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

Portland → Boston via Chicago: arrives on time 88%

  1. 22:59 PDX → 05:00 ORD
    AS 376 · Alaska · 4h 01m · 87% on time, 2.7% cancelled
  2. 3h 30m layover in Chicago (ORD) · 90 min minimum on separate tickets
  3. 08:30 ORD → 12:07 BOS +1 day
    AA 4106 · American, flown by Envoy · 2h 37m · 91% on time, 0.0% cancelled

Total trip 10h 08m, scheduled departure to arrival (Boston is 3 h ahead of Portland). Times are local. Both flew on 50 of the last 56 days.

Makes the connection99%The first flight arrived more than 120 minutes late on 1% of the days it flew: too late for the 90-minute minimum connection on a 3h 30m layover.
Arrives on time88%First flight not cancelled (2.7% are) × connection made (99%) × second flight not cancelled (0.0% are) and within 15 minutes (91%).
Total trip10h 08mPDX 22:59 to BOS 12:07, 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.