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

Jacksonville → Chicago via Dallas: arrives on time 35%

  1. 14:50 JAX → 16:15 DAL
    WN 4585 · Southwest · 2h 25m · 61% on time, 0.0% cancelled
  2. 3h 35m layover in Dallas (DAL) · 45 min minimum on one ticket
  3. 19:50 DAL → 22:00 MDW
    WN 107 · Southwest · 2h 15m · 36% on time, 0.0% cancelled

Total trip 8h 15m, scheduled departure to arrival (Chicago is 1 h behind Jacksonville). Times are local. Both flew on 31 of the last 56 days.

Makes the connection97%The first flight arrived more than 170 minutes late on 3% of the days it flew: too late for the 45-minute minimum connection on a 3h 35m layover.
Arrives on time35%First flight not cancelled (0.0% are) × connection made (97%) × second flight not cancelled (0.0% are) and within 15 minutes (36%).
Total trip8h 15mJAX 14:50 to MDW 22:00, 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.