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

Chicago → Portland via Charlotte: arrives on time 79%

  1. 07:50 MDW → 10:55 CLT
    WN 2749 · Southwest · 2h 05m · 96% on time, 0.0% cancelled
  2. 3h 58m layover in Charlotte (CLT) · 90 min minimum on separate tickets
  3. 14:53 CLT → 17:09 PWM
    AA 2352 · American · 2h 16m · 79% on time, 0.0% cancelled

Total trip 8h 19m, scheduled departure to arrival (Portland is 1 h ahead of Chicago). Times are local. Both flew on 46 of the last 56 days.

Makes the connection100%The first flight arrived more than 148 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 58m layover.
Arrives on time79%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (79%).
Total trip8h 19mMDW 07:50 to PWM 17:09, 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.