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

Cleveland → Chicago via St Louis: arrives on time 82%

  1. 07:05 CLE → 07:40 STL
    WN 1165 · Southwest · 1h 35m · 90% on time, 0.0% cancelled
  2. 1h 15m 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 3h 55m, scheduled departure to arrival (Chicago is 1 h behind Cleveland). Times are local. Both flew on 32 of the last 56 days.

Makes the connection93%The first flight arrived more than 30 minutes late on 7% of the days it flew: too late for the 45-minute minimum connection on a 1h 15m layover.
Arrives on time82%First flight not cancelled (0.0% are) × connection made (93%) × second flight not cancelled (0.0% are) and within 15 minutes (88%).
Total trip3h 55mCLE 07:05 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.