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

Chicago → Portland via Baltimore: arrives on time 77%

  1. 08:55 MDW → 11:45 BWI
    WN 1355 · Southwest · 1h 50m · 90% on time, 0.0% cancelled
  2. 3h 30m layover in Baltimore (BWI) · 45 min minimum on one ticket
  3. 15:15 BWI → 16:45 PWM
    WN 297 · Southwest · 1h 30m · 80% on time, 3.8% cancelled

Total trip 6h 50m, scheduled departure to arrival (Portland is 1 h ahead of Chicago). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 165 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 30m layover.
Arrives on time77%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (3.8% are) and within 15 minutes (80%).
Total trip6h 50mMDW 08:55 to PWM 16:45, 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.