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

Boston → Milwaukee via Chicago: arrives on time 47%

  1. 13:56 BOS → 15:59 ORD
    AA 3711 · American, flown by Envoy · 3h 05m · 81% on time, 2.8% cancelled
  2. 4h 00m layover in Chicago (ORD) · 45 min minimum on one ticket
  3. 19:59 ORD → 21:01 MKE
    AA 4888 · American, flown by SkyWest · 1h 02m · 53% on time, 5.6% cancelled

Total trip 8h 05m, scheduled departure to arrival (Milwaukee is 1 h behind Boston). Times are local. Both flew on 56 of the last 56 days.

Makes the connection97%The first flight arrived more than 195 minutes late on 3% of the days it flew: too late for the 45-minute minimum connection on a 4h 00m layover.
Arrives on time47%First flight not cancelled (2.8% are) × connection made (97%) × second flight not cancelled (5.6% are) and within 15 minutes (53%).
Total trip8h 05mBOS 13:56 to MKE 21:01, 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.