 10:40 PNS → 12:55 MDW
    WN 2866 · Southwest · 2h 15m · 96% on time, 0.0% cancelled

Total trip 5h 55m, scheduled departure to arrival. Times are local. Both flew on 24 of the last 56 days.

Makes the connection82%The first flight arrived more than 13 minutes late on 18% of the days it flew: too late for the 90-minute minimum connection on a 1h 43m layover.
Arrives on time79%First flight not cancelled (0.0% are) × connection made (82%) × second flight not cancelled (0.0% are) and within 15 minutes (96%).
Total trip5h 55mDFW 07:00 to MDW 12:55, 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.