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

Boston → Portland via Chicago: arrives on time 84%

  1. 05:25 BOS → 07:00 MDW
    WN 3239 · Southwest · 2h 35m · 91% on time, 0.0% cancelled
  2. 3h 05m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 10:05 MDW → 12:25 PDX
    WN 2809 · Southwest · 4h 20m · 84% on time, 0.0% cancelled

Total trip 10h 00m, scheduled departure to arrival (Portland is 3 h behind Boston). Times are local. Both flew on 24 of the last 56 days.

Makes the connection100%The first flight arrived more than 140 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 05m layover.
Arrives on time84%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (84%).
Total trip10h 00mBOS 05:25 to PDX 12:25, 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.