tailodds FORECAST
Connection · one ticket · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Portland → Chicago via Baltimore: arrives on time 24%

  1. 17:20 PWM → 19:05 BWI
    WN 3414 · Southwest · 1h 45m · 76% on time, 5.3% cancelled
  2. 1h 50m layover in Baltimore (BWI) · 45 min minimum on one ticket
  3. 20:55 BWI → 22:00 MDW
    WN 999 · Southwest · 2h 05m · 28% on time, 4.9% cancelled

Total trip 5h 40m, scheduled departure to arrival (Chicago is 1 h behind Portland). Times are local. Both flew on 39 of the last 56 days.

Makes the connection94%The first flight arrived more than 65 minutes late on 6% of the days it flew: too late for the 45-minute minimum connection on a 1h 50m layover.
Arrives on time24%First flight not cancelled (5.3% are) × connection made (94%) × second flight not cancelled (4.9% are) and within 15 minutes (28%).
Total trip5h 40mPWM 17:20 to MDW 22:00, 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.