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

Boston → Cleveland via Chicago: arrives on time 85%

  1. 05:25 BOS → 07:00 MDW
    WN 3239 · Southwest · 2h 35m · 91% on time, 0.0% cancelled
  2. 55m layover in Chicago (MDW) · 45 min minimum on one ticket
  3. 07:55 MDW → 10:10 CLE
    WN 4088 · Southwest · 1h 15m · 93% on time, 0.0% cancelled

Total trip 4h 45m, scheduled departure to arrival. Times are local. Both flew on 31 of the last 56 days.

Makes the connection91%The first flight arrived more than 10 minutes late on 9% of the days it flew: too late for the 45-minute minimum connection on a 55m layover.
Arrives on time85%First flight not cancelled (0.0% are) × connection made (91%) × second flight not cancelled (0.0% are) and within 15 minutes (93%).
Total trip4h 45mBOS 05:25 to CLE 10:10, 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.