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

Chicago → Pensacola via Miami: arrives on time 81%

08:30 MDW → 12:30 MIA

WN 2464 · Southwest · 3h 00m · 66% on time, 0.0% cancelled
3h 01m layover in Miami (MIA) · 90 min minimum on separate tickets
15:31 MIA → 16:34 PNS

AA 3749 · American, flown by Envoy · 1h 57m · 81% on time, 0.0% cancelled

Total trip 7h 58m, scheduled departure to arrival. Times are local. Both flew on 48 of the last 56 days.

Makes the connection100%The first flight arrived more than 91 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 01m layover.

Arrives on time81%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (81%).

Total trip7h 58mMDW 08:30 to PNS 16:34, 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.