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

Chicago → Boston via Denver: arrives on time 10%

  1. 16:15 MDW → 18:00 DEN
    WN 2769 · Southwest · 2h 45m · 62% on time, 1.7% cancelled
  2. 1h 05m layover in Denver (DEN) · 45 min minimum on one ticket
  3. 19:05 DEN → 01:00 BOS +1 day
    WN 1494 · Southwest · 3h 55m · 16% on time, 0.0% cancelled

Total trip 7h 45m, scheduled departure to arrival (Boston is 1 h ahead of Chicago). Times are local. Both flew on 48 of the last 56 days.

Makes the connection64%The first flight arrived more than 20 minutes late on 36% of the days it flew: too late for the 45-minute minimum connection on a 1h 05m layover.
Arrives on time10%First flight not cancelled (1.7% are) × connection made (64%) × second flight not cancelled (0.0% are) and within 15 minutes (16%).
Total trip7h 45mMDW 16:15 to BOS 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.