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

Portland → Chicago via Washington: arrives on time 76%

  1. 05:45 PWM → 07:45 DCA
    AA 4351 · American, flown by Republic · 1h 59m · 98% on time, 7.8% cancelled
  2. 1h 40m layover in Washington (DCA) · 90 min minimum on separate tickets
  3. 09:25 DCA → 10:20 MDW
    WN 1444 · Southwest · 1h 55m · 86% on time, 0.0% cancelled

Total trip 5h 35m, scheduled departure to arrival (Chicago is 1 h behind Portland). Times are local. Both flew on 40 of the last 56 days.

Makes the connection96%The first flight arrived more than 10 minutes late on 4% of the days it flew: too late for the 90-minute minimum connection on a 1h 40m layover.
Arrives on time76%First flight not cancelled (7.8% are) × connection made (96%) × second flight not cancelled (0.0% are) and within 15 minutes (86%).
Total trip5h 35mPWM 05:45 to MDW 10:20, 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.