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

Boston → Cleveland via Chicago: arrives on time 84%

  1. 07:30 BOS → 09:10 MDW
    WN 745 · Southwest · 2h 40m · 91% on time, 1.8% cancelled
  2. 3h 05m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 12:15 MDW → 14:25 CLE
    WN 1813 · Southwest · 1h 10m · 85% on time, 0.0% cancelled

Total trip 6h 55m, scheduled departure to arrival. Times are local. Both flew on 32 of the last 56 days.

Makes the connection100%The first flight arrived more than 140 minutes late on 0% of the days it flew: too late for the 45-minute minimum connection on a 3h 05m layover.
Arrives on time84%First flight not cancelled (1.8% are) × connection made (100%) × second flight not cancelled (0.0% are) and within 15 minutes (85%).
Total trip6h 55mBOS 07:30 to CLE 14:25, 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.