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

Pensacola → Chicago via Washington: arrives on time 73%

  1. 06:00 PNS → 09:29 DCA
    AA 5424 · American, flown by PSA · 2h 29m · 84% on time, 4.1% cancelled
  2. 2h 31m layover in Washington (DCA) · 90 min minimum on separate tickets
  3. 12:00 DCA → 13:00 MDW
    WN 1445 · Southwest · 2h 00m · 85% on time, 0.0% cancelled

Total trip 7h 00m, scheduled departure to arrival. Times are local. Both flew on 39 of the last 56 days.

Makes the connection89%The first flight arrived more than 61 minutes late on 11% of the days it flew: too late for the 90-minute minimum connection on a 2h 31m layover.
Arrives on time73%First flight not cancelled (4.1% are) × connection made (89%) × second flight not cancelled (0.0% are) and within 15 minutes (85%).
Total trip7h 00mPNS 06:00 to MDW 13:00, 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.