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

Chicago → Portland via Detroit: arrives on time 87%

  1. 07:55 MDW → 10:05 DTW
    WN 1775 · Southwest · 1h 10m · 85% on time, 0.0% cancelled
  2. 3h 55m layover in Detroit (DTW) · 90 min minimum on separate tickets
  3. 14:00 DTW → 15:55 PWM
    DL 1821 · Delta · 1h 55m · 89% on time, 1.8% cancelled

Total trip 7h 00m, scheduled departure to arrival (Portland is 1 h ahead of Chicago). Times are local. Both flew on 38 of the last 56 days.

Makes the connection100%The first flight arrived more than 145 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 3h 55m layover.
Arrives on time87%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (1.8% are) and within 15 minutes (89%).
Total trip7h 00mMDW 07:55 to PWM 15:55, 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.