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

Chicago → Portland via Philadelphia: arrives on time 87%

  1. 07:40 MDW → 10:42 PHL
    WN 4122 · Southwest · 2h 02m · 94% on time, 0.0% cancelled
  2. 2h 03m layover in Philadelphia (PHL) · 90 min minimum on separate tickets
  3. 12:45 PHL → 14:16 PWM
    AA 2354 · American · 1h 31m · 89% on time, 0.0% cancelled

Total trip 5h 36m, scheduled departure to arrival (Portland is 1 h ahead of Chicago). Times are local. Both flew on 48 of the last 56 days.

Makes the connection98%The first flight arrived more than 33 minutes late on 2% of the days it flew: too late for the 90-minute minimum connection on a 2h 03m layover.
Arrives on time87%First flight not cancelled (0.0% are) × connection made (98%) × second flight not cancelled (0.0% are) and within 15 minutes (89%).
Total trip5h 36mMDW 07:40 to PWM 14:16, 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.