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

Chicago → Milwaukee via St Louis: arrives on time 66%

  1. 18:00 MDW → 19:10 STL
    WN 2904 · Southwest · 1h 10m · 70% on time, 4.8% cancelled
  2. 2h 35m layover in St Louis (STL) · 45 min minimum on one ticket
  3. 21:45 STL → 22:55 MKE
    WN 3406 · Southwest · 1h 10m · 71% on time, 0.0% cancelled

Total trip 4h 55m, scheduled departure to arrival. Times are local. Both flew on 40 of the last 56 days.

Makes the connection98%The first flight arrived more than 110 minutes late on 3% of the days it flew: too late for the 45-minute minimum connection on a 2h 35m layover.
Arrives on time66%First flight not cancelled (4.8% are) × connection made (98%) × second flight not cancelled (0.0% are) and within 15 minutes (71%).
Total trip4h 55mMDW 18:00 to MKE 22:55, 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.