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

Boston → Portland via Chicago: arrives on time 42%

  1. 16:45 BOS → 18:35 MDW
    WN 4106 · Southwest · 2h 50m · 54% on time, 2.4% cancelled
  2. 3h 00m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 21:35 MDW → 23:35 PDX
    WN 2852 · Southwest · 4h 20m · 45% on time, 3.5% cancelled

Total trip 10h 10m, scheduled departure to arrival (Portland is 3 h behind Boston). Times are local. Both flew on 40 of the last 56 days.

Makes the connection98%The first flight arrived more than 135 minutes late on 2% of the days it flew: too late for the 45-minute minimum connection on a 3h 00m layover.
Arrives on time42%First flight not cancelled (2.4% are) × connection made (98%) × second flight not cancelled (3.5% are) and within 15 minutes (45%).
Total trip10h 10mBOS 16:45 to PDX 23:35, 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.