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

Chicago → New York via Pittsburgh: arrives on time 83%

  1. 07:45 MDW → 10:15 PIT
    WN 846 · Southwest · 1h 30m · 97% on time, 0.0% cancelled
  2. 1h 58m layover in Pittsburgh (PIT) · 90 min minimum on separate tickets
  3. 12:13 PIT → 13:55 JFK
    AA 4568 · American, flown by Republic · 1h 42m · 86% on time, 3.6% cancelled

Total trip 5h 10m, scheduled departure to arrival (New York is 1 h ahead of Chicago). Times are local. Both flew on 56 of the last 56 days.

Makes the connection100%The first flight arrived more than 28 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 1h 58m layover.
Arrives on time83%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (3.6% are) and within 15 minutes (86%).
Total trip5h 10mMDW 07:45 to JFK 13:55, 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.