tailodds FORECAST
Connection · two tickets · schedule Jun 6 – Jul 31, 2026 · records Aug 2025 – Jul 2026

Chicago → Cleveland via Boston: arrives on time 85%

  1. 09:10 MDW → 12:28 BOS
    WN 1405 · Southwest · 2h 18m · 92% on time, 0.0% cancelled
  2. 2h 26m layover in Boston (BOS) · 90 min minimum on separate tickets
  3. 14:54 BOS → 17:06 CLE
    DL 5641 · Delta, flown by Republic · 2h 12m · 86% on time, 1.1% cancelled

Total trip 6h 56m, scheduled departure to arrival (Cleveland is 1 h ahead of Chicago). Times are local. Both flew on 48 of the last 56 days.

Makes the connection100%The first flight arrived more than 56 minutes late on 0% of the days it flew: too late for the 90-minute minimum connection on a 2h 26m layover.
Arrives on time85%First flight not cancelled (0.0% are) × connection made (100%) × second flight not cancelled (1.1% are) and within 15 minutes (86%).
Total trip6h 56mMDW 09:10 to CLE 17:06, 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.