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

Boston → Milwaukee via Chicago: arrives on time 33%

  1. 13:14 BOS → 15:10 ORD
    AA 547 · American · 2h 56m · 74% on time, 0.0% cancelled
  2. 1h 45m layover in Chicago (ORD) · 45 min minimum on one ticket
  3. 16:55 ORD → 17:49 MKE
    AA 6273 · American, flown by SkyWest · 54m · 37% on time, 0.0% cancelled

Total trip 5h 35m, scheduled departure to arrival (Milwaukee is 1 h behind Boston). Times are local. Both flew on 0 of the last 56 days, too few to list among the best connections.

Makes the connection90%The first flight arrived more than 60 minutes late on 10% of the days it flew: too late for the 45-minute minimum connection on a 1h 45m layover.
Arrives on time33%First flight not cancelled (0.0% are) × connection made (90%) × second flight not cancelled (0.0% are) and within 15 minutes (37%).
Total trip5h 35mBOS 13:14 to MKE 17:49, 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.