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

Denver → Milwaukee via Chicago: arrives on time 13%

  1. 17:35 DEN → 21:00 MDW
    WN 1604 · Southwest · 2h 25m · 27% on time, 0.0% cancelled
  2. 55m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:55 MDW → 22:45 MKE
    WN 2043 · Southwest · 50m · 59% on time, 6.1% cancelled

Total trip 4h 10m, scheduled departure to arrival (Milwaukee is 1 h ahead of Denver). Times are local. Both flew on 40 of the last 56 days.

Makes the connection23%The first flight arrived more than 10 minutes late on 77% of the days it flew: too late for the 45-minute minimum connection on a 55m layover.
Arrives on time13%First flight not cancelled (0.0% are) × connection made (23%) × second flight not cancelled (6.1% are) and within 15 minutes (59%).
Total trip4h 10mDEN 17:35 to MKE 22:45, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.