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

Boston → Chicago via St Louis: arrives on time 88%

  1. 05:50 BOS → 07:45 STL
    WN 752 · Southwest · 2h 55m · 100% on time, 0.0% cancelled
  2. 1h 10m layover in St Louis (STL) · 45 min minimum on one ticket
  3. 08:55 STL → 10:00 MDW
    WN 2570 · Southwest · 1h 05m · 88% on time, 0.0% cancelled

Total trip 5h 10m, scheduled departure to arrival (Chicago is 1 h behind Boston). Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 25 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 1h 10m layover.
Arrives on time88%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (88%).
Total trip5h 10mBOS 05:50 to MDW 10:00, 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.