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

Boston → Chicago via Dallas: arrives on time 19%

  1. 17:45 BOS → 20:55 DAL
    WN 737 · Southwest · 4h 10m · 39% on time, 3.4% cancelled
  2. 1h 27m layover in Dallas (DAL) · 45 min minimum on one ticket
  3. 22:22 DAL → 01:00 MDW +1 day
    WN 1359 · Southwest · 2h 15m · 34% on time, 6.0% cancelled

Total trip 7h 52m, scheduled departure to arrival (Chicago is 1 h behind Boston). Times are local. Both flew on 48 of the last 56 days.

Makes the connection60%The first flight arrived more than 42 minutes late on 40% of the days it flew: too late for the 45-minute minimum connection on a 1h 27m layover.
Arrives on time19%First flight not cancelled (3.4% are) × connection made (60%) × second flight not cancelled (6.0% are) and within 15 minutes (34%).
Total trip7h 52mBOS 17:45 to MDW 01:00, layover included

Tight connection: often missed. The first flight is late enough to miss it on more than 1 day in 4.

Not yet counted: the second flight also leaving late (which helps), gate-to-gate distance at the hub, and rebooking after a missed connection.