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

Boston → Chicago via Denver: arrives on time 83%

  1. 06:25 BOS → 08:50 DEN
    WN 4156 · Southwest · 4h 25m · 88% on time, 0.0% cancelled
  2. 1h 10m layover in Denver (DEN) · 45 min minimum on one ticket
  3. 10:00 DEN → 13:25 MDW
    WN 755 · Southwest · 2h 25m · 89% on time, 1.8% cancelled

Total trip 8h 00m, scheduled departure to arrival (Chicago is 1 h behind Boston). Times are local. Both flew on 55 of the last 56 days.

Makes the connection95%The first flight arrived more than 25 minutes late on 5% of the days it flew: too late for the 45-minute minimum connection on a 1h 10m layover.
Arrives on time83%First flight not cancelled (0.0% are) × connection made (95%) × second flight not cancelled (1.8% are) and within 15 minutes (89%).
Total trip8h 00mBOS 06:25 to MDW 13:25, 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.