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

Chicago → Milwaukee via New York: arrives on time 85%

  1. 05:15 MDW → 08:15 LGA
    WN 2801 · Southwest · 2h 00m · 93% on time, 0.0% cancelled
  2. 2h 50m layover in New York (LGA) · 90 min minimum on separate tickets
  3. 11:05 LGA → 12:36 MKE
    DL 5723 · Delta, flown by Republic · 2h 35m · 90% on time, 5.5% cancelled

Total trip 7h 25m, scheduled departure to arrival. Times are local. Both flew on 55 of the last 56 days.

Makes the connection100%The first flight arrived more than 80 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 2h 50m layover.
Arrives on time85%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (5.5% are) and within 15 minutes (90%).
Total trip7h 25mMDW 05:15 to MKE 12:36, 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.