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

Chicago → Portland via Baltimore: arrives on time 43%

  1. 17:20 MDW → 20:15 BWI
    WN 4616 · Southwest · 1h 55m · 44% on time, 0.0% cancelled
  2. 2h 20m layover in Baltimore (BWI) · 45 min minimum on one ticket
  3. 22:35 BWI → 00:10 PWM +1 day
    WN 4382 · Southwest · 1h 35m · 56% on time, 5.2% cancelled

Total trip 5h 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 connection80%The first flight arrived more than 95 minutes late on 20% of the days it flew: too late for the 45-minute minimum connection on a 2h 20m layover.
Arrives on time43%First flight not cancelled (0.0% are) × connection made (80%) × second flight not cancelled (5.2% are) and within 15 minutes (56%).
Total trip5h 50mMDW 17:20 to PWM 00:10, 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.