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

Chicago → Boston via St Louis: arrives on time 76%

  1. 07:50 MDW → 09:10 STL
    WN 2900 · Southwest · 1h 20m · 95% on time, 0.0% cancelled
  2. 55m layover in St Louis (STL) · 45 min minimum on one ticket
  3. 10:05 STL → 13:40 BOS
    WN 3891 · Southwest · 2h 35m · 82% on time, 0.0% cancelled

Total trip 4h 50m, 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 connection93%The first flight arrived more than 10 minutes late on 7% of the days it flew: too late for the 45-minute minimum connection on a 55m layover.
Arrives on time76%First flight not cancelled (0.0% are) × connection made (93%) × second flight not cancelled (0.0% are) and within 15 minutes (82%).
Total trip4h 50mMDW 07:50 to BOS 13:40, 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.